(2S,3S,E)-5-苯基戊-4-烯-2,3-二醇 | 66820-55-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 中文名称: (2S,3S,E)-5-苯基戊-4-烯-2,3-二醇
• 英文名称: (E)-5-phenylpent-4-ene-2,3-diol
• CAS: 66820-55-1；67470-74-0；70095-23-7；91177-70-7；100679-75-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: GLNQFDQDPXHTRK-BQYQJAHWSA-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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,E)-5-苯基戊-4-烯-2,3-二醇 生成 [(E)-3-acetyloxy-5-phenylpent-4-en-2-yl] acetate
  参考文献：
  名称：

  FUGANTI C.; GRASSELLI P., CHEM. AND IND., 1977, NO 24, 983

  摘要：

  DOI：
• 作为产物：
  描述：

  Acetic acid (E)-(S)-1-methyl-2-oxo-4-phenyl-but-3-enyl ester 在 四丁基氟化铵 二甲基苯基硅烷 作用下， 生成 (2S,3S,E)-5-苯基戊-4-烯-2,3-二醇
  参考文献：
  名称：

  Synthesis of 1-substituted (S)-4-acetoxy-1-penten-3-ones using (S)-lactic acid as a chiral source and their synthetic reactions

  摘要：

  DOI：

  10.1016/s0040-4039(01)91269-9

文献信息

• Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes
  作者：Won Jun Jang、Jaesook Yun

  DOI：10.1002/anie.201806937

  日期：2018.9.10

  report the copper‐catalyzed stereoselective addition of in situ generated chiral boron‐α‐alkyl intermediates to various aldehydes including α,β‐unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2‐hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo‐ and enantioselectivity up to a ratio

  我们报道了在温和条件下，铜催化的立体选择性地将原位生成的手性硼-α-烷基中间体添加到各种醛中，包括α，β-不饱和醛。这种串联和多组分方法促进了具有连续立体中心的对映异构体富集的1,2-羟基硼酸酯的合成，收率高，非对映异构体和对映异构体的选择性高达98：2。特别是，α，β-不饱和醛通过1,2-加成成功地用作Cu-H催化中的亲电子试剂，而没有明显的还原反应。所得的1,2-羟基硼酸酯用于各种转化中。
• Extractive biocatalysis: A powerful tool in selectivity control in yeast biotransformations
  作者：Paola D'Arrigo、Claudio Fuganti、Giuseppe Pedrocchi Fantoni、Stefano Servi

  DOI：10.1016/s0040-4020(98)00941-7

  日期：1998.12

  The effect of absorbing resins on the yeast reduction of cl,P-unsaturated carbonyl compounds is reported. Enantioselectivity, chemoselectivity and space-time yields of the biotransformation are impressively enhanced. The distribution of substrates and products between the resin and the water phase shows that the improved selectivity has to be attributed to the control of substrate concentration, (C) 1998 Elsevier Science Ltd. All rights reserved.
• Highly diastereocontrolled reduction of ketones by means of hydrosilanes. Practical synthesis of optically active 1,2-diols and 2-amino alcohols of threo or erythro configuration
  作者：Makoto Fujita、Tamejiro Hiyama

  DOI：10.1021/ja00328a062

  日期：1984.8
• Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes
  作者：Matthew V. Joannou、Brandon S. Moyer、Simon J. Meek

  DOI：10.1021/jacs.5b03477

  日期：2015.5.20

  The first catalytic enantio- and diastereoselective synthesis of 1;2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., arid 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the alpha-boryl component.
• FUJITA, MAKOTO;HIYAMA, TAMEJIRO, J. AMER. CHEM. SOC., 1984, 106, N 16, 4629-4630
  作者：FUJITA, MAKOTO、HIYAMA, TAMEJIRO

  DOI：——

  日期：——