methyl 3-methoxy-2-(1-methoxycarbonylethyl)amino-6-methylbenzoate | 157485-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-methoxy-2-(1-methoxycarbonylethyl)amino-6-methylbenzoate
• CAS: 157485-01-3
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: TWYKKPNCPIUWJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3-methoxy-2-(1-methoxycarbonylethyl)amino-6-methylbenzoate 在 正丁基锂 、 乙酸酐 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl 2,3-dihydro-2,4-dimethyl-1-formyl-7-methoxy-3-oxo-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer

  摘要：

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.

  DOI：

  10.1016/s0040-4020(01)86993-3
• 作为产物：
  描述：

  2-甲氧基-5-甲基苯胺 在 氢氧化钾 、 氯化亚砜 、 双氧水 、 四氯化钛 、 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 34.0h， 生成 methyl 3-methoxy-2-(1-methoxycarbonylethyl)amino-6-methylbenzoate
  参考文献：
  名称：

  Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer

  摘要：

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.

  DOI：

  10.1016/s0040-4020(01)86993-3

文献信息

• Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer
  作者：Yasumichi Fukuda、Yoshio Itoh、Kazuhiko Nakatani、Terashima Shiro

  DOI：10.1016/s0040-4020(01)86993-3

  日期：1994.2

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.