2-methyl-5-triethylsilanyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-methyl-5-triethylsilanyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester
• 英文别名: methyl 2-ethenyl-5-methyl-2-triethylsilyl-3H-furan-4-carboxylate
• 化学式: C₁₅H₂₆O₃Si
• 分子量: 282.455
• InChiKey: CWHXKIBMSRCWNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-6-Acetoxy-2-acetyl-4-triethylsilanyl-hex-4-enoic acid methyl ester 在 palladium diacetate 、 sodium hydride 、 三苯基膦 作用下， 生成 2-methyl-5-triethylsilanyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Silicon effect favoring the formation of a cyclopentene via palladium-catalyzed 5-endo-trig cyclisation

  摘要：

  A silyl substituted cyclopentene was prepared from acyclic triethylsilyl pentenol derivatives via pallladium-catalyzed 5-endo-trig process. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02208-4

文献信息

• The silicon effect on the regioselectivity of the Tsuji-Trost reaction. Experimental and theoretical approaches
  作者：Vicenç Branchadell、Marcial Moreno-Mañas、Roser Pleixats、Serge Thorimbert、Claude Commandeur、Cécile Boglio、Max Malacria

  DOI：10.1016/s0022-328x(03)00664-8

  日期：2003.12

  Regioselectivity of the Tsuji-Trost reaction on allyl acetates and carbonates substituted with silyl groups at the olefinic moiety has been analyzed. Silicon atom in the central carbon atom increases the stability of the intermediate pi-allylpalladium cation with respect to the isomeric pi-allylpalladium cation featuring the silicon in a terminal carbon atom. (C) 2003 Elsevier B.V. All rights reserved.
• Silicon effect favoring the formation of a cyclopentene via palladium-catalyzed 5-endo-trig cyclisation
  作者：Serge Thorimbert、Max Malacria

  DOI：10.1016/s0040-4039(98)02208-4

  日期：1998.12

  A silyl substituted cyclopentene was prepared from acyclic triethylsilyl pentenol derivatives via pallladium-catalyzed 5-endo-trig process. (C) 1998 Elsevier Science Ltd. All rights reserved.