4-methoxy-N-(2-oxo-2-phenylethyl)benzenesulfonamide | 933025-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxy-N-(2-oxo-2-phenylethyl)benzenesulfonamide
• 英文别名: 4-methoxy-N-phenacylbenzenesulfonamide
• CAS: 933025-26-4
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: TXDLSOVTFWZIPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(2-oxo-2-phenylethyl)benzenesulfonamide 在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-amino-5-benzoyl-4-(3,4,5-trimethoxyphenyl)-1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  One-Pot Multicomponent Synthesis of Diversely Substituted 2-Aminopyrroles. A Short General Synthesis of Rigidins A, B, C, and D

  摘要：

  Privileged medicinal scaffolds based on the structures of tetra- and pentasubstituted 2-aminopyrroles were prepared via one-pot multicomponent reactions of structurally diverse aldehydes and N-(aryl-, hetaryl-, alkylsulfonamido)acetophenones with activated methylene compounds. This methodology was used in a four-step synthesis of alkaloids rigidins A, B, C, and Din overall yields of 61%, 58%, 60%, and 53%, respectively. Of these, rigidins B, C, and D were synthesized for the first time.

  DOI：

  10.1021/ol103149b
• 作为产物：
  描述：

  1-((4-methoxyphenyl)sulfonyl)-4-phenyl-1H-1,2,3-triazole 在 辛酸铑 、 水 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以98%的产率得到4-methoxy-N-(2-oxo-2-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles

  摘要：

  N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce alpha-amino ketones in high yield. An intermediary alpha-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

  DOI：

  10.1021/ja2104203

文献信息

• 2-Methylquinoline promoted oxidative ring-opening of N-sulfonyl aziridines with DMSO: facile synthesis of α-amino aryl ketones
  作者：Xianhui Zhang、Shuai-Shuai Li、Liang Wang、Lubin Xu、Jian Xiao、Zhen-Jiang Liu

  DOI：10.1016/j.tet.2016.10.041

  日期：2016.12

  2-Methylquinoline promoted room-temperature oxidative ring-opening of N-sulfonyl aziridines with DMSO has been developed, providing a mild and convenient method for the synthesis of a variety of different N-sulfonyl protected α-amino aryl ketones. The employment of 2-methylquinoline was crucial for the success of this mild transformation and good to excellent yields could be achieved.

  已经开发了2-甲基喹啉用DMSO促进N-磺酰基氮丙啶的室温氧化开环，为合成各种不同的N-磺酰基保护的α-氨基芳基酮提供了一种温和而便捷的方法。2-甲基喹啉的使用对于这种温和转化的成功至关重要，并且可以实现良好的优良收率。
• Base-Catalyzed NN Bond Cleavage of Hydrazones: Synthesis of α-Amino Ketones
  作者：Hai-Tao Tang、Yun-Bing Zhou、Yu Zhu、Hong-Chao Sun、Min Lin、Zhuang-Ping Zhan

  DOI：10.1002/asia.201400037

  日期：2014.5

  An efficient Cs2CO3‐promoted synthesis of α‐amino ketones using hydrazines, aldehydes, and α‐haloketones as starting materials through a cascade condensation/nucleophilic substitution/NN bond cleavage route is developed. The carbonyl group plays a key role in this novel NN bond cleavage process.

  通过级联缩合/亲核取代/ NN键裂解途径，以肼，醛和α-卤代酮为起始原料，开发了一种高效的Cs 2 CO 3促进的α-氨基酮合成方法。羰基在这种新颖的NN键裂解过程中起关键作用。
• Synthesis of 2-oxo-acetamidines via copper-catalyzed oxidative cross-coupling of α-amino ketone compounds with amines
  作者：Pengjie Wang、Yi Xiong、Yiqun Qin、Jiajia Zhang、Niannian Yi、Jiannan Xiang、Wei Deng

  DOI：10.1016/j.catcom.2019.105766

  日期：2019.11

  and efficient method for the synthesis of 2-oxo-acetamidines via copper-catalyzed oxidative cross-coupling of amines with α-amino ketone compounds was achieved. In this reaction, the C − N bond of α-amino ketone is broken and new C − N and CN bonds are constructed in one single transformation. This reaction system has a broad substrate scope and provides a facile pathway for the synthesis of 2-oxo-acetamidines

  用于经由铜的2-氧代acetamidines合成的一般和有效的方法-催化的氧化胺与α氨基酮化合物的交叉偶联物来实现的。在该反应中，α-氨基酮的C-N键断裂，并且通过一次转化即可构建新的C-N和C N键。该反应体系具有广泛的底物范围，并提供了合成2-氧代-乙acet的简便途径。
• Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines
  作者：Igor V. Magedov、Giovanni Luchetti、Nikolai M. Evdokimov、Madhuri Manpadi、Wim F.A. Steelant、Severine Van slambrouck、Paul Tongwa、Mikhail Yu. Antipin、Alexander Kornienko

  DOI：10.1016/j.bmcl.2008.01.019

  日期：2008.2

  Diversely substituted 2-pyrrolines have been prepared by a novel multicomponent process involving a reaction of various N-(aryl- and alkylsulfonamido)-acetophenones with aldehydes and malononitrile. While the reaction is highly regioselective, it is not stereoselective, generating a mixture of cis and trans 2-pyrrolines. A number of analogs from both cis and trans 2-pyrroline libraries were found to have antiproliferative activity in human cancer cell lines. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of <i>N</i>-Sulfonyl-1,2,3-triazoles
  作者：Tomoya Miura、Tsuneaki Biyajima、Tetsuji Fujii、Masahiro Murakami

  DOI：10.1021/ja2104203

  日期：2012.1.11

  N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce alpha-amino ketones in high yield. An intermediary alpha-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.