ditert-butyl (2,4-dinitronaphthalen-1-yl)-malonate | 897918-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ditert-butyl (2,4-dinitronaphthalen-1-yl)-malonate
• 英文别名: Ditert-butyl 2-(2,4-dinitronaphthalen-1-yl)propanedioate
• CAS: 897918-35-3
• 化学式: C₂₁H₂₄N₂O₈
• 分子量: 432.43
• InChiKey: RPSIDEQRUDYHPH-UHFFFAOYSA-N

物化性质

• 熔点：
  116-118 °C
• 沸点：
  544.9±50.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2,4-dinitronaphthalen-1-yl)-malonate 在 sodium sulfide 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (4-amino-2-nitronaphthalen-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
• 作为产物：
  描述：

  丙二酸二叔丁酯 、 氯硝萘 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到ditert-butyl (2,4-dinitronaphthalen-1-yl)-malonate
  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.