(E)-1-(tert-butyldimethylsilyl)-4-methylpent-2-en-1-ol

• 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: (E)-1-(tert-butyldimethylsilyl)-4-methylpent-2-en-1-ol
• 英文别名: (E)-1-[tert-butyl(dimethyl)silyl]-4-methylpent-2-en-1-ol
• 化学式: C₁₂H₂₆OSi
• 分子量: 214.423
• InChiKey: YNZFVAUPLNMERR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (E)-1-(tert-butyldimethylsilyl)-4-methylpent-2-en-1-ol 、 对硝基苯甲酸 在 4-二甲氨基吡啶 、 ethylene dichloride hydrochloride 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以100%的产率得到(E)-1-(tert-butyldimethylsilyl)-4-methylpent-2-enyl 4-nitrobenzoate
  参考文献：
  名称：

  Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes

  摘要：

  A novel silyl group-directed anti-S(N)2' reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of alpha-hydroxy-alpha-alkenylsilanes with a TBS or TIPS group gave the anti-S(N)2' product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.080
• 作为产物：
  描述：

  dimethyl 2-(tert-butyldimethylsilyl)-2-oxoethylphosphonate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 4.0h， 生成 (E)-1-(tert-butyldimethylsilyl)-4-methylpent-2-en-1-ol
  参考文献：
  名称：

  Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes

  摘要：

  A novel silyl group-directed anti-S(N)2' reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of alpha-hydroxy-alpha-alkenylsilanes with a TBS or TIPS group gave the anti-S(N)2' product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.080

文献信息

• Enantioselective Reduction of α,β-Unsaturated Acylsilanes by Chiral Lithium Amides
  作者：Kei Takeda、Yuji Ohnishi、Toru Koizumi

  DOI：10.1021/ol990574c

  日期：1999.7.1

  Reaction of beta-substituted acryloylsilanes I with lithium amides II affords a-silyl allylic alcohols III in high enantiomeric excess (>99%) via formal hydride transfer from the chiral lithium amide.
• Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes
  作者：Masato Higashino、Naoko Ikeda、Tetsuro Shinada、Kazuhiko Sakaguchi、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2010.11.080

  日期：2011.1

  A novel silyl group-directed anti-S(N)2' reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of alpha-hydroxy-alpha-alkenylsilanes with a TBS or TIPS group gave the anti-S(N)2' product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group. (C) 2010 Elsevier Ltd. All rights reserved.