N¹-BOC-N³-benzyl,N³-(2-chloroethyl) sulfamide | 182925-57-1

• 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: N¹-BOC-N³-benzyl,N³-(2-chloroethyl) sulfamide
• 英文别名: tert-butyl N-(benzylsulfamoyl)-N-(2-chloroethyl)carbamate
• CAS: 182925-57-1
• 化学式: C₁₄H₂₁ClN₂O₄S
• 分子量: 348.851
• InChiKey: LLLCAFCUMOURCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N¹-BOC-N³-benzyl,N³-(2-chloroethyl) sulfamide 在 甲酸 、 三氟乙酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)—I. Synthesis, structure, and pharmacological evaluation (preliminary results)

  摘要：

  A new series of alkylating agents, 2-chloroethylnitrososulfamides (CENS), were developed on the model of 2-chloroethylnitrosoureas. Starting from chlorosulfonyl isocyanate, a four-step synthesis (carbamoylation-sulfamoylation, Mitsunobu alkylation, deprotection, and nitrosation) gives the title compounds in a 47-58% overall yield. The selection of the nitrosation site can be directed through an alternative route. The pharmacological evaluation shows a significant oncostatic activity towards both A549 and MCF7 cell lines. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00118-6
• 作为产物：
  描述：

  苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 N¹-BOC-N³-benzyl,N³-(2-chloroethyl) sulfamide
  参考文献：
  名称：

  A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)—I. Synthesis, structure, and pharmacological evaluation (preliminary results)

  摘要：

  A new series of alkylating agents, 2-chloroethylnitrososulfamides (CENS), were developed on the model of 2-chloroethylnitrosoureas. Starting from chlorosulfonyl isocyanate, a four-step synthesis (carbamoylation-sulfamoylation, Mitsunobu alkylation, deprotection, and nitrosation) gives the title compounds in a 47-58% overall yield. The selection of the nitrosation site can be directed through an alternative route. The pharmacological evaluation shows a significant oncostatic activity towards both A549 and MCF7 cell lines. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00118-6

文献信息

• Synthesis of 1,2,5-Thiadiazolidines 1,1-dioxides (Cyclosulfamides) Starting from Amino Acids and Chlorosulfonyl Isocyanate
  作者：Zine Regaı̈nia、Mohamed Abdaoui、Nour-Eddine Aouf、Georges Dewynter、Jean-Louis Montero

  DOI：10.1016/s0040-4020(99)01025-x

  日期：2000.1

  substituted by the BOC group. These compounds are synthesized starting from chlorosulfonyl isocyanate and nitrogen mustards or amino acids. The derivatization of amino acids can lead to an alkyl group on C-4 with a well-defined configuration; in this case the N5 position was protected by a benzyl group. These compounds are valuable tools for asymmetric synthesis.

  我们在这里报告了对五种由BOC基团取代的五元环硫酰胺（1,2,5-噻二唑烷1,1-二氧化物）N 2的实际访问方法。这些化合物是从氯磺酰基异氰酸酯和氮芥或氨基酸开始合成的。氨基酸的衍生化可以导致C-4上的烷基具有明确定义的结构；在这种情况下，N 5位被苄基保护。这些化合物是用于不对称合成的有价值的工具。