2-[(Z)-5-chloro-1-diethoxyphosphorylpent-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 328114-11-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2-[(Z)-5-chloro-1-diethoxyphosphorylpent-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 328114-11-0
• 化学式: C₁₅H₂₉BClO₅P
• 分子量: 366.63
• InChiKey: WHCMUCBZJZYCNJ-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-碘甲苯 、 2-[(Z)-5-chloro-1-diethoxyphosphorylpent-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以60%的产率得到1-[(Z)-5-chloro-1-diethoxyphosphorylpent-1-enyl]-4-methylbenzene
  参考文献：
  名称：

  Control of hydroboration of 1-alkynylphosphonates, followed by Suzuki coupling provides regio- and stereospecific synthesis of di-substituted 1-alkenylphosphonates

  摘要：

  Hydroboration of 1-alkynylphosphonates can be controlled to place boron on either C1 or C2 of the triple bond by control of reaction conditions. Initial hydroboration occurs on C1 (kinetic product), which can be isomerized to place boron on C2 (thermodynamic product) by extended heating or by use of large amounts of catalyst. Suzuki reaction of the hydroboration products with aryliodides provides a regio- and stereospecific route to disubstituted vinylphosphonates (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01696-3
• 作为产物：
  描述：

  频那醇硼烷 、 diethyl (5-chloropent-1-yn-1-yl)phosphonate 以 二氯甲烷 为溶剂， 生成 2-[(Z)-5-chloro-1-diethoxyphosphorylpent-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Control of hydroboration of 1-alkynylphosphonates, followed by Suzuki coupling provides regio- and stereospecific synthesis of di-substituted 1-alkenylphosphonates

  摘要：

  Hydroboration of 1-alkynylphosphonates can be controlled to place boron on either C1 or C2 of the triple bond by control of reaction conditions. Initial hydroboration occurs on C1 (kinetic product), which can be isomerized to place boron on C2 (thermodynamic product) by extended heating or by use of large amounts of catalyst. Suzuki reaction of the hydroboration products with aryliodides provides a regio- and stereospecific route to disubstituted vinylphosphonates (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01696-3