N-benzylidene-2-chlorobenzenamine oxide | 71013-75-7

• 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: N-benzylidene-2-chlorobenzenamine oxide
• 英文别名: N-(2-chlorophenyl)-α-phenylnitrone；α-phenyl-N-2-chlorophenylnitrone；N-(2-Chlorophenyl)(phenyl)methanimine N-oxide；N-(2-chlorophenyl)-1-phenylmethanimine oxide
• CAS: 71013-75-7
• 化学式: C₁₃H₁₀ClNO
• 分子量: 231.681
• InChiKey: MDAMGDYJLNAGFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzylidene-2-chlorobenzenamine oxide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以0.795 g的产率得到N-benzyl-N-(2-chlorophenyl)hydroxylamine
  参考文献：
  名称：

  Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and Cyclization Sequence

  摘要：

  Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N -> C-ortho trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.

  DOI：

  10.1021/jo401985h
• 作为产物：
  描述：

  2-氯苯基羟胺 、 苯甲醛 以 乙醇 为溶剂， 以to give α-phenyl-N-2-chlorophenylnitrone的产率得到N-benzylidene-2-chlorobenzenamine oxide
  参考文献：
  名称：

  Method of treating inflammation

  摘要：

  α-苯基-N-苯基亚硝基甲烷及其衍生物通过局部给药缓解炎症和相关疼痛和发热。

  公开号：

  US04197314A1

文献信息

• Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide
  作者：Abolfazl Hosseini、Peter R. Schreiner

  DOI：10.1021/acs.orglett.9b01192

  日期：2019.5.17

  A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.

  已经详细阐述了一种新的Kinugasa反应方案，用于利用电石和硝酮衍生物一锅合成4-取代的β-内酰胺。因此，在CuCl / NMI存在下，碳化钙被TBAF·3H 2 O活化。易于合成和使用廉价的化学药品，可快速获得仅在第4位被取代的实用数量的β-内酰胺。
• Highly Regio- and Stereoselective Dirhodium Vinylcarbene Induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/NO Cleavage and Rearrangement
  作者：Xiaochen Wang、Quentin M. Abrahams、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1002/anie.201201917

  日期：2012.6.11

  An abnormal cascade process provides a selective method for the preparation of tricyclic heterocycles. The cascade involves a metal carbene induced regioselective [3+2] cycloaddition, a Buchner reaction, and a [1,7]‐oxygen migration, which occurs with NO cleavage (see scheme). The products are formed with remarkable specificity.

  异常的级联过程提供了制备三环杂环的选择性方法。级联涉及诱导区域选择性[3 + 2]环加成的金属卡宾，布氏反应，和[1,7] -氧迁移，这与N-发生 ø裂解（参见方案）。产物具有明显的特异性。
• Asymmetric Synthesis of<i>trans</i>-β-Lactams by a Kinugasa Reaction on Water
  作者：Zhenling Chen、Lili Lin、Min Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.201204373

  日期：2013.6.3

  The asymmetric Kinugasa reaction was performed on pure water for the first time without the need for any organic co‐solvents. In contrast to most asymmetric Kinugasa reactions, trans‐β‐lactams were obtained as the major products in good yields, enantioselectivities, and diastereoselectivities (up to 90 % yield, 98 % ee, and >99:1 d.r.). This reaction is atom‐economical, environmentally friendly, and

  首次在纯水上进行不对称的Kinugasa反应，不需要任何有机助溶剂。与大多数不对称的Kinugasa反应相反，反式-β-内酰胺是主要产物，具有良好的收率，对映选择性和非对映选择性（最高90％收率，98％ee和> 99：1 dr）。该反应是原子经济的，环境友好的，并提供了合成有用但具有挑战性的产品。
• Method of treatment
  申请人：William H. Rorer, Inc.

  公开号：US04153722A1

  公开（公告）日：1979-05-08

  This invention describes a method of treating inflammation in warmblooded animals by topically administering an effective amount of .alpha.-phenyl-N-phenylnitrone and derivatives thereof.

  本发明描述了一种通过局部给予有效量的α-苯基-N-苯基硝基酮及其衍生物来治疗温血动物炎症的方法。
• Anti-inflammatory compositions containing .alpha.-phenyl-N-phenylnitrone
  申请人：William H. Rorer, Inc.

  公开号：US04224340A1

  公开（公告）日：1980-09-23

  This invention relates to novel compositions containing .alpha.-phenyl-n-phenylnitrone compounds which are useful for the topical treatment of inflammation in warm-blooded animals.

  本发明涉及一种新型组合物，其中包含对于温血动物的局部治疗炎症有用的α-苯基-N-苯基亚硝基化合物。