benzoic acid 7-formyl-oct-7-enyl ester | 832688-88-7

• 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: benzoic acid 7-formyl-oct-7-enyl ester
• 英文别名: 7-Formyloct-7-en-1-yl benzoate；7-formyloct-7-enyl benzoate
• CAS: 832688-88-7
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: BFOZDDMFOOVNBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzoic acid 7-formyl-oct-7-enyl ester 在 sodium tetrahydroborate 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 Benzoic acid 7-bromomethyl-oct-7-enyl 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：

  1,8-辛二醇 在 4-二甲氨基吡啶 、 草酰氯 、 盐酸二甲胺 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 benzoic acid 7-formyl-oct-7-enyl 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

文献信息

• Mono- and Bis-Acrolein Derivatives by Reliable and Efficient One-Step Methylenation of Aldehyde Precursors
  作者：Leo Paquette、Kallol Basu、Jonathan Richards

  DOI：10.1055/s-2004-834866

  日期：——

  A series of aldehydes carrying different functional groups was transformed directly into the α-methylene derivatives. Dialdehydes behaved comparably at both active sites. When keto aldehydes are involved, excellent levels of chemoselectivity are observed, with the ketone substructures exhibiting no sign of reactivity.

  一系列带有不同官能团的醛被直接转化为δ-亚甲基衍生物。二醛在两个活性位点的表现相当。当涉及酮醛时，可观察到极好的化学选择性，而酮基结构则没有反应迹象。
• Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A
  作者：Stefan Pichlmair、Manuel de Lera Ruiz、Kallol Basu、Leo A. Paquette

  DOI：10.1016/j.tet.2005.11.096

  日期：2006.5

  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.