[(Z)-5-chloro-1-dicyclohexylboranylpent-1-enyl]-trimethylsilane | 338999-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(Z)-5-chloro-1-dicyclohexylboranylpent-1-enyl]-trimethylsilane
• CAS: 338999-04-5
• 化学式: C₂₀H₃₈BClSi
• 分子量: 352.871
• InChiKey: OCSGSLUJOIURAI-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  [(Z)-5-chloro-1-dicyclohexylboranylpent-1-enyl]-trimethylsilane 在 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 12.5h， 生成 2-(5-Chloro-1-trimethylsilanyl-pentyl)-[1,3,2]dioxaborinane
  参考文献：
  名称：

  A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols

  摘要：

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01750-7
• 作为产物：
  描述：

  5-氯戊炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 [(Z)-5-chloro-1-dicyclohexylboranylpent-1-enyl]-trimethylsilane
  参考文献：
  名称：

  A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols

  摘要：

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01750-7

文献信息

• Construction of Terminal Conjugated Enynes: Cu-Mediated Cross-Coupling Reaction of Alkenyldialkylborane with (Trimethylsilyl)ethynyl Bromide
  作者：Masayuki Hoshi、Noritsugu Kawamura、Kazuya Shirakawa

  DOI：10.1055/s-2006-942373

  日期：2006.6

  cross-coupling reaction of (Z)-1-(trimethylsilyl)alk-1-enyldicyclohexylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a small amount of copper(I) iodide and aqueous sodium hydroxide under extremely mild conditions to afford (Z)-l,3-bis(trimethylsilyl)alk-3-en-l-yne with high regio- and stereoselectivity. In addition, treatment of the resulting product with sodium methoxide (1 M) leads

  (E)- 和 (Z)-alk-1-enyl-dialkylborane 与 (三甲基甲硅烷基) 乙炔基溴的交叉偶联反应在催化量的乙酰丙酮铜 (II) 和碱的存在下在极其温和的条件下进行提供具有末端碳-碳三键的共轭烯炔。使用甲醇钠 (1 M) 作为碱不仅可以产生交叉偶联，而且还可以进行脱甲硅烷化，从而得到 (E)- 和 (Z)-alk-3-en-1-ynes，而氢氧化锂一水合物则同时得到 (E)-和 (Z)-alk-3-en-1-ynes。 E)- 和 (Z)-1-(trimethylsilyl)alk-3-en-1-ynes 具有高区域和立体选择性。另一方面，(Z)-1-(三甲基甲硅烷基)烷-1-烯基二环己基硼烷与(三甲基甲硅烷基)乙炔基溴的交叉偶联反应在少量碘化铜(I)和氢氧化钠水溶液的存在下在极其温和的条件下进行，得到(Z)-l,3-bis(trimethylsilyl)alk-3-e
• A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols
  作者：Narayan G. Bhat、Amanda Garza

  DOI：10.1016/s0040-4039(03)01750-7

  日期：2003.9

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.