3-hydroxy-N-methyl-N-phenyl-3-phenylpropanamide | 52190-16-6

• 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: 3-hydroxy-N-methyl-N-phenyl-3-phenylpropanamide
• 英文别名: 3-hydroxy-N-methyl-N,3-diphenylpropanamide；3-hydroxy-3-phenyl-propionic acid-(N-methyl-anilide)；3-Hydroxy-3-phenyl-propionsaeure-(N-methyl-anilid)
• CAS: 52190-16-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: UHQKNMYZMRQTDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-N-methyl-N-phenyl-3-phenylpropanamide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以77%的产率得到N-methyl-N-phenylcinnamthioamide
  参考文献：
  名称：

  Thionation of ω-hydroxy amides with Lawesson's reagent: Synthesis of thioenamides and sulfur-containing heterocycles

  摘要：

  The thionation of omega-hydroxy amides with Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)- 1,3,2,4-dithiaphosphetane-2,4-disulfide] is described. The treatment of 3-hydroxy amides 1 with LR exclusively gave thioenamides 2 in fair yields. The treatment of 4-hydroxy amides 5 with LR yielded sulfur-containing heterocycles such as tetrahydrothiophene-2-imines 6 and tetrahydrothiophene-2-thione 7a through cyclization of intermediates, 4-mercapto amides 8. The 5-hydroxy amides 13 also reacted with LR to afford tetrahydrothiopyrane-2-thione 14 as the the sole product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00200-8
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-hydroxy-N-methyl-N-phenyl-3-phenylpropanamide
  参考文献：
  名称：

  一锅烯醇硅烷形成-Mukaiyama Aldol反应：交叉的醛-醛偶联，硫代酯底物和酯溶剂中的反应

  摘要：

  三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）和三烷基胺碱可在单个反应瓶中促进原位烯醇硅烷/甲硅烷基烯酮缩醛的形成和Mukaiyama aldol加成反应。不需要分离所需的烯醇硅烷或甲硅烷基烯酮缩醛。例如，α-二取代的醛与不可烯化的醛之间的交叉醇醛缩合反应以良好的产率产生β-羟基醛。在相关的反应中，普通的实验室溶剂乙酸乙酯既充当烯醇化物前体又充当绿色反应溶剂。当使用硫酯作为烯醇化物前体时，常规观察到高产率地加成到不可烯化的醛中。

  DOI：

  10.1016/j.tetlet.2019.151192

文献信息

• Extension of the Reformatsky Reaction to new Types of Compounds
  作者：Reynold C. Fuson、Norman. Thomas

  DOI：10.1021/jo50018a022

  日期：1953.12.1
• Wakita, Yoshiaki; Kobayashi, Toshio; Maeda, Minoru, Chemical and pharmaceutical bulletin, 1982, vol. 30, p. 3395 - 3398
  作者：Wakita, Yoshiaki、Kobayashi, Toshio、Maeda, Minoru、Kojima, Masaharu

  DOI：——

  日期：——
• WAKITA, YOSHIAKI;KOBAYASHI, TOSHIO;MAEDA, MINORU;KOJIMA, MASAHARU, CHEM. AND PHARM. BULL., 1982, 30, N 9, 3395-3396
  作者：WAKITA, YOSHIAKI、KOBAYASHI, TOSHIO、MAEDA, MINORU、KOJIMA, MASAHARU

  DOI：——

  日期：——
• One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents
  作者：C. Wade Downey、Grant J. Dixon、Jared A. Ingersoll、Claire N. Fuller、Kenneth W. MacCormac、Anna Takashima、Rohina Sediqui

  DOI：10.1016/j.tetlet.2019.151192

  日期：2019.10

  Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable

  三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）和三烷基胺碱可在单个反应瓶中促进原位烯醇硅烷/甲硅烷基烯酮缩醛的形成和Mukaiyama aldol加成反应。不需要分离所需的烯醇硅烷或甲硅烷基烯酮缩醛。例如，α-二取代的醛与不可烯化的醛之间的交叉醇醛缩合反应以良好的产率产生β-羟基醛。在相关的反应中，普通的实验室溶剂乙酸乙酯既充当烯醇化物前体又充当绿色反应溶剂。当使用硫酯作为烯醇化物前体时，常规观察到高产率地加成到不可烯化的醛中。
• Thionation of ω-hydroxy amides with Lawesson's reagent: Synthesis of thioenamides and sulfur-containing heterocycles
  作者：Takehiko Nishio、Hiroshi Sekiguchi

  DOI：10.1016/s0040-4020(99)00200-8

  日期：1999.4

  The thionation of omega-hydroxy amides with Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)- 1,3,2,4-dithiaphosphetane-2,4-disulfide] is described. The treatment of 3-hydroxy amides 1 with LR exclusively gave thioenamides 2 in fair yields. The treatment of 4-hydroxy amides 5 with LR yielded sulfur-containing heterocycles such as tetrahydrothiophene-2-imines 6 and tetrahydrothiophene-2-thione 7a through cyclization of intermediates, 4-mercapto amides 8. The 5-hydroxy amides 13 also reacted with LR to afford tetrahydrothiopyrane-2-thione 14 as the the sole product. (C) 1999 Elsevier Science Ltd. All rights reserved.