N,N-diethyl 4-bromophenyl O-sulfamate

• 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: N,N-diethyl 4-bromophenyl O-sulfamate
• 英文别名: (4-bromophenyl) N,N-diethylsulfamate
• 化学式: C₁₀H₁₄BrNO₃S
• 分子量: 308.196
• InChiKey: AGHCREDDYVRVLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-diethyl 4-bromophenyl O-sulfamate 在 正丁基锂 、 四甲基乙二胺 、 氘代甲醇 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成
  参考文献：
  名称：

  定向原位金属化方法。N，N-二烷基芳基邻氨基磺酸盐作为格氏试剂的新的定向金属化基团和交叉偶联伙伴。

  摘要：

  [反应：参见文本] 3的邻位金属化（RLi / THF / -93摄氏度），然后用各种亲电试剂淬火，构成了取代O-氨基磺酸芳基酯4a-k的新通用路线。O-氨基磺酸盐4e，4n-s和6a与Grignard试剂的Kumada-Corriu交叉偶联可得到联芳基9a-m，而Suzuki-Miyaura交叉使用2-halo和硼衍生物4h，4i和4k。苯并炔的偶合和生成导致萘酚7a和7b。报告了OSONEt（2）的相对金属化等级。

  DOI：

  10.1021/ol050393c
• 作为产物：
  描述：

  4-溴苯酚 在 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 N,N-diethyl 4-bromophenyl O-sulfamate
  参考文献：
  名称：

  O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release

  摘要：

  Sequential replacement of imidazole from sulfonyldiimidazole by phenols and then amines leads to O-arylsulfamate esters. Application of this coupling method to 19 phenols and 6 amines generates a library of 114 sulfamate esters, Ar-OSO2-NR2. A sulfamate based conjugate of ethinyl estradiol was prepared by using the steroid 3-hydroxyl as the phenol component, and an amino amide derived from linoleic acid as the amine. Hydrolysis of this conjugate was studied in aqueous buffer at pH values 2, 5, and 7.4, and (essentially identical) respective half-lives of 6.8, 6.6, and 6.7 days were observed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.065

文献信息

• A new synthetic route to aryl hydroxysulfonamides via a novel Fries-type rearrangement of aryl N,N-dialkylsulfamates
  作者：G.Anthony Benson、Patrick J Maughan、Declan P Shelly、William J Spillane

  DOI：10.1016/s0040-4039(01)01893-7

  日期：2001.12

  A novel thia-Fries rearrangement of sulfamates 1 in AlCl3 giving good yields of para-2 and ortho-3 arylhydroxysulfonamides offers a new and efficient route to these sulfonamides.

  一种新型硫杂Fries重排氨基磺酸盐的1中的AlCl 3给出良好产率的对- 2和邻- 3个arylhydroxysulfonamides要约这些磺胺一种新的和有效的途径。
• O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release
  作者：Baocheng Yang、Zhexun Sun、Changzhi Liu、Yan Cui、Zhilei Guo、Yuwei Ren、Zhijian Lu、Spencer Knapp

  DOI：10.1016/j.tetlet.2014.10.065

  日期：2014.12

  Sequential replacement of imidazole from sulfonyldiimidazole by phenols and then amines leads to O-arylsulfamate esters. Application of this coupling method to 19 phenols and 6 amines generates a library of 114 sulfamate esters, Ar-OSO2-NR2. A sulfamate based conjugate of ethinyl estradiol was prepared by using the steroid 3-hydroxyl as the phenol component, and an amino amide derived from linoleic acid as the amine. Hydrolysis of this conjugate was studied in aqueous buffer at pH values 2, 5, and 7.4, and (essentially identical) respective half-lives of 6.8, 6.6, and 6.7 days were observed. (C) 2014 Elsevier Ltd. All rights reserved.
• Directed Ortho Metalation Methodology. The <i>N</i>,<i>N</i>-Dialkyl Aryl <i>O</i>-Sulfamate as a New Directed Metalation Group and Cross-Coupling Partner for Grignard Reagents
  作者：Todd K. Macklin、Victor Snieckus

  DOI：10.1021/ol050393c

  日期：2005.6.1

  with a variety of electrophiles constitutes a new general route to substituted aryl O-sulfamates 4a-k. The Kumada-Corriu cross-coupling of O-sulfamates 4e, 4n-s, and 6a with Grignard reagents gives biaryls 9a-m, and the use of 2-halo and boron derivatives 4h, 4i, and 4k for Suzuki-Miyaura cross-coupling and generation of benzynes leads to naphthols 7a and 7b. A relative metalation ranking of the OSONEt(2)

  [反应：参见文本] 3的邻位金属化（RLi / THF / -93摄氏度），然后用各种亲电试剂淬火，构成了取代O-氨基磺酸芳基酯4a-k的新通用路线。O-氨基磺酸盐4e，4n-s和6a与Grignard试剂的Kumada-Corriu交叉偶联可得到联芳基9a-m，而Suzuki-Miyaura交叉使用2-halo和硼衍生物4h，4i和4k。苯并炔的偶合和生成导致萘酚7a和7b。报告了OSONEt（2）的相对金属化等级。