(S,E)-4-(6-oxo-1,3,5-dioxazepan-5-yl)but-2-enyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate | 881852-17-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,E)-4-(6-oxo-1,3,5-dioxazepan-5-yl)but-2-enyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate
• 英文别名: [(E)-4-(3-oxo-1,9-dioxa-4-azacycloheptadec-4-yl)but-2-enyl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 881852-17-1
• 化学式: C₃₂H₅₀N₂O₇
• 分子量: 574.758
• InChiKey: KNWUHJYPXCFKIU-QMVUCBSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(but-3-en-1-yl)-1,9-dioxa-4-azacycloheptadecan-3-one 、 BOC-L-苯丙氨酸 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 苯基-P-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以62%的产率得到(S,E)-4-(6-oxo-1,3,5-dioxazepan-5-yl)but-2-enyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation

  摘要：

  A highly general, predictably selective C H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (1 6 examples, EIZ L- 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C H oxidation vs C C bond-forming methods are evaluated and discussed in four "case studies".

  DOI：

  10.1021/ja104826g

文献信息

• Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation
  作者：Nicolaas A. Vermeulen、Jared H. Delcamp、M. Christina White

  DOI：10.1021/ja104826g

  日期：2010.8.18

  A highly general, predictably selective C H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (1 6 examples, EIZ L- 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C H oxidation vs C C bond-forming methods are evaluated and discussed in four "case studies".