(3-Phenylbute-3-enethioyl)morpholine | 62825-30-3

• 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-Phenylbute-3-enethioyl)morpholine
• 英文别名: N-morpholinocinnamthioamide；(E)-1-morpholino-3-phenylprop-2-ene-1-thione；(E)-1-morpholin-4-yl-3-phenylprop-2-ene-1-thione
• CAS: 62825-30-3
• 化学式: C₁₃H₁₅NOS
• 分子量: 233.334
• InChiKey: MXAHZYYGHOCIDG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-Phenylbute-3-enethioyl)morpholine 在 sodium hydroxide 作用下， 反应 0.02h， 生成 肉桂酸
  参考文献：
  名称：

  MICROWAVE-ASSISTED RAPID HYDROLYSIS AND PREPARATION OF THIOAMIDES BY WILLGERODT-KINDLER REACTION

  摘要：

  Aldehydes and aryl alkyl ketones were efficiently transformed to thioamides with the same number of carbon atoms via Willgerodt-Kindler reaction under microwave irradiation in solvent-free conditions. The thioamides obtained were hydrolyzed to corresponding carboxylic acids with microwave dielectric heating in one minute. Both reactions are very fast and the yields are excellent.

  DOI：

  10.1081/scc-100000216
• 作为产物：
  描述：

  3-hydroxy-1-morpholino-3-phenylpropan-1-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以86%的产率得到(3-Phenylbute-3-enethioyl)morpholine
  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

文献信息

• Cooperative Activation of Alkyne and Thioamide Functionalities; Direct Catalytic Asymmetric Conjugate Addition of Terminal Alkynes to α,β-Unsaturated Thioamides
  作者：Ryo Yazaki、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1002/asia.201100050

  日期：2011.7.4

  revealed that the intermediate copper‐thioamide enolate functioned as a Brønsted base to generate copper alkynylide from the terminal alkyne, thus driving the catalytic cycle through an efficient proton transfer between substrates. These findings led to the identification of a more convenient catalyst using potassium hexamethyldisilazane (KHMDS) as the Brønsted base, which was particularly effective for

  详细描述了将末端炔烃直接催化不对称共轭加成至α，β-不饱和硫代酰胺的详细研究。一种柔软的路易斯酸/硬布朗斯台德碱协同催化剂，包含[Cu（CH 3 CN）4 ] PF 6，双膦配体和Li（OC 6 H 4 - p‐OMe）同时激活两种底物以补偿炔烃铜的低反应性。一系列控制实验表明，中间体铜硫代酰胺醇烯酸酯起布朗斯台德碱的作用，从末端炔烃生成炔烃铜，从而通过底物之间的有效质子转移驱动催化循环。这些发现导致鉴定了使用六甲基二硅氮烷钾（KHMDS）作为布朗斯台德碱的更方便的催化剂，该催化剂对于甲硅烷基乙炔的反应特别有效。硫酰胺官能团的不同转化以及GPR40受体激动剂AMG-837的简洁对映选择性合成突出了本催化方法的合成用途。
• Otten, P. A.; Gen, A. van der, Recueil des Travaux Chimiques des Pays-Bas, 1994, vol. 113, # 11, p. 499 - 506
  作者：Otten, P. A.、Gen, A. van der

  DOI：——

  日期：——