2-methyl-1,3-Cyclohexanedione
(Synonyms: 2-甲基-1,3-环己二酮) 目录号 : GC42178
Synthetic intermediate
Cas No.:1193-55-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-methyl-1,3-Cyclohexanedione is a synthetic intermediate useful for pharmaceutical synthesis.
| Cas No. | 1193-55-1 | SDF | |
| 别名 | 2-甲基-1,3-环己二酮 | ||
| Canonical SMILES | CC1C(=O)CCCC1=O | ||
| 分子式 | C7H10O2 | 分子量 | 126.2 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml,Ethanol: 2 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.9239 mL | 39.6197 mL | 79.2393 mL |
| 5 mM | 1.5848 mL | 7.9239 mL | 15.8479 mL |
| 10 mM | 0.7924 mL | 3.962 mL | 7.9239 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
CH⋯O H-bond mediated tautomerization of 2-methyl-1,3-Cyclohexanedione: A combined IR spectroscopic and theoretical study
Spectrochim Acta A Mol Biomol Spectrosc 2021 May 15;253:119550.PMID:33631624DOI:10.1016/j.saa.2021.119550.
Molecular association and its impact on the keto-enol tautomerization of 2-methyl-1,3-Cyclohexanedione (MCHD) have been investigated in low temperature argon matrix and thin solid film. The system exists exclusively in diketo tautomeric form in argon matrix. The CH⋯O H-bonded homodimers of the diketo tautomer are produced by annealing the matrix at 28 K. No trace of the keto-enol tautomer is observed in matrix isolated homodimers in the temperature range of 8-28 K. However, tautomeric conversion initiates in a thin film of pure diketo tautomer when the temperature of the film is raised to ~170 K. Transition state calculations on the monomeric and dimeric MCHD demonstrate that CH⋯O H-bond formations between diketo tautomers play a vital role in lowering the tautomerization barrier. However, the extent of CH⋯O H-bonded dimer formation in matrix isolation, as well as extent of tautomerization in the neat sample are found to be smaller than that for the previously reported 1,3-cyclohexanedione (CHD) under similar experimental conditions (J. Phys. Chem. A 2012, 116, 3836-3845). Electronic structure calculations suggest that formation of the CH⋯O H-bonded dimer is less feasible in presence of the bulky 2-methyl groups of MCHD, as compared to CHD. Additionally, the transition state geometry of the dimeric keto-enol product of MCHD, as compared to the same for CHD, is more strained and offers a weaker CH---O H-bond that contributes to lesser tautomeric conversion in the former.
Conformational transformation coupled with the order-disorder phase transition in 2-methyl-1,3-Cyclohexanedione crystals
Acta Crystallogr B 2000 Oct;56 ( Pt 5):872-81.PMID:11006563DOI:10.1107/S0108768100005905.
The half-chair conformation of the dynamically disordered molecular ring of 2-methyl-1,3-Cyclohexanedione, C(7)H(10)O(2), transforms to a sofa below Tc = 244 K, when the crystal undergoes a continuous phase transition induced by the onset of halting large-amplitude vibrations of methylene groups C(4)H(2) and C(5)H(2). The temperature dependence of the crystal structure has been investigated by X-ray diffraction. The Ibam symmetry of the crystal reduces below Tc to space group Pccn. The mechanism of the phase transition and of the conversion of the ring conformation is discussed.
Conformational transformation coupled with the order-disorder phase transition in 2-methyl-1,3-Cyclohexanedione crystals. erratum
Acta Crystallogr B 2000 Dec;56 (Pt 6):1112.PMID:11099980DOI:10.1107/s0108768100015196.
In the recently published article by Katrusiak (2000) a misprint occurred in the name of one of the authors in a reference (Wasicki et al., 1995) in the final printing stage. The correct spelling of the name is Wasicki.
How to Start a Total Synthesis from the Wieland-Miescher Ketone?
Curr Org Synth 2019;16(3):328-341.PMID:31984897DOI:10.2174/1570179416666190328233710.
Background: The Wieland-Miescher ketone consists of a couple of enantiomers of 9-methyl- Δ5(10)-octalin-1,6-dione, in which the configuration at 9-position is S- or R-type. The Robinson annulation of 2-methyl-1,3-Cyclohexanedione with methyl vinyl ketone is able to afford the Wieland-Miescher ketone. As widely used in the total synthesis, the Wieland-Miescher ketone is treated at the beginning of total synthesis, and protocols for treating the Wieland-Miescher ketone are worthy to be addressed. Objective: The presented review provides the progress of the usage of Wieland-Miescher ketone for the total synthesis, while treatments on C=C and C=O in the Wieland-Miescher ketone at the beginning of total synthesis are exemplified herein. Conclusion: Modifications of the Wieland-Miescher ketone are composed of oxidation, reduction, and electrophilic or nucleophilic addition. In addition, protection of non-conjugated C=O with glycol or protection of conjugated C=O with ethanedithiol, and the introduction of substituents into α-position of C=C can also be used to modify the structure of the Wieland-Miescher ketone. It is reasonably believed that many novel strategies will be found to treat the Wieland-Miescher ketone in the future total synthesis.
Control of Chemical Reactions by Using Molecules that Buffer Non-aqueous Solutions
Chemistry 2020 Jan 2;26(1):222-229.PMID:31646678DOI:10.1002/chem.201903552.
Control of chemical reactions is necessary to obtain designer chemical transformation products and for preventing decomposition and isomerization reactions of compounds of interest. For the control of chemical events in aqueous solutions, the use of aqueous buffers is a common practice. However, no molecules that buffer non-aqueous solutions were commonly used. Herein, we demonstrate that 1,3-cyclohexanedione derivatives have buffering functions in non-aqueous solutions. It was also shown that these molecules can be utilized to alter and control chemical reactions. 1,3-Cyclohexanedione derivatives inhibited both acid- and base-catalyzed isomerizations and decompositions in organic solvents. The reaction products obtained in the presence of the buffering molecule 2-methyl-1,3-Cyclohexanedione differed from those obtained in the absence of the buffering molecule. The use of buffering molecules that work in organic solvents provides a strategy to control chemical reactions and expands the range of compounds that can be synthesized.