tert-butyl 2-[(2-chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino]-3,5-dinitrobenzoate | 944088-85-1

• 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: tert-butyl 2-[(2-chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino]-3,5-dinitrobenzoate
• 英文别名: tert-butyl 2-[N-(2-chloroethyl)-N-[2-[(methylsulfonyl)oxy]ethyl]amino]-3,5-dinitrobenzoate；Tert-butyl 2-[2-chloroethyl(2-methylsulfonyloxyethyl)amino]-3,5-dinitrobenzoate；tert-butyl 2-[2-chloroethyl(2-methylsulfonyloxyethyl)amino]-3,5-dinitrobenzoate
• CAS: 944088-85-1
• 化学式: C₁₆H₂₂ClN₃O₉S
• 分子量: 467.884
• InChiKey: UCMOTASUCKRPDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(2-chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino]-3,5-dinitrobenzoate 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.58h， 生成 2-[(2-chloroethyl)-2-[[(2-hydroxyethyl)amino]carbonyl]-4,6-dinitroanilino]ethyl methanesulfonate
  参考文献：
  名称：

  Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104

  摘要：

  Aromatic asymmetric halomesylate mustards are efficiently prepared by reaction of activated aromatic chlorides with aziridine-ethanol/alkali metal halides, followed by mesylation of the haloalcohol. The reaction conditions are sufficiently mild to be compatible with a range of different substituents and protecting groups, including carboxylate and phosphate esters, and have been used in an improved synthesis of the anticancer bromomesylate mustard PR-104, now in clinical trials. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.044
• 作为产物：
  描述：

  tert-butyl 2-chloro-3,5-dinitrobenzoate 在 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 2-[(2-chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino]-3,5-dinitrobenzoate
  参考文献：
  名称：

  Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104

  摘要：

  Aromatic asymmetric halomesylate mustards are efficiently prepared by reaction of activated aromatic chlorides with aziridine-ethanol/alkali metal halides, followed by mesylation of the haloalcohol. The reaction conditions are sufficiently mild to be compatible with a range of different substituents and protecting groups, including carboxylate and phosphate esters, and have been used in an improved synthesis of the anticancer bromomesylate mustard PR-104, now in clinical trials. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.044

文献信息

• WO2008/30112
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104
  作者：Shangjin Yang、Graham J. Atwell、William A. Denny

  DOI：10.1016/j.tet.2007.04.044

  日期：2007.6

  Aromatic asymmetric halomesylate mustards are efficiently prepared by reaction of activated aromatic chlorides with aziridine-ethanol/alkali metal halides, followed by mesylation of the haloalcohol. The reaction conditions are sufficiently mild to be compatible with a range of different substituents and protecting groups, including carboxylate and phosphate esters, and have been used in an improved synthesis of the anticancer bromomesylate mustard PR-104, now in clinical trials. (c) 2007 Elsevier Ltd. All rights reserved.