(2S,3R,4E)-(+)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester | 86853-07-8

• 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,3R,4E)-(+)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester
• 英文别名: (2S,3R)-(E)-methyl 3-hydroxy-2-methyl-5-phenylpent-4-enoate；methyl (E,2S,3R)-3-hydroxy-2-methyl-5-phenylpent-4-enoate
• CAS: 86853-07-8
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: BUZBSPGKKVOQOO-SEOINYINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-(+)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 生成 methyl (E)-(3R*,4S*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate
  参考文献：
  名称：

  Meyer, Hartmut H., Liebigs Annalen der Chemie, 1984, # 4, p. 791 - 801

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 2-methyl-3-oxo-5-phenyl-4-pentenoate 以7%的产率得到(2S,3R,4E)-(+)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester
  参考文献：
  名称：

  The absolute configuration of oudemansin total synthesis of (−)-oudemansin

  摘要：

  DOI：

  10.1016/s0040-4039(00)81829-8

文献信息

• Generation of (<i>E</i>)-Silylketene Acetals in a Rhodium-DuPhos Catalyzed Two-Step Reductive Aldol Reaction
  作者：Cun-Xiang Zhao、Jonathan Bass、James P. Morken

  DOI：10.1021/ol016279l

  日期：2001.9.1

  [GRAPHICS]Mechanistic studies employing in situ NMR analysis implicate intermediate silicon enolates as reactive intermediates in the Rh-DuPhos catalyzed two-step reductive aldol reaction with Cl2MeSiH. These enolates undergo noncatalyzed reaction with a variety of aldehydes to give the derived syn-aldol adduct in high yields and diastereoselection.
• Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes
  作者：Arun K Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(02)01113-9

  日期：2002.8

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates
  作者：P. Veeraraghavan Ramachandran、Debarshi Pratihar

  DOI：10.1021/ol802850w

  日期：2009.4.2

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.
• The chemistry of enoxysilacyclobutanes: highly selective, uncatalyzed aldol additions
  作者：Scott E. Denmark、Brian D. Griedel、Diane M. Coe

  DOI：10.1021/jo00057a002

  日期：1993.2

  O-(Silacyclobutyl)ketene acetals derived from esters, thiol esters, and amides reacted with a variety of aldehydes at room temperature without the need for catalysts. The O,O-ketene acetal of E-configuration reacted rapidly to afford the syn aldol products with high diastereoselectivity (93/7-99/1).
• The absolute configuration of oudemansin total synthesis of (−)-oudemansin
  作者：Hiroyuki Akita、Hiroko Koshiji、Akiya Furuichi、Koki Horikoshi、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)81829-8

  日期：1983.1