2-[(E,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-5-methyloct-2-enyl]benzoic acid | 314273-49-9

• 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: 2-[(E,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-5-methyloct-2-enyl]benzoic acid
• CAS: 314273-49-9
• 化学式: C₂₂H₃₆O₄Si
• 分子量: 392.611
• InChiKey: ZDPLCOGDUZPKCQ-TVYZCSMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-5-methyloct-2-enyl]benzoic acid 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 16.0h， 以64%的产率得到(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：

  2-溴甲基苯甲酸甲酯 在 lithium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 42.0h， 生成 2-[(E,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-5-methyloct-2-enyl]benzoic acid
  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.