cis-3,4-Epoxycyclohexanecarboxylic acid methyl ester | 1630-01-9

• 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: cis-3,4-Epoxycyclohexanecarboxylic acid methyl ester
• 英文别名: trans-3,4-epoxy-1-methoxycarbonylcyclohexane；methyl t-3,4-epoxy-r-1-cyclohexanecarboxylate；methyl (1S,3R,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylate
• CAS: 1630-01-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: QCGKUFZYSPBMAY-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  cis-3,4-Epoxycyclohexanecarboxylic acid methyl ester 在 sodium azide 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以92%的产率得到methyl c-4-azido-t-3-hydroxy-r-1-cyclohexanecarboxylate
  参考文献：
  名称：

  c-4-Amino-t-3-hydroxy-r-1-cyclohexanecarboxylic acid and cis-4-amino-3-oxo-1-cyclohexanecarboxylic acid—mimetics of dipeptides with a twisted cis-amide bond

  摘要：

  The stereoselective synthesis of the title compounds has been performed. The relative configuration of methyl c-4-(tert-butoxycarbonylamino)-t-3-hydroxy 1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods and its conformation in solution analyzed by NMR. The peptides containing this compound were synthesized and resolved into pure diastereoisomeric forms. Their absolute configuration was determined by independent stereospecific synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00534-0
• 作为产物：
  描述：

  3,4-环氧环己烷羧酸甲酯 在 sodium hydroxide 、 氢溴酸 作用下， 以 异丙醇 为溶剂， 反应 0.42h， 生成 cis-3,4-Epoxycyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  c-4-Amino-t-3-hydroxy-r-1-cyclohexanecarboxylic acid and cis-4-amino-3-oxo-1-cyclohexanecarboxylic acid—mimetics of dipeptides with a twisted cis-amide bond

  摘要：

  The stereoselective synthesis of the title compounds has been performed. The relative configuration of methyl c-4-(tert-butoxycarbonylamino)-t-3-hydroxy 1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods and its conformation in solution analyzed by NMR. The peptides containing this compound were synthesized and resolved into pure diastereoisomeric forms. Their absolute configuration was determined by independent stereospecific synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00534-0

文献信息

• Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ,δ- and β,γ- unsaturated carboxylic acids with an iron porphyrin–iodosylbenzene system
  作者：Masakatsu Komuro、Tsunehiko Higuchi、Masaaki Hirobe

  DOI：10.1039/p19960002309

  日期：——

  The oxidative hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids by a chemical cytochrome P-450 model and rat liver microsomal systems has been investigated. In the chemical system using meso-tetrakis(2,6-dichlorphenyl)porphyrin iron chloride [Fe(TDCIPP)Cl] with iodosylbenzene (PhIO), γ,δ-unsaturated carboxylic acids have been converted into δ-hydroxy-γ-lactones in high yield and with

  研究了化学细胞色素P-450模型和大鼠肝微粒体系统对γ，δ-和β，γ-不饱和羧酸的氧化羟基活化作用。在使用内消旋-四（2,6-二氯苯基）卟啉氯化铁[Fe（TDCIPP）Cl]和碘代苯（PhIO）的化学体系中，γ，δ-不饱和羧酸已转化为δ-羟基-γ-内酯高收率和高立体选择性。作为β，γ-不饱和羧酸的实例，吲哚美辛已被转化为相应的β-羟基γ-内酯。针对内酯化机理的一些实验排除了通过环氧中间体。该产品已用作鉴定微粒体氧化中代谢物的标准品。在消炎痛的情况下，γ-内酯形式在大鼠肝微粒体系统中被检测为代谢产物，产率为1.33％。在2-二乙基氨基乙基-2,2-二戊酸戊酯盐酸盐（SKF-525A）存在下和在混合的CO-O 2（4：1）气氛下，收率显着降低。因此，这些代谢产物被认为是由细胞色素P-450依赖性反应形成的。
• Hexafluoroacetone in Hexafluoro-2-propanol: A Highly Active Medium for Epoxidation with Aqueous Hydrogen Peroxide
  作者：Michiel C. A. van Vliet、Isabel W. C. E. Arends、Roger A. Sheldon

  DOI：10.1055/s-2001-16037

  日期：——

  The combination of hexafluoro-2-propanol and catalytic amounts of hexafluoroacetone gives a versatile medium for epoxidation of a wide range of alkenes with aqueous hydrogen peroxide.

  将六氟-2-丙醇和催化剂量的六氟丙酮结合在一起，可提供一种多功能介质，用于多种烯烃与过氧化氢水溶液的环氧化反应。
• NITROOXY CYCLOALKANE DERIVATIVES
  申请人：Ali Amjad

  公开号：US20110230532A1

  公开（公告）日：2011-09-22

  A compound having the structure wherein Y is selected from the group consisting of —C(O)OR 2 , —C(O)NHR 8 , —C(CH 2 ) 1-2 OR3, OH, and or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.

  一种具有以下结构的化合物，其中Y是从以下群组中选择的：—C(O)OR2、—C(O)NHR8、—C(CH2)1-2OR3、OH，或其药学上可接受的盐，以及使用该化合物治疗高血压的方法。
• ——
  作者：S. I. Okovityi、R. G. Gaponova、Yu. A. Seredyuk、L. I. Kas'yan

  DOI：10.1023/a:1015541012034

  日期：——

  Epoxidation of 1-substituted 3-cyclohexenes was investigated. The stereoisomeric composition of the forming epoxides mixture was established by means of GLC and H-1 NMR spectroscopy, The spectral parameters of the epoxides are considered. The thermodynamical stability of cis- and trans-epoxides was evaluated by molecular mechanics method. For the epoxidation of 1-substituted 3-cyclohexenes with peracetic acid a quantum-chemical calculation of the potential energy surface by PM3 method was carried out.
• Zaitseva; Narizhnaya, Russian Journal of Organic Chemistry, 1996, vol. 32, # 4, p. 480 - 485
  作者：Zaitseva、Narizhnaya

  DOI：——

  日期：——