1-phenylpropan-2-yl (tert-butoxycarbonyl)sulfamate | 1375958-80-7

• 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: 1-phenylpropan-2-yl (tert-butoxycarbonyl)sulfamate
• CAS: 1375958-80-7
• 化学式: C₁₄H₂₁NO₅S
• 分子量: 315.39
• InChiKey: OENRHKMMBZTTNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-phenylpropan-2-yl (tert-butoxycarbonyl)sulfamate 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以4.3 g的产率得到1-phenylpropan-2-yl sulfamate
  参考文献：
  名称：

  N-(tert-Butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide: A Convenient Sulfamoylation Reagent for Alcohols

  摘要：

  A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tertbutoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.

  DOI：

  10.1021/ol3009683
• 作为产物：
  描述：

  1-苯基-2-丙醇 、 1-aza-4-azoniabicyclo[2.2.2]octan-4-ylsulfonyl(tert-butoxycarbonyl)azanido 1,4-diazabicyclo[2.2.2]octane monohydrochloride 以 乙腈 为溶剂， 反应 0.5h， 生成 1-phenylpropan-2-yl (tert-butoxycarbonyl)sulfamate
  参考文献：
  名称：

  N-(tert-Butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide: A Convenient Sulfamoylation Reagent for Alcohols

  摘要：

  A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tertbutoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.

  DOI：

  10.1021/ol3009683

文献信息

• Preparation of Sulfamates and Sulfamides Using a Selective Sulfamoylation Agent
  作者：Hai-Ming Wang、Chao-Dong Xiong、Xiao-Qu Chen、Chun Hu、Dong-Yu Wang

  DOI：10.1021/acs.orglett.1c00504

  日期：2021.4.2

  Sulfamates and sulfamides are prevalent in biological molecules, but their universal synthetic methods are limited. We herein report a sulfamoylation agent with high solubility and shelf stability. Various sulfamates and sulfamides can be synthesized directly from alcohols or amines by employing this agent with high selectivity and high yields. This protocol was also successfully used for late-stage

  氨基磺酸盐和磺酰胺在生物分子中普遍存在，但它们的通用合成方法受到限制。我们在本文中报道了具有高溶解度和贮存稳定性的氨磺酰化剂。通过以高选择性和高收率使用该试剂，可以直接从醇或胺合成各种氨基磺酸盐和磺酰胺。该方案也已成功用于含有羟基或氨基基团的药物的后期氨磺酰化反应。
• 一种氨基磺酸酯的制备方法
  申请人：上海交通大学

  公开号：CN114478373B

  公开（公告）日：2023-11-17

  本发明涉及一种氨基磺酸酯的制备方法。具体地，本发明公开了一种氨基磺酰化试剂，具有廉价易得、溶解度好、高稳定性等优点。使用所述试剂可高选择性地实现对羟基的氨基磺酰化修饰，反应条件温和，操作简单，可放大量。所得产物具有收率高、副产物少、纯度高等优势。