(2S,3S)-5-phenyl-4-pentene-2,3-diol | 91177-70-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2S,3S)-5-phenyl-4-pentene-2,3-diol
• 英文别名: (E,2S,3S)-5-phenylpent-4-ene-2,3-diol
• CAS: 91177-70-7
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: GLNQFDQDPXHTRK-QARYBLBWSA-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)-5-phenyl-4-pentene-2,3-diol 、 环己酮二甲缩酮 生成 (3S,4S,1E)-3,4-(cyclohexylidenedioxy)-1-phenyl-1-pentene
  参考文献：
  名称：

  FUJITA, MAKOTO;HIYAMA, TAMEJIRO, J. ORG. CHEM., 53,(1988) N3, C. 5405-5415

  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)-5-phenyl-4-pentene-2,3-diol
  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

• Selective asymmetric dihydroxylation of polyenes
  作者：Heinrich Becker、Marcos A. Soler、K. Barry Sharpless

  DOI：10.1016/0040-4020(94)01021-q

  日期：1995.1

  The asymmetric dihydroxylation procedure (AD) is applied to a variety of polyenes. In many cases excellent regioselectivities are obtained. The observed selectivities are rationalized in terms of electronic and/or steric effects inherent to the substrate, superimposed on the substrate's favorable or unfavorable interactions with the binding pocket of the AD ligand. Surprisingly, for medium and large

  不对称二羟基化方法（AD）适用于多种多烯。在许多情况下，可获得极好的区域选择性。观察到的选择性根据底物固有的电子和/或空间效应合理化，并叠加在底物与AD配体的结合口袋的有利或不利相互作用上。令人惊讶地，对于具有反式-双键的中型和大型环烯烃，使用嘧啶配体实现了优异的对映选择性。由所有反式环十二碳三烯制备具有D 3对称性的六元醇。
• 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。
• Fluoride ion-catalyzed reduction of aldehydes and ketones with hydrosilanes. Synthetic and mechanistic aspects and an application to the threo-directed reduction of .alpha.-substituted alkanones
  作者：Makoto Fujita、Tamejiro Hiyama

  DOI：10.1021/jo00258a003

  日期：1988.11
• 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.
• On the steric course of bakers' yeast reduction of .alpha.-hydroxy ketones
  作者：Claudio Fuganti、Piero Grasselli、Stefano Servi、Franca Spreafico、Carlo Zirotti、Paolo Casati

  DOI：10.1021/jo00195a051

  日期：1984.10