(Z)-2-bromovinyl octanoate | 459456-65-6

• 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: (Z)-2-bromovinyl octanoate
• 英文别名: [(Z)-2-bromoethenyl] octanoate
• CAS: 459456-65-6
• 化学式: C₁₀H₁₇BrO₂
• 分子量: 249.148
• InChiKey: ZBIVJNJMPLCVRK-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  E-庚烯-1-基硼酸 、 (Z)-2-bromovinyl octanoate 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以86%的产率得到Octanoic acid (1Z,3E)-nona-1,3-dienyl ester
  参考文献：
  名称：

  A Novel Method for the Construction of (Z,E)- or (Z,Z)-Conjugated Alkadienyl Carboxylates

  摘要：

  [GRAPHICS]The stereocontrolled dehydrobromination of 1,2-dibromoethyl carboxylates giving (Z)-2-bromovinyl carboxylates could readily be approached by using DBU and a catalytic amount of hydroquinone as a base at -78 degreesC. The first investigation on the Suzuki-type cross-coupling of (2)-2-bromovinyl carboxylates as electrophiles with stereodefined alkenylboronic acids provides a novel method for the construction of (Z,E)or (Z,Z)-conjugated alkadienyl carboxylate moieties, which are often present in a range of natural products.

  DOI：

  10.1021/ol026286p
• 作为产物：
  描述：

  1,2-dibromoethyl octanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(Z)-2-bromovinyl octanoate
  参考文献：
  名称：

  A Novel Method for the Construction of (Z,E)- or (Z,Z)-Conjugated Alkadienyl Carboxylates

  摘要：

  [GRAPHICS]The stereocontrolled dehydrobromination of 1,2-dibromoethyl carboxylates giving (Z)-2-bromovinyl carboxylates could readily be approached by using DBU and a catalytic amount of hydroquinone as a base at -78 degreesC. The first investigation on the Suzuki-type cross-coupling of (2)-2-bromovinyl carboxylates as electrophiles with stereodefined alkenylboronic acids provides a novel method for the construction of (Z,E)or (Z,Z)-conjugated alkadienyl carboxylate moieties, which are often present in a range of natural products.

  DOI：

  10.1021/ol026286p