(5RS,6RS)-6-(tert-butyldimethylsiloxy)deca-1,9-dien-5-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: (5RS,6RS)-6-(tert-butyldimethylsiloxy)deca-1,9-dien-5-ol
• 英文别名: (5R,6R)-6-[tert-butyl(dimethyl)silyl]oxydeca-1,9-dien-5-ol
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: GFTGBSROIRBGOV-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  间溴苯甲醚 、 (5RS,6RS)-6-(tert-butyldimethylsiloxy)deca-1,9-dien-5-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 双(2-二苯基磷苯基)醚 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到tert-butyl-{(1RS)-1-[(2RS,5RS)-5-(3-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-enyloxy}dimethylsilane
  参考文献：
  名称：

  Synthesis of Fused-Ring and Attached-Ring bis-Tetrahydrofurans via Pd-Catalyzed Carboetherification

  摘要：

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.

  DOI：

  10.1021/ol900594h
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (5R,6R)-5,6-dihydroxydeca-1,9-diene 在 正丁基锂 、 咪唑 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以44%的产率得到(5RS,6RS)-6-(tert-butyldimethylsiloxy)deca-1,9-dien-5-ol
  参考文献：
  名称：

  Synthesis of Fused-Ring and Attached-Ring bis-Tetrahydrofurans via Pd-Catalyzed Carboetherification

  摘要：

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.

  DOI：

  10.1021/ol900594h

文献信息

• Synthesis of Fused-Ring and Attached-Ring <i>bis</i>-Tetrahydrofurans via Pd-Catalyzed Carboetherification
  作者：Amanda F. Ward、John P. Wolfe

  DOI：10.1021/ol900594h

  日期：2009.5.21

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.