5-benzoylpentanal dimethylacetal | 184680-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoylpentanal dimethylacetal
• 英文别名: 6,6-Dimethoxy-1-phenylhexan-1-one
• CAS: 184680-03-3
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: YXBQEVYEDCLTJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5-benzoylpentanal dimethylacetal 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1S)-6,6-dimethoxy-1-phenylhexan-1-ol
  参考文献：
  名称：

  Studies toward Soraphen A:  An Aldol−Metathesis Avenue to the Macrocyclic Framework

  摘要：

  We describe a convergent approach to soraphen A, 1, that involves coupling of two fragments by an aldol condensation - olefin metathesis sequence. This route permits rapid access to congeners of 1.

  DOI：

  10.1021/ol060882s
• 作为产物：
  描述：

  6,6-dimethoxy-6-phenylhexanal dimethyl acetal 在 硫酸 作用下， 以 水 为溶剂， 反应 0.33h， 以94%的产率得到5-benzoylpentanal dimethylacetal
  参考文献：
  名称：

  A new approach to arylaliphatic 1,5-, 1,6-, and 1,7-dicarbonyl compounds and their monoacetals based on direct anodic oxidation of 1-phenyl- and benzo[c]cycloalkenes

  摘要：

  A new simple approach to omega-benzoylalkanals, 2-(omega-formylalkyl)benzaldehydes, and their monoacetals was developed based on direct anodic oxidation of 1-phenylcycloalkenes and benzo[c]cycloalkenes in methanol followed by acid hydrolysis of the electrolysis products. The target products are obtained in 53-72 % yields.

  DOI：

  10.1007/bf01457781

文献信息

• Oxidative fragmentation of 1-aryl-1-cycloalkenes using cerium(IV) ammonium nitrate (CAN): some novel observations
  作者：Vijay Nair、Sreeletha B Panicker、Siji Thomas、V Santhi、Sindhu Mathai

  DOI：10.1016/s0040-4020(02)00261-2

  日期：2002.4

  1-Phenyl-1-cycloalkenes undergo oxidative fragmentation in presence of CAN in methanol, affording 1,n-dicarbonyl compounds as the major products along with 1,2-dimethoxycycloalkanes. The reaction under deoxygenated conditions afforded the latter in good yields. In the presence of azide ion, fragmentation leading to the corresponding cyanoketones was observed whereas with sultinate only the 1-methoxy-2-sulfonyl cycloalkanes were formed. (C) 2002 Published by Elsevier Science Ltd.
• CAN mediated fragmentation of 1-phenylcycloalkenes: Synthesis of monoacetals of 1,n-dicarbonyl compounds
  作者：Vijay Nair、Sreeletha B. Panicker

  DOI：10.1016/s0040-4039(98)02356-9

  日期：1999.1

  Phenylcycloalkenes undergo facile oxidative fragmentation in presence of CAN in methanol giving ketoacetals of 1,n-dicarbonyl compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Studies toward Soraphen A:  An Aldol−Metathesis Avenue to the Macrocyclic Framework
  作者：Guillaume Vincent、Darren J. Mansfield、Jean-Pierre Vors、Marco A. Ciufolini

  DOI：10.1021/ol060882s

  日期：2006.6.1

  We describe a convergent approach to soraphen A, 1, that involves coupling of two fragments by an aldol condensation - olefin metathesis sequence. This route permits rapid access to congeners of 1.
• A new approach to arylaliphatic 1,5-, 1,6-, and 1,7-dicarbonyl compounds and their monoacetals based on direct anodic oxidation of 1-phenyl- and benzo[c]cycloalkenes
  作者：Yu. N. Ogibin、A. I. Ilovaisky、G. I. Nikishin

  DOI：10.1007/bf01457781

  日期：1996.8

  A new simple approach to omega-benzoylalkanals, 2-(omega-formylalkyl)benzaldehydes, and their monoacetals was developed based on direct anodic oxidation of 1-phenylcycloalkenes and benzo[c]cycloalkenes in methanol followed by acid hydrolysis of the electrolysis products. The target products are obtained in 53-72 % yields.