(S)-oct-7-ene-1,2-diol

• 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: (S)-oct-7-ene-1,2-diol
• 英文别名: (2S)-oct-7-ene-1,2-diol
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: UXGHWJFURBQKCJ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,7-辛二烯 在 AD-mix-β 作用下， 生成 (S)-oct-7-ene-1,2-diol 、 (2R)-oct-7-en-1,2-diol
  参考文献：
  名称：

  有效和通用的4-羟基化的无水产乙酸原素的丁烯内酯亚基的合成

  摘要：

  已经通过有效且通用的途径合成了标题丁烯内酯2，该途径通过使用前体3-丁炔-2-醇和末端环氧化物的各个对映异构体提供了与任何立体异构体的接触。

  DOI：

  10.1016/s0040-4039(00)78332-8

文献信息

• Structure-Guided Regulation in the Enantioselectivity of an Epoxide Hydrolase to Produce Enantiomeric Monosubstituted Epoxides and Vicinal Diols via Kinetic Resolution
  作者：Die Hu、Bo-Chun Hu、Xiao-Dong Hou、Dong Zhang、Yu-Qing Lei、Yi-Jian Rao、Min-Chen Wu

  DOI：10.1021/acs.orglett.1c04348

  日期：2022.3.11

  Structure-guided microtuning of an Aspergillus usamii epoxide hydrolase was executed. One mutant, A214C/A250I, displayed a 12.6-fold enhanced enantiomeric ratio (E = 202) toward rac-styrene oxide, achieving its nearly perfect kinetic resolution at 0.8 M in pure water or 1.6 M in n-hexanol/water. Several other beneficial mutants also displayed significantly improved E values, offering promising biocatalysts

  对Aspergillus usamii环氧水解酶进行了结构引导的微调。一种突变体 A214C/A250I对消旋-氧化苯乙烯的对映体比 ( E = 202)提高了 12.6 倍，在纯水中 0.8 M 或正己醇/水中 1.6 M 时实现了近乎完美的动力学分辨率。其他一些有益的突变体也显示出显着提高的E值，为获得 19 种结构多样的手性单取代环氧化物（97.1 – ≥ 99% ee s）和邻二醇（56.2–98.0% ee p）提供了有希望的生物催化剂，并且产率很高。
• “Cassette” In Situ Enzymatic Screening Identifies Complementary Chiral Scaffolds for Hydrolytic Kinetic Resolution Across a Range of Epoxides
  作者：Sangeeta Dey、Douglas R. Powell、Chunhua Hu、David B. Berkowitz

  DOI：10.1002/anie.200701280

  日期：2007.9.17

  ‘Cassette’-ISES (In Situ Enzymatic Screening) Identifies Complementary Chiral Scaffolds for Hydrolytic Kinetic Resolution Across a Range of Epoxides A new ‘Cassette’-In Situ Enzymatic Screen (ISES) for combinatorial catalysis is introduced. This allows the experimentalist to obtain an information-rich readout, in real time, providing an estimate of the sense and magnitude of enantioselectivity across more than one substrate. In its first iteration, the screen identified CoIII-salen catalysts with β-pinene- and α-naphthylalanine-derived chiral scaffolds with broad, yet complementary, substrate specificities.
• Enantioselectivities of yeast epoxide hydrolases for 1,2-epoxides
  作者：Adriana L. Botes、Carel A.G.M. Weijers、Piet J. Botes、Martie S. van Dyk

  DOI：10.1016/s0957-4166(99)00355-9

  日期：1999.8

  Kinetic resolution of homologous series of unbranched 1,2-epoxyalkanes (C-4 to C-12), 1,2-epoxyalkenes (C-4, C-6 and C-8), a 2,2-dialkylsubstituted epoxide (2-methyl-1,2-epoxyheptane) and a benzyloxy-substituted epoxide (benzyl glycidyl ether) was investigated using resting cells of 10 different yeast strains. Biocatalysts with excellent enantioselectivity (E>100) and high initial reaction rates (>300 nmol/min/mg dry weight) were found for the 2-monosubstituted aliphatic epoxides C-6 to C-8. Yeast strains belonging to the genera Rhodotorula, Rhodosporidium and Trichosporon all preferentially hydrolyzed (R)-1,2-epoxides with retention of configuration. The epoxide hydrolases of all the yeast strains are membrane-associated. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An efficient and versatile synthesis of the butenolide subunit of 4-hydroxylated annonaceous acetogenins
  作者：Thomas R. Hoye、Paul E. Humpal、Jorge I. Jiménez、Michael J. Mayer、Lushi Tan、Zhixiong Ye

  DOI：10.1016/s0040-4039(00)78332-8

  日期：1994.10

  Title butenolides 2 have been synthesized by an efficient and versatile route that provides access to any stereoisomer by use of individual enantiomers of the precursors 3-butyn-2-ol and terminal epoxides.

  已经通过有效且通用的途径合成了标题丁烯内酯2，该途径通过使用前体3-丁炔-2-醇和末端环氧化物的各个对映异构体提供了与任何立体异构体的接触。