(1SR,2RS,4SR,5RS)-6-Oxabicyclo<3.1.0>hexane-2,4-diol | 138513-65-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (1SR,2RS,4SR,5RS)-6-Oxabicyclo<3.1.0>hexane-2,4-diol
• 英文别名: trans-1,4-dihydroxycyclopentene oxide；(1R,2S,4R,5S)-6-oxabicyclo[3.1.0]hexane-2,4-diol
• CAS: 138513-65-2
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: RQUGIRLRZUJKJU-YPVPKEFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1SR,2RS,4SR,5RS)-6-Oxabicyclo<3.1.0>hexane-2,4-diol 在 吡啶 、 sodium dihydrogenphosphate 、 sodium azide 、 Electrophorus electricus acetylcholinesterase 作用下， 反应 24.0h， 生成 (1S,2S,4R,5S)-(-)-4-hydroxy-6-oxabicyclo<3.1.0>hex-2-yl acetate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 在 甲醇 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 77.08h， 生成 (1SR,2RS,4SR,5RS)-6-Oxabicyclo<3.1.0>hexane-2,4-diol
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0

文献信息

• Stereoselective Synthetic Approaches to Highly Substituted Cyclopentanes via Electrophilic Additions to Mono-, Di-, and Trisubstituted Cyclopentenes
  作者：Matthew A. Clark、Bradley K. Goering、Jun Li、Bruce Ganem

  DOI：10.1021/jo000101f

  日期：2000.6.1

  attracted considerable interest. However, the effect of allylic and homoallylic substituents in cyclopentenyl systems has not been investigated systematically. Studies on a series of mono, di-, and trisubstituted cyclopentenes are reported in which trans-vicinal-additions favor a syn-selective approach of electrophiles to the cyclopentene system. The formal addition of HOBr, HOCl, CH(3)SCl, and dim

  烯丙基取代的烯烃的亲电子加成具有广泛的合成用途。在这种反应中控制立体选择性引起了极大的兴趣。然而，尚未系统地研究烯丙基和均烯丙基取代基在环戊烯基体系中的作用。据报道，对一系列单，二和三取代的环戊烯进行了研究，其中反式-邻位加成有利于亲电体对环戊烯系统的同选择方法。已经进行了HOBr，HOCl，CH（3）SCl和四氟硼酸二甲基（甲硫基）s（DMTSF）/ NaN（3）与各种环戊烯底物的正式添加，并且各种烯丙基取代基对这些选择性的影响已经检查过了。HOBr，HOCl，和DMTSF对高度官能化的底物的合成具有可预见的选择性，主要或专门提供一种产品。甲烷亚甲酰氯的添加很难预测，但可以通过适当改变溶剂和底物来调节。已证明结果可用于（+）-Trehazolin和（+）-Allosamidin的总合成。
• Lipase-catalyzed transesterification of meso-cyclopentane diols
  作者：Fritz Theil、Hans Schick、Gabriele Winter、Günter Reck

  DOI：10.1016/s0040-4020(01)88281-8

  日期：1991.9

  The lipase-catalyzed transesterification of the meso-cyclopentane diols 1a - 6a with vinyl acetate in tetrahydrofuran/triethylamine in the presence of lipases of different origin has been investigated. Depending on the structure of the substrate and the origin of the lipase chiral cyclopentane derivatives with high enantiomeric excess could be obtained in good to excellent chemical yields.