{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol | 896110-49-9

• 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: {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol
• 英文别名: [(1S,3Z,4R)-4-(methoxymethoxy)-2-methylidene-3-(4-phenylmethoxybutylidene)cyclopentyl]methanol
• CAS: 896110-49-9
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: OSYXMXGRBPSHRM-ATCREUKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol 、 2-carbethoxy-2-methylcyclohexanone 、 叔丁基二苯基氯硅烷 生成 (S)-3-(tert-butyldiphenylsilyloxymethyl)-3-methylcyclopent-1-enecarboxylic acid {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methyl ester 、 (R)-3-(tert-butyldiphenylsilyloxymethyl)-3-methylcyclopent-1-enecarboxylic acid {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methyl ester
  参考文献：
  名称：

  Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

  摘要：

  A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.096
• 作为产物：
  描述：

  (E)-(4S,6R)-11-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-undec-2-en-7-yn-6-ol 在 palladium diacetate 正丁基锂 、 N,N-双(苯基亚甲基)-1,2-乙二胺 、 四丁基氟化铵 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 88.75h， 生成 {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol
  参考文献：
  名称：

  Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

  摘要：

  A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.096