4-hydroxy-N,4-diphenylbutanamide | 119690-92-5

• 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: 4-hydroxy-N,4-diphenylbutanamide
• CAS: 119690-92-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: JHVGOKUJRUWXAX-UHFFFAOYSA-N

物化性质

• 沸点：
  504.4±43.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-N,4-diphenylbutanamide 在 potassium tert-butylate 、 对甲苯磺酰氯 作用下， 生成 1,5-二苯基吡咯烷-2-酮
  参考文献：
  名称：

  Takahata, Hiroki; Wang, Eng-Chi; Yamazaki, Takao, Synthetic Communications, 1988, vol. 18, # 10, p. 1159 - 1166

  摘要：

  DOI：
• 作为产物：
  描述：

  N-phenyl 3-benzoylpropionamide 在 C₅₀H₅₂Cl₂O₄P₂Ru*C₁₉H₂₆N₂O₂ 、 potassium tert-butylate 、 氢气 作用下， 以 异丙醇 为溶剂， 30.0 ℃ 、1.01 MPa 条件下， 反应 15.0h， 以97%的产率得到4-hydroxy-N,4-diphenylbutanamide
  参考文献：
  名称：

  Enantioselective Ruthenium(II)/Xyl-SunPhos/Daipen-Catalyzed Hydrogenation of γ-Ketoamides

  摘要：

  A series of gamma-hydroxy amides were synthesized with high enantioselectivities (up to 99%) using asymmetric hydrogenation of the corresponding gamma-ketoamides in the presence of Ru-Xyl-SunPhos-Daipen catalyst providing key building blocks for a variety of naturally occurring and biologically active compounds.

  DOI：

  10.1021/jo5008916

文献信息

• Metal‐Free Synthesis of <i>N</i> ‐Aryl Amides using Organocatalytic Ring‐Opening Aminolysis of Lactones
  作者：Wusheng Guo、José Enrique Gómez、Luis Martínez‐Rodríguez、Nuno A. G. Bandeira、Carles Bo、Arjan W. Kleij

  DOI：10.1002/cssc.201700415

  日期：2017.5.9

  Catalytic ring‐opening of bio‐sourced non‐strained lactones with aromatic amines can offer a straightforward, 100 % atom‐economical, and sustainable pathway towards relevant N‐aryl amide scaffolds. Herein, the first general, metal‐free, and highly efficient N‐aryl amide formation is reported from poorly reactive aromatic amines and non‐strained lactones under mild operating conditions using an organic

  生物来源的非应变内酯与芳族胺的催化开环可以提供一种直接的，100％原子经济且可持续的通往相关N芳基酰胺支架的途径。在此，据报道，在温和的操作条件下，使用有机双环胍催化剂，由反应性较差的芳族胺和非应变的内酯首次形成了无金属且高效的N-芳基酰胺。该协议具有很高的应用潜力，例如与药物相关的分子的形式合成。
• Sulfur-containing heterocycles derived by the reaction of hydroxy-amides and Lawesson's reagent
  作者：Takehiko Nishio

  DOI：10.1016/0040-4039(95)01232-7

  日期：1995.8

  A simple one-pot reaction between hydroxy-amides (1) located, 1,3- or 1,4- to each other, and Lawesson's reagent (LR) gives sulfur-containg heterocycles such as tetrahydrothiophene-2-imines (4), tetrahydrothiophene-2-thione (5) and tetrahydrothiopyrandash2-thione (6). Similar reaction of 3-N-acylamino-alcohols (7) affords thiazoline derivatives (9).

  彼此之间存在1,3-或1,4-的羟基酰胺（1）与Lawesson试剂（LR）之间的简单一锅反应，得到了含硫杂环，如四氢噻吩-2-亚胺（4），四氢噻吩-2-硫酮（5）和四氢噻吩并ash2-硫酮（6）。3-N-酰基氨基醇的类似反应（7）得到噻唑啉衍生物（9）。
• 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.
• TAKAHATA, HIROKI;WANG, ENG-CHI;YAMAZAKI, TAKAO, SYNTH. COMMUN., 18,(1988) N 10, C. 1159-1165
  作者：TAKAHATA, HIROKI、WANG, ENG-CHI、YAMAZAKI, TAKAO

  DOI：——

  日期：——
• Enantioselective Ruthenium(II)/Xyl-SunPhos/Daipen-Catalyzed Hydrogenation of γ-Ketoamides
  作者：Mengmeng Zhao、Wanfang Li、Xiaoming Li、Kai Ren、Xiaoming Tao、Xiaomin Xie、Tahar Ayad、Virginie Ratovelomanana-Vidal、Zhaoguo Zhang

  DOI：10.1021/jo5008916

  日期：2014.7.3

  A series of gamma-hydroxy amides were synthesized with high enantioselectivities (up to 99%) using asymmetric hydrogenation of the corresponding gamma-ketoamides in the presence of Ru-Xyl-SunPhos-Daipen catalyst providing key building blocks for a variety of naturally occurring and biologically active compounds.