ClSiMe2C(n-C6H13)CHB(pinacolato) | 1006881-48-6

• 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: ClSiMe2C(n-C6H13)CHB(pinacolato)
• 英文别名: chloro-dimethyl-[(Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oct-1-en-2-yl]silane
• CAS: 1006881-48-6
• 化学式: C₁₆H₃₂BClO₂Si
• 分子量: 330.778
• InChiKey: HDEVOSNNCUAPAU-YPKPFQOOSA-N

物化性质

• 沸点：
  326.9±44.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ClSiMe2C(n-C6H13)CHB(pinacolato) 、 二乙胺 在 三乙胺 作用下， 以 正己烷 为溶剂， 反应 96.0h， 以66%的产率得到Et2NSiMe2C(n-C6H13)CHB(pinacolato)
  参考文献：
  名称：

  Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles

  摘要：

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.

  DOI：

  10.1021/ja073896h
• 作为产物：
  描述：

  (chlorodimethylsilyl)pinacolborane 、 1-辛炔 在 allyl(cyclopentadiene)palladium(II) 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以92%的产率得到ClSiMe2C(n-C6H13)CHB(pinacolato)
  参考文献：
  名称：

  Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles

  摘要：

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.

  DOI：

  10.1021/ja073896h

文献信息

• Synthesis of Cyclic Alkenylborates via Silaboration of Alkynes Followed by Hydrolysis for Utilization in External-Base-Free Cross Coupling
  作者：Toshimichi Ohmura、Kazuyuki Oshima、Michinori Suginome

  DOI：10.1021/om400138u

  日期：2013.5.13

  Cyclic alkenylborates have been synthesized regioselectively via a palladium-catalyzed regioselective silaboration of terminal alkynes with ClMe2Si-B(pin) followed by basic hydrolysis. The cyclic borates undergo cross coupling with 4-iodoanisole in the absence of an external base.