(R,E)-1-(tert-butyl-dimethylsilyl)-6-phenylhex-2-en-1-ol | 1266551-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,E)-1-(tert-butyl-dimethylsilyl)-6-phenylhex-2-en-1-ol
• 英文别名: (E,1R)-1-[tert-butyl(dimethyl)silyl]-6-phenylhex-2-en-1-ol
• CAS: 1266551-30-7
• 化学式: C₁₈H₃₀OSi
• 分子量: 290.521
• InChiKey: XXKAQFIHAZPUOD-GSPCDJLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (R,E)-1-(tert-butyl-dimethylsilyl)-6-phenylhex-2-en-1-ol 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到(R,E)-1-(tert-butyldimethylsilyl)-6-phenylhex-2-en-1-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  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：

  4-苯基丁醛 在 (+)-β-methoxydiisopinocampheylborane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 23.5h， 生成 (S,E)-1-(tert-butyl-dimethylsilyl)-6-phenylhex-2-en-1-ol 、 (R,E)-1-(tert-butyl-dimethylsilyl)-6-phenylhex-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

• 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.