(E)-methyl 2-((phenylamino)methyl)-3-(p-tolyl)acrylate | 786669-28-1

• 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: (E)-methyl 2-((phenylamino)methyl)-3-(p-tolyl)acrylate
• 英文别名: methyl (E)-2-(anilinomethyl)-3-(4-methylphenyl)prop-2-enoate
• CAS: 786669-28-1
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: YWWKOGKGOVVYBU-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-((phenylamino)methyl)-3-(p-tolyl)acrylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (E)-2-(anilinomethyl)-3-(4-methylphenyl)prop-2-enoic acid
  参考文献：
  名称：

  Synthesis of 4b,5,10a,11-tetrahydroindeno[1,2-b]quinolin-10-ones from Baylis–Hillman adducts

  摘要：

  We developed an efficient synthetic method for indenoquinoline skeletons from Baylis-Hillman adducts. 4b,5,10a,11-Tetrahydroindeno[1,2-b]quinolin-10-ones and 7H-indeno[2,1-c]quinolines were prepared from Baylis-Hillman adducts in polyphosphoric acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.075
• 作为产物：
  描述：

  2-(羟基对甲苯甲基)-丙烯酸甲酯 在 硫酸 、 potassium carbonate 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (E)-methyl 2-((phenylamino)methyl)-3-(p-tolyl)acrylate
  参考文献：
  名称：

  以2,2,6,6-四甲基哌啶-N-氧基（TEMPO）为氧化剂的烯丙基胺的氧化Heck偶联制备四取代的烯烃

  摘要：

  AbstractThe paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) is used and coupling reactions occur under very mild conditions at room temperature. The densely substituted alkenes are formed in good to excellent yields with complete control of the diastereoselectivity. Substrate scope with respect to the allylic amine and the arylboronic acid is investigated.magnified image

  DOI：

  10.1002/adsc.201300846

文献信息

• A Simple and Direct Synthesis of 3-Methylene-1, 4-diarylazetidin-2-ones and (E)-3-Arylidene-1-phenylazetidin-2-ones Using Baylis–Hillman Derivatives
  作者：Manickam Bakthadoss、Jayakumar Srinivasan、Raman Selvakumar

  DOI：10.1071/ch13382

  日期：——

  Herein we describe a direct method, promoted by potassium tert-butoxide (KOtBu), for the synthesis of highly substituted α-methylene β-lactams and α-arylidene β-lactams from the amino ester intermediates derived from the acetates and bromo derivatives of the Baylis–Hillman adducts. A variety of β-lactams was synthesized in a single step with good yields.

  在此，我们介绍了一种在叔丁醇钾（KOtBu）促进下直接合成高取代的 α-亚甲基 β-内酰胺和 α-亚芳基 β-内酰胺的方法，其氨基酯中间体来自 Baylis-Hillman 加合物的乙酸盐和溴衍生物。各种 β-内酰胺都是一步合成的，而且收率很高。
• Synthesis of 4b,5,10a,11-tetrahydroindeno[1,2-b]quinolin-10-ones from Baylis–Hillman adducts
  作者：Chang Gon Lee、Ka Young Lee、Saravanan GowriSankar、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2004.08.075

  日期：2004.9

  We developed an efficient synthetic method for indenoquinoline skeletons from Baylis-Hillman adducts. 4b,5,10a,11-Tetrahydroindeno[1,2-b]quinolin-10-ones and 7H-indeno[2,1-c]quinolines were prepared from Baylis-Hillman adducts in polyphosphoric acid. (C) 2004 Elsevier Ltd. All rights reserved.
• Oxidative Heck Coupling of Allylic Amines with 2,2,6,6‐Tetramethylpiperidine‐ <i>N</i> ‐oxyl (TEMPO) as Oxidant for the Preparation of Tetrasubstituted Alkenes
  作者：Zhiheng He、Birgit Wibbeling、Armido Studer

  DOI：10.1002/adsc.201300846

  日期：2013.12.16

  AbstractThe paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) is used and coupling reactions occur under very mild conditions at room temperature. The densely substituted alkenes are formed in good to excellent yields with complete control of the diastereoselectivity. Substrate scope with respect to the allylic amine and the arylboronic acid is investigated.magnified image