4-(Dimethylamino)phenyl dimethylsulfamate | 1201594-38-8

• 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: 4-(Dimethylamino)phenyl dimethylsulfamate
• 英文别名: [4-(dimethylamino)phenyl] N,N-dimethylsulfamate
• CAS: 1201594-38-8
• 化学式: C₁₀H₁₆N₂O₃S
• 分子量: 244.315
• InChiKey: JNIACOOFQULNIB-UHFFFAOYSA-N

物化性质

• 沸点：
  356.5±44.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(Dimethylamino)phenyl dimethylsulfamate 、 chlorozinc(1+),methoxybenzene 在 1-甲基吡咯烷 、 C₂₀H₂₀ClN₃Ni 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以81%的产率得到4'-甲氧基-N,N-二甲基联苯-4-胺
  参考文献：
  名称：

  芳基氨基磺酸盐与芳基氯化锌的钳-镍催化交叉偶联

  摘要：

  镍 N,N,N-钳形配合物 2 被证明可以在温和条件下有效催化芳基氨基磺酸酯与芳基氯化锌的交叉偶联。该反应适用于广泛的底物，并耐受各种官能团。

  DOI：

  10.1002/ejoc.201500987
• 作为产物：
  描述：

  4-二甲氨基苯酚 、 二甲胺基磺酰氯 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 11.17h， 以89%的产率得到4-(Dimethylamino)phenyl dimethylsulfamate
  参考文献：
  名称：

  Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates

  摘要：

  The first Suzuki-Miyaura cross-couplings of carbamates, carbonates, and sulfamates is described. The method provides a powerful means of using simple derivatives of phenol as precursors to polysubstituted aromatic compounds, as exemplified by a concise synthesis of the anti-inflammatory drug flurbiprofen.

  DOI：

  10.1021/ja906477r

文献信息

• Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates
  作者：Xiaofeng Yu、Zhen Zhang、Renyuan Song、Liping Gou、Guangrong Wang

  DOI：10.1515/hc-2020-0001

  日期：2020.2.28

  2-Aryl-benzothiazoles have been successfully synthesized via a simple coupling reaction between benzothiazoles and aryl sulfamates using a nickel catalyst. The nickel catalyst is inexpensive, reusable and commercially available. In addition, the use of highly expensive palladium catalysts and unstable raw materials has been avoided. 2-Aryl-benzothiazoles bearing various substituents on the aryl groups were obtained in good yield.

  摘要：使用镍催化剂，通过苯并噻唑和芳基磺酸酯的简单偶联反应成功合成了2-芳基苯并噻唑。镍催化剂价格便宜，可重复使用且商业上可获得。此外，避免了使用高昂的钯催化剂和不稳定的原材料。得到了带有不同取代基的芳基苯并噻唑，收率良好。
• Suzuki−Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies
  作者：Kyle W. Quasdorf、Aurora Antoft-Finch、Peng Liu、Amanda L. Silberstein、Anna Komaromi、Tom Blackburn、Stephen D. Ramgren、K. N. Houk、Victor Snieckus、Neil K. Garg

  DOI：10.1021/ja200398c

  日期：2011.4.27

  The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl2(PCy3)(2) to furnish biaryls in good to excellent yields. A broad scope for this methodology has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodology in the synthesis of polysubstituted aromatic compounds of natural product and bioactive molecule interest.
• US8546607B2
  申请人：——

  公开号：US8546607B2

  公开（公告）日：2013-10-01
• Pincer-Nickel-Catalyzed Cross-Coupling of Aryl Sulfamates with Arylzinc Chlorides
  作者：Jian-Long Tao、Zhong-Xia Wang

  DOI：10.1002/ejoc.201500987

  日期：2015.9

  The nickel N,N,N-pincer complex 2 was demonstrated to effectively catalyze the cross-coupling of aryl sulfamates with arylzinc chlorides under mild conditions. The reaction is suitable for a wide range of substrates, and tolerates various functional groups.

  镍 N,N,N-钳形配合物 2 被证明可以在温和条件下有效催化芳基氨基磺酸酯与芳基氯化锌的交叉偶联。该反应适用于广泛的底物，并耐受各种官能团。
• Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates
  作者：Kyle W. Quasdorf、Michelle Riener、Krastina V. Petrova、Neil K. Garg

  DOI：10.1021/ja906477r

  日期：2009.12.16

  The first Suzuki-Miyaura cross-couplings of carbamates, carbonates, and sulfamates is described. The method provides a powerful means of using simple derivatives of phenol as precursors to polysubstituted aromatic compounds, as exemplified by a concise synthesis of the anti-inflammatory drug flurbiprofen.