[4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]acetic acid | 897918-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]acetic acid
• 英文别名: 2-(4-Acetyloxy-2-ethoxycarbonylnaphthalen-1-yl)acetic acid
• CAS: 897918-41-1
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: ULDLBIXAVYUMSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]acetic acid 在 sodium hydroxide 、 乙醇 、 叠氮磷酸二苯酯 、 硼烷 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 77.0h， 生成 2-(4-benzyloxy-2-aminonaphthalen-1-yl)ethyl triphenylmethyl ether
  参考文献：
  名称：

  Efficient Synthesis of Achiral seco-Cyclopropylbenz[2,3-e]indoline Analogues:  [4-Amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride and [4-Hydroxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride

  摘要：

  Achiral seco-aminocyclopropylbenz[ 2,3-e] indoline and secohydroxycyclopropylbenz[ 2,3-e] indoline ( seco-CBI) analogues of the duocarmycins and CC-1065, e. g., 7 and 8, are potent anticancer agents. This paper describes significantly improved synthetic strategies for preparing these compounds. Starting from Martius acid ( 9), the new strategy gave a 13-fold increase in the overall yield of 7, and the use of ditertbutyl malonate was economically beneficial. For compound 8, the new strategy employed an Emmons-Horner reaction, followed by a Stobbe condensation, and the overall yield was improved 15-fold.

  DOI：

  10.1021/jo060501o
• 作为产物：
  描述：

  benzyl [4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]acetate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 2.0h， 以88%的产率得到[4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]acetic acid
  参考文献：
  名称：

  Efficient Synthesis of Achiral seco-Cyclopropylbenz[2,3-e]indoline Analogues:  [4-Amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride and [4-Hydroxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride

  摘要：

  Achiral seco-aminocyclopropylbenz[ 2,3-e] indoline and secohydroxycyclopropylbenz[ 2,3-e] indoline ( seco-CBI) analogues of the duocarmycins and CC-1065, e. g., 7 and 8, are potent anticancer agents. This paper describes significantly improved synthetic strategies for preparing these compounds. Starting from Martius acid ( 9), the new strategy gave a 13-fold increase in the overall yield of 7, and the use of ditertbutyl malonate was economically beneficial. For compound 8, the new strategy employed an Emmons-Horner reaction, followed by a Stobbe condensation, and the overall yield was improved 15-fold.

  DOI：

  10.1021/jo060501o

文献信息

• Efficient Synthesis of Achiral <i>s</i><i>eco</i>-Cyclopropylbenz[2,3-<i>e</i>]indoline Analogues:  [4-Amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride and [4-Hydroxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride
  作者：Atsushi Sato、Adrienne Scott、Tetsuji Asao、Moses Lee

  DOI：10.1021/jo060501o

  日期：2006.6.1

  Achiral seco-aminocyclopropylbenz[ 2,3-e] indoline and secohydroxycyclopropylbenz[ 2,3-e] indoline ( seco-CBI) analogues of the duocarmycins and CC-1065, e. g., 7 and 8, are potent anticancer agents. This paper describes significantly improved synthetic strategies for preparing these compounds. Starting from Martius acid ( 9), the new strategy gave a 13-fold increase in the overall yield of 7, and the use of ditertbutyl malonate was economically beneficial. For compound 8, the new strategy employed an Emmons-Horner reaction, followed by a Stobbe condensation, and the overall yield was improved 15-fold.