rac-(E)-2-<(tert-butyl)dimethylsilyl>-1-phenylpent-3-en-2-ol | 228575-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-(E)-2-<(tert-butyl)dimethylsilyl>-1-phenylpent-3-en-2-ol
• 英文别名: (E)-2-[tert-butyl(dimethyl)silyl]-1-phenylpent-3-en-2-ol
• CAS: 228575-57-3
• 化学式: C₁₇H₂₈OSi
• 分子量: 276.494
• InChiKey: UXNKXBHNBALXEN-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  rac-(E)-2-<(tert-butyl)dimethylsilyl>-1-phenylpent-3-en-2-ol 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(R*,R*)-3-<(tert-butyl)dimethylsilyl>-4-hydroxy-1-phenylpentan-2-one
  参考文献：
  名称：

  A Novel Stereoselective Reaction Cascade Leading fromα-Silylated Allylic Alcohols to Aldol-Type Products

  摘要：

  The treatment of alpha-silylated allylic alcohols with epoxidizing reagents afforded in a highly stereocontrolled fashion a-silylated aldols. The transformation is proposed to proceed either by a reaction cascade involving stereospecific epoxidation of the allylic-alcohol moiety followed by an acid-supported pinacol-type rearrangement, or by a sequence consisting of a pi-face-selective electrophilic attack at the allylic silane moiety with hyperconjugative stabilization of the evolving carbocation, followed by rearrangement of the thus obtained pentacoordinated silanium ion (see Scheme 3). Depending on the reaction conditions, the pi-face selectivity of the oxidation step is controlled by the: stereogenic C-atom or the more remote Si-center of chirality.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<561::aid-hlca561>3.0.co;2-u
• 作为产物：
  描述：

  2-benzyl-1,3-dithiane 在 正丁基锂 、 lithium (1 percent sodium) 、 1,2-二溴乙烷 、 mercury dichloride 、 cadmium(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 、 丙酮 、 甲苯 、 正戊烷 为溶剂， 反应 27.0h， 生成 rac-(E)-2-<(tert-butyl)dimethylsilyl>-1-phenylpent-3-en-2-ol
  参考文献：
  名称：

  A Novel Stereoselective Reaction Cascade Leading fromα-Silylated Allylic Alcohols to Aldol-Type Products

  摘要：

  The treatment of alpha-silylated allylic alcohols with epoxidizing reagents afforded in a highly stereocontrolled fashion a-silylated aldols. The transformation is proposed to proceed either by a reaction cascade involving stereospecific epoxidation of the allylic-alcohol moiety followed by an acid-supported pinacol-type rearrangement, or by a sequence consisting of a pi-face-selective electrophilic attack at the allylic silane moiety with hyperconjugative stabilization of the evolving carbocation, followed by rearrangement of the thus obtained pentacoordinated silanium ion (see Scheme 3). Depending on the reaction conditions, the pi-face selectivity of the oxidation step is controlled by the: stereogenic C-atom or the more remote Si-center of chirality.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<561::aid-hlca561>3.0.co;2-u

文献信息

• A Novel Stereoselective Reaction Cascade Leading fromα-Silylated Allylic Alcohols to Aldol-Type Products
  作者：Jürg Fässler、Valentin Enev、Stefan Bienz

  DOI：10.1002/(sici)1522-2675(19990407)82:4<561::aid-hlca561>3.0.co;2-u

  日期：1999.4.7

  The treatment of alpha-silylated allylic alcohols with epoxidizing reagents afforded in a highly stereocontrolled fashion a-silylated aldols. The transformation is proposed to proceed either by a reaction cascade involving stereospecific epoxidation of the allylic-alcohol moiety followed by an acid-supported pinacol-type rearrangement, or by a sequence consisting of a pi-face-selective electrophilic attack at the allylic silane moiety with hyperconjugative stabilization of the evolving carbocation, followed by rearrangement of the thus obtained pentacoordinated silanium ion (see Scheme 3). Depending on the reaction conditions, the pi-face selectivity of the oxidation step is controlled by the: stereogenic C-atom or the more remote Si-center of chirality.