4'-acetoxy-3'-(adamantan-1-yl)-2-(3-(1,3-dioxoisoindolin-2-yl)propoxy)biphenyl-4-carboxylic acid | 932017-98-6

• 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: 4'-acetoxy-3'-(adamantan-1-yl)-2-(3-(1,3-dioxoisoindolin-2-yl)propoxy)biphenyl-4-carboxylic acid
• CAS: 932017-98-6
• 化学式: C₃₆H₃₅NO₇
• 分子量: 593.676
• InChiKey: XATXBQYZMITQFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110.21
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4'-acetoxy-3'-(adamantan-1-yl)-2-(3-(1,3-dioxoisoindolin-2-yl)propoxy)biphenyl-4-carboxylic acid 在 氯甲酸乙酯 、 三乙胺 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以72%的产率得到3-(adamantan-1-yl)-2'-(3-(1-hydroxy-3-oxoisoindolin-2-yl)propoxy)-4'-(hydroxymethyl)biphenyl-4-yl acetate
  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：

  (3E,5E)-6-(3-(adamantan-1-yl)-4-benzyloxyphenyl)-3-(ethoxycarbonyl)hexa-3,5-dienoic acid 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 为溶剂， 反应 4.5h， 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