[(3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhept-6-enyl] 2-prop-2-enylbenzoate | 314273-43-3

• 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: [(3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhept-6-enyl] 2-prop-2-enylbenzoate
• CAS: 314273-43-3
• 化学式: C₂₄H₃₈O₃Si
• 分子量: 402.649
• InChiKey: ZYLBOYDRYPGIEO-KNQAVFIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhept-6-enyl] 2-prop-2-enylbenzoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (6S,7R,9Z)-6-[tert-butyl(dimethyl)silyl]oxy-7-methyl-3-oxabicyclo[10.4.0]hexadeca-1(16),9,12,14-tetraen-2-one 、 (6S,7R,9E)-6-[tert-butyl(dimethyl)silyl]oxy-7-methyl-3-oxabicyclo[10.4.0]hexadeca-1(16),9,12,14-tetraen-2-one
  参考文献：
  名称：

  Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization

  摘要：

  Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01420-9
• 作为产物：
  描述：

  (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhept-6-en-1-ol 在 吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯基膦 、 lithium chloride 、 偶氮二甲酸二乙酯 作用下， 以 N-甲基吡咯烷酮 、 乙醚 、 二氯甲烷 为溶剂， 反应 53.5h， 生成 [(3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhept-6-enyl] 2-prop-2-enylbenzoate
  参考文献：
  名称：

  Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization

  摘要：

  Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01420-9

文献信息

• Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization
  作者：John T Feutrill、Georgina A Holloway、Ferdows Hilli、Helmut M Hügel、Mark A Rizzacasa

  DOI：10.1016/s0040-4039(00)01420-9

  日期：2000.10

  Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd. All rights reserved.