2-allylphenylsulfamate | 691397-32-7

• 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: 2-allylphenylsulfamate
• 英文别名: (2-Prop-2-enylphenyl) sulfamate
• CAS: 691397-32-7
• 化学式: C₉H₁₁NO₃S
• 分子量: 213.257
• InChiKey: OSHLPQHVTMEIMU-UHFFFAOYSA-N

物化性质

• 沸点：
  354.8±45.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-allylphenylsulfamate 在 dirhodium tetraacetate 、 碘苯二乙酸 、 magnesium oxide 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-benzyl-5-methoxy-5,6-dihydro-4H-1,2lambda6,3-benzoxathiazocine 2,2-dioxide
  参考文献：
  名称：

  Exploring New Uses for C−H Amination:  Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates

  摘要：

  Benzene-fused cyclic sulfamates are prepared from ortho-substituted phenolic starting materials through selective C-H amination or olefin aziridination. These unique heterocycles will engage in Ni-catalyzed cross-coupling reactions with aryl- and alkyl-Grignard reagents. Application of modern tools for C-N and C-C bond formation thus makes readily available functional amine derivatives and augments the possible uses for C-H amination in synthesis.

  DOI：

  10.1021/ol051896l
• 作为产物：
  描述：

  2-烯丙基酚 在 甲酸 、 氯磺酰异氰酸酯 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以78%的产率得到2-allylphenylsulfamate
  参考文献：
  名称：

  使用芳族氨基磺酸酯的手性二铑（II）催化的氮烯的不对称转移

  摘要：

  通过在PhI（OAc）2，MgO和手性Rh（II）催化剂存在下原位生成的苯基碘丁烷，已将芳香族氨基磺酸酯的对映体内和分子间插入活化的C–H键中。使用[Rh 2 {（S）-nttl} 4 ]和[Rh 2 {（R）-ntv} 4 ]作为具有最多52％ee的催化剂获得了最佳结果。相比之下，具有烯丙基邻位取代基的苯氨基磺酸盐则通过分子内的叠氮化而不是通过插入反应。当反应与过量的氨基磺酸盐一起进行时，茚满的分子间酰胺化以高达97％的产率进行。

  DOI：

  10.1016/j.tetasy.2004.01.015

文献信息

• Asymmetric transfer of nitrenes catalyzed by chiral dirhodium(II) using aromatic sulfamate esters
  作者：Corinne Fruit、Paul Müller

  DOI：10.1016/j.tetasy.2004.01.015

  日期：2004.3

  insertions of aromatic sulfamate esters into activated C–H bonds have been achieved via in situ generated phenyliodinanes in the presence of PhI(OAc)2, MgO, and chiral Rh(II) catalysts. The optimal results were obtained with [Rh2(S)-nttl}4] and [Rh2(R)-ntv}4] as catalysts with up to 52% ee. In contrast, phenylsulfamates with allylic ortho-substituents reacted via intramolecular aziridination rather

  通过在PhI（OAc）2，MgO和手性Rh（II）催化剂存在下原位生成的苯基碘丁烷，已将芳香族氨基磺酸酯的对映体内和分子间插入活化的C–H键中。使用[Rh 2 （S）-nttl} 4 ]和[Rh 2 （R）-ntv} 4 ]作为具有最多52％ee的催化剂获得了最佳结果。相比之下，具有烯丙基邻位取代基的苯氨基磺酸盐则通过分子内的叠氮化而不是通过插入反应。当反应与过量的氨基磺酸盐一起进行时，茚满的分子间酰胺化以高达97％的产率进行。
• Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-λ³-bromane Generated in Situ under Metal-Free Conditions
  作者：Md. Mahbubul Hoque、Kazunori Miyamoto、Norihiro Tada、Motoo Shiro、Masahito Ochiai

  DOI：10.1021/ol201868n

  日期：2011.10.21

  Ligand exchange of p-CF3C6H4BrF2 with acetoxy groups using AcOH and Ac2O affords (diacetoxybromo)benzene in a high yield, which undergoes azirldination of alkenes In the presence of TfNH2 and sulfamate esters in one pot under mild conditions. The azirldination with TfNH2 proceeds stereospecifically with retention of stereochemistry of olefins at room temperature using limiting amounts of olefins under transition-metal-free conditions. The one-pot aziridination procedure using sulfamate esters can be applied to the Intramolecular versions.
• JPS6233159A
  申请人：——

  公开号：JPS6233159A

  公开（公告）日：1987-02-13
• Exploring New Uses for C−H Amination:  Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates
  作者：Paul M. Wehn、J. Du Bois

  DOI：10.1021/ol051896l

  日期：2005.10.1

  Benzene-fused cyclic sulfamates are prepared from ortho-substituted phenolic starting materials through selective C-H amination or olefin aziridination. These unique heterocycles will engage in Ni-catalyzed cross-coupling reactions with aryl- and alkyl-Grignard reagents. Application of modern tools for C-N and C-C bond formation thus makes readily available functional amine derivatives and augments the possible uses for C-H amination in synthesis.
• Design and synthesis of cyclic sulfonamides and sulfamates as new calcium sensing receptor agonists
  作者：Lionel Kiefer、Tatiana Gorojankina、Philippe Dauban、Hélène Faure、Martial Ruat、Robert H. Dodd

  DOI：10.1016/j.bmcl.2010.10.006

  日期：2010.12

  The design, synthesis and calcimimetic properties of various cyclic sulfonamides and sulfamates are described. The latter were prepared from the corresponding o-alkenylarenesulfonamides via copper-or rhodium-catalyzed intramolecular aziridination. The size of the cyclic sulfonamide rings as well as the position of the crucial (R)-naphthylethylamine substituent significantly affected calcimimetic activity. The most active compounds were the six-and seven-membered sulfonamides 30a and 31a and sulfamate 34a. (C) 2010 Elsevier Ltd. All rights reserved.