(2-triphenylsilyl)-2-propenyl alcohol | 101844-28-4

• 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: (2-triphenylsilyl)-2-propenyl alcohol
• 英文别名: 2-Triphenylsilylprop-2-en-1-ol
• CAS: 101844-28-4
• 化学式: C₂₁H₂₀OSi
• 分子量: 316.475
• InChiKey: GVSDVGXGZVGLOW-UHFFFAOYSA-N

物化性质

• 沸点：
  428.7±37.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-triphenylsilyl)-2-propenyl alcohol 、 对氯苯异氰酸酯 以 苯 为溶剂， 反应 0.5h， 以84%的产率得到(2-triphenylsilyl)-2-propenyl p-chlorophenyl carbamate
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d
• 作为产物：
  描述：

  聚合甲醛 、 1-溴乙烯基(三苯基)硅烷 在 正丁基锂 作用下， 生成 (2-triphenylsilyl)-2-propenyl alcohol
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d

文献信息

• Allylsilanes in organic synthesis; convenient preparation of synthetic intermediates by catalytic hydrosilation of acetylenic alcohols
  作者：Patrick J. Murphy、John L. Spencer、Garry Procter

  DOI：10.1016/s0040-4039(00)94428-9

  日期：1990.1

  Synthetically useful vinylslane-alcohols such as (1) can be easily prepared by the catalytic hydrosilation of the appropriate acetylenic alcohols in high yield, and with excellent regioand stereoselectivity, without the need to protect the hydroxyl group.

  可通过合适的炔属醇的催化硅氢化作用以高收率，具有优异的区域选择性和立体选择性而无需保护羟基的情况下，容易地制备合成有用的乙烯基sl烷醇（如（1））。
• Hydrosilylation of the CC triple bond by phenyl- and thienyl-silanes
  作者：E. Lukevics、R.Ya. Sturkovich、O.A. Pudova

  DOI：10.1016/0022-328x(85)87330-7

  日期：1985.9
• MURPHY, PATRICK J.;SPENCER, JOHN L.;PROCTER, GARRY, TETRAHEDRON. LETT., 31,(1990) N, C. 1051-1054
  作者：MURPHY, PATRICK J.、SPENCER, JOHN L.、PROCTER, GARRY

  DOI：——

  日期：——