(Z)-1-(trimethylsilyloxy)hex-2-ene | 139332-49-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-1-(trimethylsilyloxy)hex-2-ene
• 英文别名: 2-Hexen-1-ol, (Z)-, TMS derivative；[(Z)-hex-2-enoxy]-trimethylsilane
• CAS: 139332-49-3
• 化学式: C₉H₂₀OSi
• 分子量: 172.343
• InChiKey: JLSKQCUTNMNICQ-FPLPWBNLSA-N

物化性质

• 沸点：
  177.6±9.0 °C(Predicted)
• 密度：
  0.809±0.06 g/cm3(Predicted)
• 保留指数：
  1001.5

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-(trimethylsilyloxy)hex-2-ene 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[((Z)-hex-2-enyl)oxy]-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Carbohydrates as chiral auxiliaries: synthesis of 2-hydroxy-β-D-glucopyranosides

  摘要：

  A new 2-step, 1-pot procedure for the stereoselective glycosylation of allylic alcohols with 1,2-di-O-benzoyl-beta-D-glucopyranosides to produce 2-hydroxy-beta-D-glucopyranosides has been developed. The required precursor for the glycosylation was readily obtained from tri-O-benzyl-D-glucal in 2 steps (91% overall).

  DOI：

  10.1016/0040-4039(91)80479-p
• 作为产物：
  描述：

  (hex-2-yn-1-yloxy)trimethylsilane 在 silica-supported frustrated Lewis pair 3a (HBC₆F₅)2; (4-hydroxyphenyl)biphenylphosphine; [(SiO)2AliBuEt₂O)]) 作用下， 以 正戊烷 为溶剂， 80.0 ℃ 、1.0 MPa 条件下， 反应 16.0h， 生成 (Z)-1-(trimethylsilyloxy)hex-2-ene
  参考文献：
  名称：

  Development of silica-supported frustrated Lewis pairs: highly active transition metal-free catalysts for the Z-selective reduction of alkynes

  摘要：

  支持的Lewis酸/碱体系已经被制备和表征。

  DOI：

  10.1039/c5cy01372k

文献信息

• The catalytic Friedel–Crafts alkylation reaction of aromatic compounds with benzyl or allyl silyl ethers using Cl2Si(OTf)2 or Hf(OTf)4
  作者：Isamu Shiina、Masahiko Suzuki

  DOI：10.1016/s0040-4039(02)01376-x

  日期：2002.9

  The Friedel-Crafts alkylation reaction of various aromatic compounds with benzyl or allyl silyl ethers is effectively promoted under mild reaction conditions using Lewis acid catalysts. A mixture of the desired phenyltolylmethanes is obtained in 80% yield from toluene with benzyl dimethylsilyl or trimethylsilyl ether at 50degreesC in the presence of a catalytic amount of Cl2Si(OTf)(2) or Hf(OTf)(2). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Carbohydrates as chiral auxiliaries: synthesis of 2-hydroxy-β-D-glucopyranosides
  作者：André B. Charette、Jean-François Marcoux、Bernard Côté

  DOI：10.1016/0040-4039(91)80479-p

  日期：1991.12

  A new 2-step, 1-pot procedure for the stereoselective glycosylation of allylic alcohols with 1,2-di-O-benzoyl-beta-D-glucopyranosides to produce 2-hydroxy-beta-D-glucopyranosides has been developed. The required precursor for the glycosylation was readily obtained from tri-O-benzyl-D-glucal in 2 steps (91% overall).
• Development of silica-supported frustrated Lewis pairs: highly active transition metal-free catalysts for the Z-selective reduction of alkynes
  作者：Kai C. Szeto、Wissam Sahyoun、Nicolas Merle、Jessica Llop Castelbou、Nicolas Popoff、Frédéric Lefebvre、Jean Raynaud、Cyril Godard、Carmen Claver、Laurent Delevoye、Régis M. Gauvin、Mostafa Taoufik

  DOI：10.1039/c5cy01372k

  日期：——

  Supported Lewis acid/base systems based have been prepared and characterized.

  支持的Lewis酸/碱体系已经被制备和表征。