t-butyl (R)-2-methylbut-3-enoate | 528846-35-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: t-butyl (R)-2-methylbut-3-enoate
• 英文别名: tert-butyl (2R)-2-methylbut-3-enoate
• CAS: 528846-35-7
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: CFECSJGONLRCJC-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  t-butyl (R)-2-methylbut-3-enoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (R)-2-methyl-3-buten-1-ol
  参考文献：
  名称：

  Enantioselective Synthesis of α-Alkyl-β,γ-unsaturated Esters through Efficient Cu-Catalyzed Allylic Alkylations

  摘要：

  A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.

  DOI：

  10.1021/ja0300618
• 作为产物：
  描述：

  Dimethylzinc 、 diethyl (E)-3-(tert-butoxycarbonyl)-2-propen-1-yl phosphate 在 copper(I) trifluoromethanesulfonate benzene 、 2-hydroxy-1-naphthylidene-Cha-Nle-NHnBu 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 t-butyl (R)-2-methylbut-3-enoate 、 t-butyl (S)-2-methylbut-3-enoate
  参考文献：
  名称：

  Enantioselective Synthesis of α-Alkyl-β,γ-unsaturated Esters through Efficient Cu-Catalyzed Allylic Alkylations

  摘要：

  A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.

  DOI：

  10.1021/ja0300618

文献信息

• Enantioselective Synthesis of α-Alkyl-β,γ-unsaturated Esters through Efficient Cu-Catalyzed Allylic Alkylations
  作者：Kerry E. Murphy、Amir H. Hoveyda

  DOI：10.1021/ja0300618

  日期：2003.4.1

  A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.