(3R,4R)-1-methoxy-3,4-nonanediol | 204987-22-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R)-1-methoxy-3,4-nonanediol
• 英文别名: (3R,4R)-1-methoxynonane-3,4-diol
• CAS: 204987-22-4
• 化学式: C₁₀H₂₂O₃
• 分子量: 190.283
• InChiKey: CHUBNBZQQWEUCO-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-methoxy-3,4-nonanediol 、 碘甲烷 在 sodium hydride 作用下， 生成 (+)-1,3,4-trimethoxynonane
  参考文献：
  名称：

  Deracemization of (±)-cis-dialkyl substituted oxides via enantioconvergent hydrolysis catalysed by microsomal epoxide hydrolase

  摘要：

  Both enantiomers of cis-(+/-)-2,3-epoxyheptane 1a, cis-3,4-epoxyheptane 1b, cis-3,4-epoxynonane 1c, cis-3,4-epoxynonane-1-ol Id, and cis-1-methoxy-3,4-epoxynonane le undergo a highly stereoselective microsomal epoxide hydrolase catalysed hydration at the (S) carbon to give the corresponding three (R,R)-diol at complete conversion. A total kinetic resolution of racemic epoxides is also obtained with la and 1e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00630-7
• 作为产物：
  描述：

  (Z)-1-methoxy-3-nonene (Z)-3-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-nonenyl acetate 在 potassium fluoride 、 microsomal epoxide hydrolase from rabbit liver 、 水 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3R,4R)-1-methoxy-3,4-nonanediol
  参考文献：
  名称：

  Deracemization of (±)-cis-dialkyl substituted oxides via enantioconvergent hydrolysis catalysed by microsomal epoxide hydrolase

  摘要：

  Both enantiomers of cis-(+/-)-2,3-epoxyheptane 1a, cis-3,4-epoxyheptane 1b, cis-3,4-epoxynonane 1c, cis-3,4-epoxynonane-1-ol Id, and cis-1-methoxy-3,4-epoxynonane le undergo a highly stereoselective microsomal epoxide hydrolase catalysed hydration at the (S) carbon to give the corresponding three (R,R)-diol at complete conversion. A total kinetic resolution of racemic epoxides is also obtained with la and 1e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00630-7

文献信息

• Stereo- and enantioselectivity of the soluble epoxide hydrolase-catalysed hydrolysis of (±)-cis-dialkyl substituted oxiranes
  作者：Cinzia Chiappe、Consiglia Doriana Palese

  DOI：10.1016/s0040-4020(99)00657-2

  日期：1999.9

  into the corresponding threo-diols 2a-e by soluble epoxide hydrolase catalysed hydrolysis. The reaction proceeds with a substrate and product enantioselection, which is highly dependent on the substituents at the oxirane ring. Whereas the hydrolysis of racemic 1a shows practically no enantioselection, that of its isomer 1b, gives after complete hydrolysis, in a stereoconvergent way, the corresponding threo-diol

  顺式-（±）-2,3-环氧庚烷（1a），顺式-3,4-环氧庚烷（1b），顺式-3,4-环氧壬烷（1c）顺式-3,4-环氧壬烷-1-醇的两种对映体（1d）和顺式-1-甲氧基-3,4-环氧壬烷（1e）通过可溶性环氧化物水解酶催化水解而转化为相应的苏-二醇2a-e。反应以底物和产物对映体进行，该对映体高度依赖于环氧乙烷环上的取代基。而外消旋体1a的水解几乎没有显示出其异构体1b的对映异构，完全水解后，以立体收敛的方式给出了相应的苏-二醇（3R，4R）-2b。另一方面，环氧化物1c-e的水解过程中，相当好的（1c和1e）或完全的（1d）底物对映体进行水解，得到外消旋体（2c）或以立体会聚的方式旋光富集（2e）或纯净的（2d）二醇。从以前用微粒体环氧化物水解酶水解相同底物的结果中观察到了显着差异。
• Deracemization of (±)-cis-dialkyl substituted oxides via enantioconvergent hydrolysis catalysed by microsomal epoxide hydrolase
  作者：Cinzia Chiappe、Antonio Cordoni、Giacomo Lo Moro、Consiglia Doriana Palese

  DOI：10.1016/s0957-4166(97)00630-7

  日期：1998.1

  Both enantiomers of cis-(+/-)-2,3-epoxyheptane 1a, cis-3,4-epoxyheptane 1b, cis-3,4-epoxynonane 1c, cis-3,4-epoxynonane-1-ol Id, and cis-1-methoxy-3,4-epoxynonane le undergo a highly stereoselective microsomal epoxide hydrolase catalysed hydration at the (S) carbon to give the corresponding three (R,R)-diol at complete conversion. A total kinetic resolution of racemic epoxides is also obtained with la and 1e. (C) 1998 Elsevier Science Ltd. All rights reserved.