Methyl (1S^*,2R^*,3S^*)-2-<3-(1,2-epoxycyclohexanyl)>acetate | 126059-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Methyl (1S^*,2R^*,3S^*)-2-<3-(1,2-epoxycyclohexanyl)>acetate
• 英文别名: methyl <(1RS,2RS,3SR)-2,3-epoxycyclohexyl>acetate；methyl (cis-1,2-epoxycyclohexan-3-yl)acetate；methyl 2-[(1R,2S,6S)-7-oxabicyclo[4.1.0]heptan-2-yl]acetate
• CAS: 126059-91-4
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: MUKHSWUUZVOJFU-ACLDMZEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (1S^*,2R^*,3S^*)-2-<3-(1,2-epoxycyclohexanyl)>acetate 在 甲醇 、 sodium azide 、 氯化铵 作用下， 生成 (+/-)-methyl 2-(3-azido-2-hydroxycyclohexyl)acetate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of conformationally constrained glycerol 3-phosphate acyltransferase inhibitors

  摘要：

  Glycerol 3-phosphate acyltransferase (GPAT)isozymes are central control points for fat synthesis in mammals. Development of inhibitors of these membrane-bound enzymes could lead to an effective treatment for obesity, but is thwarted by an absence of direct structural information. Based on a highly successful study involving conformationally constrained glycerol 3-phosphate analogs functioning as potent glycerol 3-phosphate dehydrogenase inhibitors, several series of cyclic bisubstrate and transition state analogs were designed, synthesized, and tested as GPAT inhibitors. The weaker in vitro inhibitory activity of these compounds compared to a previously described benzoic acid series was then examined in docking experiments with the soluble squash chloroplast GPAT crystal structure. These in silico experiments indicate that cyclopentyl and cyclohexyl scaffolds prepared in this study may be occluded from the enzyme active site by two protein loops that sterically guard the phosphate binding region. In view of these findings, future GPAT inhibitor design will be driven toward compounds based on planar frameworks able to slide between these loops and enter the active site, resulting in improved inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.091
• 作为产物：
  描述：

  ethyl (cyclohexen-3-yl)acetate 在 sodium hydroxide 、 碘 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 Methyl (1S^*,2R^*,3S^*)-2-<3-(1,2-epoxycyclohexanyl)>acetate
  参考文献：
  名称：

  酮导向的过酸环氧化

  摘要：

  已显示出羰基羰基以比酯所显示的更高的选择性来指导环烯烃的环氧化。一个18 ö标记研究来显示中间双环氧乙烷不参与这些反应。

  DOI：

  10.1016/0040-4039(94)88103-0

文献信息

• Ketone-directed peracid epoxidation of cyclic alkenes
  作者：Alan Armstrong、Paul A. Barsanti、Paul A. Clarke、Anthony Wood

  DOI：10.1039/p19960001373

  日期：——

  Ketone carbonyl groups are shown to direct the peracid epoxidation of cyclic alkenes with greater selectivity than that displayed by esters. An 18O labelling study is used to show that a dioxirane intermediate is not involved in these reactions.

  已显示出羰基羰基以比酯所显示的更大的选择性来指导环状烯烃的过酸环氧化。一个18 ö标记研究来显示中间双环氧乙烷不参与这些反应。
• Diastereoselectivity in the Epoxidation of Substituted Cyclohexenes by Dimethyldioxirane¹^,²
  作者：Robert W. Murray、Megh Singh、Brian L. Williams、Hazel M. Moncrieff

  DOI：10.1021/jo951864j

  日期：1996.1.1

  Three series of compounds based on the cyclohexene framework. have been epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influences on the epoxide stereochemistry.
• Steric control of epoxidation by carbamate and amide groups. Evidence for the carbonyl-directed epoxidation
  作者：Pavel Kocovsky、Ivo Stary

  DOI：10.1021/jo00297a047

  日期：1990.5
• Miyashita, Kazuyuki; Tanaka, Akira; Mizuno, Hiroaki, Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 847 - 852
  作者：Miyashita, Kazuyuki、Tanaka, Akira、Mizuno, Hiroaki、Tanaka, Masahiro、Iwata, Chuzo

  DOI：——

  日期：——
• Diastereoface-Selective Epoxidations: Dependency on the Reagent Electrophilicity
  作者：Charles Fehr

  DOI：10.1002/(sici)1521-3773(19980918)37:17<2407::aid-anie2407>3.0.co;2-w

  日期：1998.9.18

  Substrate-imposed steric constraints can be overriden by the pronounced preference of strong peracids for epoxidation on the π face, which has the highest electron density. For example, the syn:anti ratio for reaction (1) with CF3 CO3 H in CH2 Cl2 is 82:18, that with CH3 CO3 H in toluene is 3:97.