(S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-5-phenyl-pent-4-enoyl)-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-5-phenyl-pent-4-enoyl)-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(E,2S,3R)-3-hydroxy-2-methyl-5-phenylpent-4-enoyl]-1,3-oxazolidin-2-one
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: XZMLREAGKVFYNG-UMPIWKTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-5-phenyl-pent-4-enoyl)-oxazolidin-2-one 在 lead(II) chloride 、 偶氮二甲酸二乙酯 lithium hydroxide 、 四甲基乙二胺 、 水 、 双氧水 、 四氯化钛 、 N,N-二异丙基乙胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 tert-butyl-[(1E,3R,4S,5Z)-5-ethoxy-4-methyl-1-phenylhepta-1,5-dien-3-yl]oxy-dimethylsilane
  参考文献：
  名称：

  无环烯醇醚的阴离子氧化-Cope重排中意外的立体选择性

  摘要：

  （1 E，5 Z）-4-甲基-5-烷氧基-1-苯基-1,5-庚二烯-3-醇衍生的醇盐的阴离子氧-Cope重排通过含氧阴离子的椅子状过渡态进行即使在甲基和氧阴离子之间存在3,4-顺式关系，因此两个基团在[3,3]-σ重排的过渡态中也都是轴向的。我们认为，这是AOC重排中螯合控制的第一个例子。该反应形成了包含四个手性中心的β-羟基环己酮的立体选择性合成的基础。

  DOI：

  10.1016/s0040-4039(99)02121-8
• 作为产物：
  描述：

  (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-5-phenyl-pent-4-enoyl)-oxazolidin-2-one
  参考文献：
  名称：

  Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis

  摘要：

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.080

文献信息

• EVANS, DAVID A.;BENDER, STEVEN L.;MORRIS, JOEL, J. AMER. CHEM. SOC., 110,(1988) N 8, 2506-2526
  作者：EVANS, DAVID A.、BENDER, STEVEN L.、MORRIS, JOEL

  DOI：——

  日期：——
• Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.tet.2011.01.080

  日期：2011.3

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.
• Unexpected stereoselectivity in the anionic oxy-Cope rearrangement of acyclic enol ethers
  作者：Alistair P Rutherford、Richard C Hartley

  DOI：10.1016/s0040-4039(99)02121-8

  日期：2000.1

  The anionic oxy-Cope rearrangement of alkoxides derived from (1E,5Z)-4-methyl-5-alkoxy-1-phenyl-1,5-heptadien-3-ols proceeds via a chair-like transition state with the oxyanion axial, even when there is a 3,4-syn-relationship between the methyl group and the oxyanion so that both groups are axial in the transition state of the [3,3]-sigmatropic rearrangement. We believe that this is the first example

  （1 E，5 Z）-4-甲基-5-烷氧基-1-苯基-1,5-庚二烯-3-醇衍生的醇盐的阴离子氧-Cope重排通过含氧阴离子的椅子状过渡态进行即使在甲基和氧阴离子之间存在3,4-顺式关系，因此两个基团在[3,3]-σ重排的过渡态中也都是轴向的。我们认为，这是AOC重排中螯合控制的第一个例子。该反应形成了包含四个手性中心的β-羟基环己酮的立体选择性合成的基础。