methyl (2E)-3-(4-chlorophenyl)-2-[(toluene-4-sulfonylamino)methyl]acrylate | 481054-91-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2E)-3-(4-chlorophenyl)-2-[(toluene-4-sulfonylamino)methyl]acrylate
• 英文别名: methyl (E)-3-(4-chlorophenyl)-2-[[(4-methylphenyl)sulfonylamino]methyl]prop-2-enoate
• CAS: 481054-91-5
• 化学式: C₁₈H₁₈ClNO₄S
• 分子量: 379.864
• InChiKey: PTZFRIVYHQRAAX-RVDMUPIBSA-N

物化性质

• 沸点：
  548.9±60.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-(4-chlorophenyl)-2-[(toluene-4-sulfonylamino)methyl]acrylate 在 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 methyl 4-(4-chlorophenyl)-5-methylnicotinate
  参考文献：
  名称：

  钯催化的多米诺环化（5-exo / 3-exo），通过钯重排进行环扩环和芳构化：由森田-贝利斯-希尔曼加合物合成4-芳基烟酸酯

  摘要：

  通过N-（2-溴代烯丙基）-N-肉桂基甲苯磺酰胺的钯催化级联反应以高收率合成了各种4-芳基烟酸酯衍生物。该反应涉及多米诺骨牌5 exo / 3 exo碳钯，通过钯重排进行的扩环，以及芳构化过程。

  DOI：

  10.1002/adsc.201300211
• 作为产物：
  描述：

  methyl 2-[(4-chlorophenyl)-(toluene-4-sulfonylamino)methyl]acrylate 在 四丁基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以76%的产率得到methyl (2E)-3-(4-chlorophenyl)-2-[(toluene-4-sulfonylamino)methyl]acrylate
  参考文献：
  名称：

  Highly Efficient aza-Baylis−Hillman Reaction of N-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds

  摘要：

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.

  DOI：

  10.1021/jo035103p

文献信息

• Utility of Allylic Azides for the Synthesis of Fused Triazoles and Tetrazoles via Intramolecular Cycloaddition¹
  作者：Sanjay Batra、Amita Mishra、Samiran Hutait、Subhendu Bhowmik、Neeraj Rastogi、Raja Roy

  DOI：10.1055/s-0029-1218847

  日期：2010.8

  The synthesis of a variety of annulated triazoles and tetrazoles from differently substituted allyl azides, afforded from the Baylis-Hillman adduct of acrylates, using intramolecular cycloaddition approach is described. Baylis-Hillman - allyl azide - cycloaddition - triazole - tetrazole This is CDRI communication No. 7938.

  描述了使用分子内环加成法由丙烯酸酯的Baylis-Hillman加合物提供的，由不同取代的烯丙基叠氮化物合成各种环状三唑和四唑的方法。 Baylis-Hillman-烯丙基叠氮化物-环加成-三唑-四唑 这是CDRI通讯7938。
• Synthesis of quinolines from the Baylis–Hillman acetates via the oxidative cyclization of sulfonamidyl radical as the key step
  作者：Jae Nyoung Kim、Yun Mi Chung、Yang Jin Im

  DOI：10.1016/s0040-4039(02)01314-x

  日期：2002.8

  Ethyl 3-quinolinecarboxylates 5 were synthesized in good to moderate yields from the Baylis-Hillman acetates 1 via the oxidative cyclization reaction of the N-tosylamidyl radical, which was generated from the rearranged tosylamide derivatives 2 by iodobenzene diacetate and iodine. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Highly Efficient aza-Baylis−Hillman Reaction of <i>N</i>-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds
  作者：Yong-Mei Xu、Min Shi

  DOI：10.1021/jo035103p

  日期：2004.1.1

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.
• Palladium-Catalyzed Domino Cyclization (5-<i>exo</i>/3-<i>exo</i>), Ring- Expansion by Palladium Rearrangement, and Aromatization: An Expedient Synthesis of 4-Arylnicotinates from Morita-Baylis-Hillman Adducts
  作者：Ko Hoon Kim、Se Hee Kim、Hyun Ju Lee、Jae Nyoung Kim

  DOI：10.1002/adsc.201300211

  日期：2013.7.8

  Various 4‐arylnicotinate derivatives were synthesized via a palladium‐catalyzed cascade reaction of N‐(2‐bromoallyl)‐N‐cinnamyltosylamides in a one‐pot procedure in good yields. The reaction involves a domino 5‐exo/3‐exo carbopalladation, ring‐expansion by palladium rearrangement, and an aromatization process.

  通过N-（2-溴代烯丙基）-N-肉桂基甲苯磺酰胺的钯催化级联反应以高收率合成了各种4-芳基烟酸酯衍生物。该反应涉及多米诺骨牌5 exo / 3 exo碳钯，通过钯重排进行的扩环，以及芳构化过程。