N,N-dichloro-2-nitrobenzenesulfonamide | 52187-72-1

• 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: N,N-dichloro-2-nitrobenzenesulfonamide
• 英文别名: N,N-dichloro-o-nitrobenzenesulfonamide
• CAS: 52187-72-1
• 化学式: C₆H₄Cl₂N₂O₄S
• 分子量: 271.081
• InChiKey: RDMMHWFBTPMPDC-UHFFFAOYSA-N

物化性质

• 沸点：
  410.6±47.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dichloro-2-nitrobenzenesulfonamide 在 copper(I) trifluoromethanesulfonate benzene 、 2-NsNaH 、 sodium sulfite 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 anti methyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-phenylpropionate
  参考文献：
  名称：

  Copper-Catalyzed Aminohalogenation Using the 2-NsNCl₂/2-NsNHNa Combination as the Nitrogen and Halogen Sources for the Synthesis of anti-Alkyl 3-Chloro-2-(o-nitrobenzenesulfonamido)-3-arylpropionates

  摘要：

  [GRAPHICS]New regio- and stereoselective aminohalogenation of cinnamic esters has been developed using the combination of 5-NsNCl(2)/NsNHNa as the nitrogen and chlorine sources and copper(I) triflate as the catalyst. The new procedure provides an efficient synthesis of anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-phenylpropionate derivatives. Nine examples are presented with good yields (62-82%) and stereoselectivity ((5:1)-(30:)).

  DOI：

  10.1021/ol000120b
• 作为产物：
  描述：

  2-硝基苯磺酰胺 在 氯 、 三乙胺 作用下， 反应 3.0h， 以58%的产率得到N,N-dichloro-2-nitrobenzenesulfonamide
  参考文献：
  名称：

  摘要：

  Highly reactive N-(2,2,2-trichloroethylidene)nitrobenzenesulfonamides were synthesized by reaction of N,N-dichloronitrobenzenesulfonamides with trichloroethylene. Reactions of N-(2,2,2-trichlorocthylidene)nitrobenzenesulfonamides with oxygen and nitrogen nucleophiles gave products of addition at the double C=N bond; with arenes and haloarenes, the corresponding C-amidoalkylation products were obtained.

  DOI：

  10.1023/a:1012381602378

文献信息

• The combination of 2-NsNH2/NCS and MeCN as the nitrogen sources for the regio- and stereoselective formation of imidazolines from α,β-unsaturated ketones
  作者：Cody Timmons、Dianjun Chen、C. Elizabeth Barney、Sameer Kirtane、Guigen Li

  DOI：10.1016/j.tet.2004.10.022

  日期：2004.12

  A new nitrogen source combination was found for the regio- and stereoselective diamination of α,β-unsaturated ketones. This combination employs the readily available and inexpensive combination of NCS and 2-NsNH2 as the electrophilic nitrogen source, and acetonitrile as the nucleophilic nitrogen source, respectively. The reaction is easily performed by mixing olefin, 2-NsNH2, NCS and 4 Å molecular

  发现了一种新的氮源组合，用于α，β-不饱和酮的区域和立体选择性加氨基。该组合分别采用了NCS和2-NsNH 2作为亲电子氮源，而乙腈作为亲核氮源的容易获得且便宜的组合。在室温下，将烯烃，2-NsNH 2，NCS和4Å分子筛在新鲜蒸馏的乙腈中混合即可轻松进行反应。该反应是化学选择性的，没有形成任何卤胺副产物。建议存在一个由烯酮和2-NsNHCl形成的新的叠氮鎓离子，并通过[2 + 3]环加成机理与腈反应，该机理对所形成的加成产物具有极好的区域选择性和立体选择性。
• <i>N</i>,<i>N</i>-Dichloro-2-nitrobenzenesulfonamide as the Electrophilic Nitrogen Source for Direct Diamination of Enones
  作者：Wei Pei、Han-Xun Wei、Dianjun Chen、Allan D. Headley、Guigen Li

  DOI：10.1021/jo030193j

  日期：2003.10.1

  formations of 3-trichloromethyl and dichloromethyl imidazoline products (16 examples). The 2-Ns-protection group of the resulting diamine products can be easily cleaved under mild Fukuyama's conditions. A new mechanism hypothesis of [2+3] cyclization and N-chlorination has been proposed to explain the product structures, particularly their regio- and stereochemistry.

