isopropyl tosylcarbamate | 18303-02-1

• 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: isopropyl tosylcarbamate
• 英文别名: Carbamic acid, [(4-methylphenyl)sulfonyl]-, 1-methylethyl ester；propan-2-yl N-(4-methylphenyl)sulfonylcarbamate
• CAS: 18303-02-1
• 化学式: C₁₁H₁₅NO₄S
• 分子量: 257.31
• InChiKey: FOKWWPWMZYWNKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲苯磺酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 生成 isopropyl tosylcarbamate
  参考文献：
  名称：

  Microwave Promoted Transcarbamylation Reaction of Sulfonylcarbamates under Continuous-Flow Conditions

  摘要：

  Successful conditions for the transcarbamylation/transesterification reaction of sulfonylcarbamates with alcohols by microwave heating under continuous flow conditions were developed. After optimization of the processes, two series of O-alkylsulfonylcarbamates were obtained in high yields and purities using microwave transparent borosilicate tube reactors. In order to also illustrate the usefulness of the protocol in a medicinal chemistry context, the methodology was used for the synthesis of three angiotensin II type 2 receptor ligands.

  DOI：

  10.1021/acs.oprd.5b00323

文献信息

• Sulfonyl Azides as Precursors in Ligand-Free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides
  作者：Shiao Y. Chow、Marc Y. Stevens、Luke R. Odell

  DOI：10.1021/acs.joc.5b02755

  日期：2016.4.1

  An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)6, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl

  已经开发了使用钯催化的羰基化方案从磺酰叠氮化物有效合成磺酰氨基甲酸酯和磺酰脲的方法。使用两腔室系统，从Mo（CO）6异位释放的磺酰叠氮化物PdCl 2和CO气体被组装以原位生成磺酰基异氰酸酯，并且醇和芳基胺被用作亲核试剂以提供广泛的应用范围氨基甲酸酯磺酸盐和磺酰脲。还开发了通过亲核取代从磺酰基叠氮化物和胺直接形成取代的磺酰胺的方案。
• N-arylsulfonyl carbamates
  申请人：Monsanto Company

  公开号：US03933894A1

  公开（公告）日：1976-01-20

  The present invention relates to amine, alkali metal and alkaline earth metal salts of N-benzene sulfonyl carbamic acid esters and to lower alkenyl N-benzene sulfonyl carbamates. These compounds are useful as herbicides.

  本发明涉及N-苯磺酰基氨基、碱金属和碱土金属盐以及较低烯基N-苯磺酰基氨基甲酸酯，这些化合物可用作除草剂。
• Synthesis of arylsulfonylcarbamic acid derivatives using a new, phosgene-free method
  作者：Gábor Besenyei、Sándor Németh、László I. Simándi

  DOI：10.1016/s0040-4039(00)93568-8

  日期：1991.10

  Arylsulfonylcarbamic acid esters, thioesters, and amides, 3, have been prepared via catalytic carbonylation of alkali metal salts of N-chloroarylsulfonamides, 1, and treatment of the reaction mixture with R1XH (XO, S, NR2).

  芳族磺酰基氨基甲酸酯，硫代酸酯和酰胺3，是通过对N-氯芳基磺酰胺1的碱金属盐进行催化羰基化，并用R 1 XH（X = O，S，NR 2）处理反应混合物来制备的。
• US3933894A
  申请人：——

  公开号：US3933894A

  公开（公告）日：1976-01-20
• Microwave Promoted Transcarbamylation Reaction of Sulfonylcarbamates under Continuous-Flow Conditions
  作者：Ilze Kumpiņa、Rebecka Isaksson、Jonas Sävmarker、Johan Wannberg、Mats Larhed

  DOI：10.1021/acs.oprd.5b00323

  日期：2016.2.19

  Successful conditions for the transcarbamylation/transesterification reaction of sulfonylcarbamates with alcohols by microwave heating under continuous flow conditions were developed. After optimization of the processes, two series of O-alkylsulfonylcarbamates were obtained in high yields and purities using microwave transparent borosilicate tube reactors. In order to also illustrate the usefulness of the protocol in a medicinal chemistry context, the methodology was used for the synthesis of three angiotensin II type 2 receptor ligands.