2-[(Z)-3-(methyl)-1-hexenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1394797-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-[(Z)-3-(methyl)-1-hexenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-[(Z)-3-methylhex-1-enyl]-1,3,2-dioxaborolane
• CAS: 1394797-15-9
• 化学式: C₁₃H₂₅BO₂
• 分子量: 224.151
• InChiKey: LMDRRTLXIIOLPY-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-1-己炔 、 频那醇硼烷 在 C₂₂H₄₅NP₂Ru 作用下， 以 甲苯 为溶剂， 反应 24.08h， 以91%的产率得到2-[(Z)-3-(methyl)-1-hexenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Ruthenium Catalyzed Hydroboration of Terminal Alkynes to Z-Vinylboronates

  摘要：

  The nonclassical ruthenium hydride pincer complex [Ru(PNP)(H)(2)(H-2)] 1 (PNP = 1,3-bis(di-tert-butyl-phosphinomethyl)pyridine) catalyzes the anti-Markovnikov addition of pinacolborane to terminal alkynes yielding Z-vinylboronates at mild conditions. The complex [Ru(PNP)(H)(2)(HBpin)] 2 (HBpin = pinacolborane), which was identified at the end of the reaction and prepared independently, is proposed as the direct precursor to the catalytic cycle involving rearrangement of coordinated alkyne to Z-vinylidene as a key step for the apparent trans-hydroboration.

  DOI：

  10.1021/ja307233p

文献信息

• Ruthenium Catalyzed Hydroboration of Terminal Alkynes to <i>Z</i>-Vinylboronates
  作者：Chidambaram Gunanathan、Markus Hölscher、Fangfang Pan、Walter Leitner

  DOI：10.1021/ja307233p

  日期：2012.9.5

  The nonclassical ruthenium hydride pincer complex [Ru(PNP)(H)(2)(H-2)] 1 (PNP = 1,3-bis(di-tert-butyl-phosphinomethyl)pyridine) catalyzes the anti-Markovnikov addition of pinacolborane to terminal alkynes yielding Z-vinylboronates at mild conditions. The complex [Ru(PNP)(H)(2)(HBpin)] 2 (HBpin = pinacolborane), which was identified at the end of the reaction and prepared independently, is proposed as the direct precursor to the catalytic cycle involving rearrangement of coordinated alkyne to Z-vinylidene as a key step for the apparent trans-hydroboration.