(E)-3-(3-(adamantan-1-yl)-4-benzyloxyphenyl)acrylaldehyde | 932017-95-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(3-(adamantan-1-yl)-4-benzyloxyphenyl)acrylaldehyde
• 英文别名: (E)-3-[3-(1-adamantyl)-4-phenylmethoxyphenyl]prop-2-enal
• CAS: 932017-95-3
• 化学式: C₂₆H₂₈O₂
• 分子量: 372.507
• InChiKey: RTQPKGXALLUORL-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-(adamantan-1-yl)-4-benzyloxyphenyl)acrylaldehyde 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 potassium carbonate 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成 4'-acetoxy-3'-(adamantan-1-yl)-2-(3-(1,3-dioxoisoindolin-2-yl)propoxy)biphenyl-4-carboxylic acid
  参考文献：
  名称：

  New synthetic approach to atypical retinoids: application of a versatile annulation procedure

  摘要：

  A new approach to an atypical retinoid is presented. The C-15 skeleton was built up by exploiting a step-by-step sequence: the C-9 fragment of an intermediate was homologated by reaction with a C-4 phosphorane, and then submitted to a benzannulation reaction. The last two carbon atoms were inserted by a Wittig reaction with the C-2 phosphorane of ethyl bromoacetate. Manipulation of functional groups was then performed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.038
• 作为产物：
  描述：

  3-(adamantan-1-yl)-4-hydroxybenzaldehyde 在 manganese(IV) oxide 、 sodium hydride 、 红铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 (E)-3-(3-(adamantan-1-yl)-4-benzyloxyphenyl)acrylaldehyde
  参考文献：
  名称：

  New synthetic approach to atypical retinoids: application of a versatile annulation procedure

  摘要：

  A new approach to an atypical retinoid is presented. The C-15 skeleton was built up by exploiting a step-by-step sequence: the C-9 fragment of an intermediate was homologated by reaction with a C-4 phosphorane, and then submitted to a benzannulation reaction. The last two carbon atoms were inserted by a Wittig reaction with the C-2 phosphorane of ethyl bromoacetate. Manipulation of functional groups was then performed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.038

文献信息

• New synthetic approach to atypical retinoids: application of a versatile annulation procedure
  作者：Elisabetta Brenna、Claudio Fuganti、Giovanni Fronza、Francesco G. Gatti、Federico Sala、Stefano Serra

  DOI：10.1016/j.tet.2006.12.038

  日期：2007.3

  A new approach to an atypical retinoid is presented. The C-15 skeleton was built up by exploiting a step-by-step sequence: the C-9 fragment of an intermediate was homologated by reaction with a C-4 phosphorane, and then submitted to a benzannulation reaction. The last two carbon atoms were inserted by a Wittig reaction with the C-2 phosphorane of ethyl bromoacetate. Manipulation of functional groups was then performed. (c) 2007 Elsevier Ltd. All rights reserved.