  N，N-二氯-邻-硝基苯磺酰胺（2-NsNCl2）被发现是一种有效的亲电子氮源，可直接使用不带任何金属催化剂的方法直接进行α，β-不饱和酮的氨化。该反应非常方便，无需保护惰性气体即可进行。发现分子筛（4 A）和温度在控制3-三氯甲基和二氯甲基咪唑啉产物的形成中起关键作用（16个实例）。在温和的福山条件下，所得二胺产物的2-Ns-保护基很容易裂解。已经提出了[2 + 3]环化和N-氯化的新机理假说来解释产物结构，特别是它们的区域和立体化学。
• Functionalization of α,β-Unsaturated Esters and Ketones:  A Facile and Highly Stereoselective One-Pot Approach to N-Protected α,β-Dehydroamino Acid Derivatives
  作者：Dianjun Chen、Li Guo、Junying Liu、Sameer Kirtane、John F. Cannon、Guigen Li

  DOI：10.1021/ol050002u

  日期：2005.3.1

  acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples. [reaction: see

  已经开发出一种针对α，β-脱氢氨基酸衍生物的新的，容易的且高度立体选择性的方案。通过使用α，β-不饱和酯和酮的氨基卤代反应，然后用特定的碱进行处理，一锅合成非常方便。发现仅两种[2.2.2]双环有机碱可有效用于该转化。对于12个实施例，获得了良好的产率（58-68％）和优异的Z-选择性。[反应：看文字]
• Recent Development of Regio‐ and Stereoselective Aminohalogenation Reaction of Alkenes
  作者：Guigen Li、S. R. S. Saibabu Kotti、Cody Timmons

  DOI：10.1002/ejoc.200600990

  日期：2007.6

  This microreview presents the development of the catalytic aminohalogenation of olefins. The olefin substrates include electron-deficient and functionalized ones, such as α,β-unsaturated esters, α,β-unsaturated ketones and α,β-unsaturated nitriles. In addition, the first asymmetric aminohalogenation by the use of Evans chiral auxiliaries is also discussed. The convincing evidence is provided to support

  这篇微观综述介绍了烯烃催化氨基卤化的发展。烯烃底物包括缺电子和功能化的底物，如α,β-不饱和酯、α,β-不饱和酮和α,β-不饱和腈。此外，还讨论了使用 Evans 手性助剂进行的第一次不对称氨基卤化。提供了令人信服的证据来支持氨基卤化反应的氮丙啶鎓机制。通过将邻位卤胺转化为其他重要的合成构件来描述该反应的应用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Ionic Liquid, 1-n-Butyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imide, Resulted in the First Catalyst-Free Aminohalogenation of Electron-Deficient Alkenes
  作者：Yi-Ning Wang、Bukuo Ni、Allan D. Headley、Guigen Li

  DOI：10.1002/adsc.200600277

  日期：2007.2.5

  The 2-Ns-based aminohalogenation of α,β-unsaturated ketones has been achieved in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide [bmim][N(SO2CF3)2]}. [Bmim][N(SO2CF3)2] was found to be superior not only to classical organic solvents but also to its counterpart, [bmim][BF4], which was proven to be successful in the TsNCl2-based aminohalogenation but failed to give

  α，β-不饱和酮的基于2-Ns的氨基卤化已在离子液体1 - n-丁基-3-甲基咪唑鎓双（三氟甲磺酰基）酰亚胺[bmim] [N（SO 2 CF 3）2 ]中实现}。发现[Bmim] [N（SO 2 CF 3）2 ]不仅优于经典有机溶剂，而且优于其对应物[bmim] [BF 4 ]，后者在基于TsNCl 2的基础上被证明是成功的氨基卤化反应，但未产生任何反应产物。本方法利用了2-NsNCl 2的优点。作为一锅操作中稳定的氮/卤素源而无需使用任何金属催化剂，无需特殊保护惰性气体即可方便地进行操作。检查了八个实例，这些实例具有良好至优异的立体选择性（1：5：一种异构体）和中等至良好的化学收率（53–72％）。