(3S,4R)-3,4-dihydroxy-6-phenyl-5-en-2-hexanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (3S,4R)-3,4-dihydroxy-6-phenyl-5-en-2-hexanone
• 英文别名: (3S,4R,E)-3,4-dihydroxy-6-phenylhex-5-en-2-one；(E,3S,4R)-3,4-dihydroxy-6-phenylhex-5-en-2-one
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: FXZNASZOJZXZHM-IDDPWSFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E,E)-6-phenyl-3,5-hexadien-2-one 在 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 28.0h， 以60.6%的产率得到(5R,6R)-5,6-dihydroxy-6-phenyl-3-en-2-hexanone
  参考文献：
  名称：

  Remote steric effect on the regioselectivity of Sharpless asymmetric dihydroxylation

  摘要：

  Studies on the regioselectivities for the Sharpless asymmetric dillydroxylation (AD) of conjugated dienoates, trienoates, dienones and dienamides are described. Excellent regioselectivities were obtained in straight chain dienoates, all trienoates, ketones damicles. The remote branched iso-propyl and tert-butyl groups of dienoates greatly lowered the normally excellent regiocontrol. This observation is rationalized in terms of substrate conformational changes, and the steric interaction between the branched methyl group of iso-propyl ortertbutyl groups and the ethyl group Oil the (DHQD)(2)PHAL ligand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.119

文献信息

• Engineering of <scp>d</scp>-fructose-6-phosphate aldolase A for improved activity towards cinnamaldehyde
  作者：Xiaohong Yang、Lidan Ye、Aipeng Li、Chengcheng Yang、Huilei Yu、Jiali Gu、Fei Guo、Ling Jiang、Fan Wang、Hongwei Yu

  DOI：10.1039/c6cy01622g

  日期：——

  d-Fructose-6-phosphate aldolase A (FSAA) from Escherichia coli was engineered for enhanced catalytic efficiency towards cinnamaldehyde.

  d-果糖-6-磷酸醛酸酶A（FSAA）来自大肠杆菌，经过工程改造以提高对肉桂醛的催化效率。
• A Catalytic Aldol Reaction and Condensation through In Situ Boron “Ate” Complex Enolate Generation in Water
  作者：Karel Aelvoet、Andrei S. Batsanov、Alexandrea J. Blatch、Christophe Grosjean、Leonard G. F. Patrick、Christian A. Smethurst、Andrew Whiting

  DOI：10.1002/anie.200704293

  日期：2008.1.11
• Remote steric effect on the regioselectivity of Sharpless asymmetric dihydroxylation
  作者：Yan Zhang、George A. O'Doherty

  DOI：10.1016/j.tet.2005.03.119

  日期：2005.6

  Studies on the regioselectivities for the Sharpless asymmetric dillydroxylation (AD) of conjugated dienoates, trienoates, dienones and dienamides are described. Excellent regioselectivities were obtained in straight chain dienoates, all trienoates, ketones damicles. The remote branched iso-propyl and tert-butyl groups of dienoates greatly lowered the normally excellent regiocontrol. This observation is rationalized in terms of substrate conformational changes, and the steric interaction between the branched methyl group of iso-propyl ortertbutyl groups and the ethyl group Oil the (DHQD)(2)PHAL ligand. (c) 2005 Elsevier Ltd. All rights reserved.