(1E,6E)-pinacol 7-carboethoxy-1,6-heptadienylboronate | 153742-70-2

• 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: (1E,6E)-pinacol 7-carboethoxy-1,6-heptadienylboronate
• 英文别名: ethyl (2E,7E)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-2,7-dienoate
• CAS: 153742-70-2
• 化学式: C₁₆H₂₇BO₄
• 分子量: 294.199
• InChiKey: JSDRCBIVIJENIL-DCIPZJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1E,6E)-pinacol 7-carboethoxy-1,6-heptadienylboronate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(E)-pinacol 6-butyl-7-carboethoxy-1-heptenylboronate
  参考文献：
  名称：

  Preparation of polyfunctional olefins and allenes using 1,1-bimetallics of zinc and zirconium

  摘要：

  The hydrozirconation of various alkenylzinc halides with Cp2Zr(H)Cl in dry dichloromethane provides 1,1-dimetalloalkanes of zinc and zirconium which react with aldehydes, providing (E)-alkenes with good to excellent stereoselectivity (up to 98% E). The reaction tolerates the presence of a wide range of functionalities in the dimetallic species as well as in the aldehyde, allowing the preparation of functionalized olefins. Ketones can also be olefinated by these reagents. However, only a moderate stereoselectivity is observed. The hydrozirconation of alkynylzinc halides with CP2Zr(H)Cl gives 1,1-dimetalloalkenes of zinc and zirconium which react with aldehydes, affording allenes. The olefination of alpha,beta-unsaturated aldehydes provides a short access of 1,2,4-trienes.

  DOI：

  10.1021/om00013a020
• 作为产物：
  描述：

  pinacol (E)-(5-iodo-1-pentenyl)boronate 、 丙炔酸乙酯 在 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(1E,6E)-pinacol 7-carboethoxy-1,6-heptadienylboronate
  参考文献：
  名称：

  Preparation of polyfunctional olefins and allenes using 1,1-bimetallics of zinc and zirconium

  摘要：

  The hydrozirconation of various alkenylzinc halides with Cp2Zr(H)Cl in dry dichloromethane provides 1,1-dimetalloalkanes of zinc and zirconium which react with aldehydes, providing (E)-alkenes with good to excellent stereoselectivity (up to 98% E). The reaction tolerates the presence of a wide range of functionalities in the dimetallic species as well as in the aldehyde, allowing the preparation of functionalized olefins. Ketones can also be olefinated by these reagents. However, only a moderate stereoselectivity is observed. The hydrozirconation of alkynylzinc halides with CP2Zr(H)Cl gives 1,1-dimetalloalkenes of zinc and zirconium which react with aldehydes, affording allenes. The olefination of alpha,beta-unsaturated aldehydes provides a short access of 1,2,4-trienes.

  DOI：

  10.1021/om00013a020