3-acetoxy-2-(4-benzyloxy-2-nitrophenyl)propan-1-yl methanesulfonate | 132628-57-0

• 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: 3-acetoxy-2-(4-benzyloxy-2-nitrophenyl)propan-1-yl methanesulfonate
• 英文别名: [3-methylsulfonyloxy-2-(2-nitro-4-phenylmethoxyphenyl)propyl] acetate
• CAS: 132628-57-0
• 化学式: C₁₉H₂₁NO₈S
• 分子量: 423.444
• InChiKey: QJHIQVVHPLZMKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122.04
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-acetoxy-2-(4-benzyloxy-2-nitrophenyl)propan-1-yl methanesulfonate 在 platinum(IV) oxide 咪唑 、 磺酰氯 、 氢气 、 硝酸 、 乙酸酐 、 1,8-双二甲氨基萘 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 、 copper(II) oxide 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -78.0~25.0 ℃ 、303.98 kPa 条件下， 反应 58.41h， 生成 methyl 5-amino-6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-1H-indole-4-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-(2-硝基-4-苯基甲氧基苯基)丙烷-1,3-二醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-acetoxy-2-(4-benzyloxy-2-nitrophenyl)propan-1-yl methanesulfonate
  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

• First total synthesis of dl-duocarmycin A
  作者：Yasumichi Fukuda、Kazuhiko Nakatani、Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4039(00)97151-x

  日期：1990.1
• FUKUDA, YASUMICHI;NAKATANI, KAZUHIKO;ITO, YOSHIO;TERASHIMA, SHIRO, TETRAHEDRON LETT., 31,(1990) N6, C. 6699-6702
  作者：FUKUDA, YASUMICHI、NAKATANI, KAZUHIKO、ITO, YOSHIO、TERASHIMA, SHIRO

  DOI：——

  日期：——
• 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.