N-<(R)-1-phenethyl>thiobenzamide | 86022-50-6

• 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: N-<(R)-1-phenethyl>thiobenzamide
• 英文别名: N-<(R)-1-Phenylethyl>thiobenzamide；(R)-N-(1-phenylethyl)benzothioamide；N-[(1R)-1-phenylethyl]benzenecarbothioamide
• CAS: 86022-50-6
• 化学式: C₁₅H₁₅NS
• 分子量: 241.357
• InChiKey: LCUFGDBHLKLNJM-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-<(R)-1-phenethyl>thiobenzamide 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.08h， 生成 (1R,4R,5S)-4,5-Dimethyl-1-phenyl-2-<(R)-1-phenylethyl>-6-thia-2-azabicyclo<2.2.0>hexan-3-one
  参考文献：
  名称：

  Solid-State Photochemistry: Diastereoselective Synthesis of Thietane-Fused .beta.-Lactams from an Acyclic Monothioimide with a Chiral Group

  摘要：

  Irradiation of N-[(R)-1-phenylethyl]-N-tigloythiobenzamide in benzene solution resulted in both [2 + 2] thietane and thioketone formation reactions (via beta-hydrogen abstraction by the thiocarbonyl sulfur). Diastereoselectivity in the thietane formation was not observed, in that four beta-lactams were obtained in similar yields. In contrast to the solution photochemistry, irradiation of the crystals provided remarkably high diastereoselectivities. At 15 degrees C, de of the syn-beta-lactams was 61% and the ratio of syn/anti was to 8.7 (chemical yield: 78%). The solid-state photoreaction proceeded even at -78 degrees C, with higher diastereoselectivity. At low conversion (9%), only syn isomers (de = 93%) were obtained, and 71% de was observed even at 90% conversion. An X-ray crystal structure analysis of the monothioimide indicates that the crystal is orthorhombic, of space group P2(1)2(1)2(1), and the distances between the sulfur atom and the alkenyl carbon, and from the thiocarbonyl carbon to the alkenyl carbon, are 4.29 and 3.00 Angstrom, respectively. The twist angle tau of the C(=O)-N bond is 40.8 degrees and that of the C(=S)-N bond is 19.9 degrees. On the other hand, the sulfur atom and abstractable hydrogen atom are in close proximity, and the value for d is 2.40 Angstrom, for theta is 127.3 degrees, for Delta is 67.9 degrees, and for omega is 6.2 degrees. From these values, it is apparent that this reactant is well-positioned for hydrogen transfer in the crystalline state.

  DOI：

  10.1021/jo00090a034
• 作为产物：
  描述：

  (R)-(+)-N-苯甲酰-Alpha-甲基苯胺 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以77%的产率得到N-<(R)-1-phenethyl>thiobenzamide
  参考文献：
  名称：

  Optically active transition metal complexes 111. Synthesis and structure of a new thioamidato rhodium(I) complex

  摘要：

  The reaction of [Rh(cod)Cl](2) with deprotonated N-[(A)-1-phenylethyl]thiobenzamide affords the new complex 1. In the solid state 1 exists as a binuclear complex with the two sulfur atoms of two thioamidato ligands bridging the Rh atoms. The molecular structure of 1 was determined by X-ray analysis: C46H52N2S2Rh2, monoclinic, space group C2, a - 10.564(4), b = 16.864(5), c = 23.548(7), beta = 95.05(3)degrees, Z = 2 x 2, R = 0.046, R(w) = 0,039. Complex 1 equilibrates with an isomer in solution at room temperature. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00406-5

文献信息

• Europhtal: An industrial cobalt phthalocyanine complex as the efficient catalyst for synthesis of thioamides by one‐pot reaction of mercaptans and amines
  作者：Nasser Zarinderakht、Mohammad Abbasi、Najmeh Nowrouzi

  DOI：10.1002/aoc.6709

  日期：2022.7

  The potential of industrial cobalt phthalocyanines in the synthesis of thioamides is reported. A mixture of an industrial sulfonated cobalt phthalocyanines known as Co[(SO3Na)2,3Pc] (Europhtal catalyst additive 8020) is introduced as an efficient catalyst capable of converting benzyl thiols to synthetically valuable thioamides by reaction with amines and DMSO. In this procedure, different primary and

  报告了工业钴酞菁在硫代酰胺合成中的潜力。引入称为 Co[(SO 3 Na) 2,3 Pc]（Europhtal 催化剂添加剂 8020）的工业磺化钴酞菁混合物作为能够通过与胺和 DMSO 反应将苄硫醇转化为具有合成价值的硫代酰胺的高效催化剂。在该过程中，不同的伯​​胺和仲胺以及杂环胺成功地以高产率转化为苯并硫代酰胺。这种简单的一锅三组分转化方法具有可扩展性，并为合成多种苯硫代酰胺提供了有效且实用的途径。
• Solid-State Photochemistry: Diastereoselective Synthesis of Thietane-Fused .beta.-Lactams from an Acyclic Monothioimide with a Chiral Group
  作者：Masami Sakamoto、Masaki Takahashi、Noriko Hokari、Tsutomu Fujita、Shoji Watanabe

  DOI：10.1021/jo00090a034

  日期：1994.6

  Irradiation of N-[(R)-1-phenylethyl]-N-tigloythiobenzamide in benzene solution resulted in both [2 + 2] thietane and thioketone formation reactions (via beta-hydrogen abstraction by the thiocarbonyl sulfur). Diastereoselectivity in the thietane formation was not observed, in that four beta-lactams were obtained in similar yields. In contrast to the solution photochemistry, irradiation of the crystals provided remarkably high diastereoselectivities. At 15 degrees C, de of the syn-beta-lactams was 61% and the ratio of syn/anti was to 8.7 (chemical yield: 78%). The solid-state photoreaction proceeded even at -78 degrees C, with higher diastereoselectivity. At low conversion (9%), only syn isomers (de = 93%) were obtained, and 71% de was observed even at 90% conversion. An X-ray crystal structure analysis of the monothioimide indicates that the crystal is orthorhombic, of space group P2(1)2(1)2(1), and the distances between the sulfur atom and the alkenyl carbon, and from the thiocarbonyl carbon to the alkenyl carbon, are 4.29 and 3.00 Angstrom, respectively. The twist angle tau of the C(=O)-N bond is 40.8 degrees and that of the C(=S)-N bond is 19.9 degrees. On the other hand, the sulfur atom and abstractable hydrogen atom are in close proximity, and the value for d is 2.40 Angstrom, for theta is 127.3 degrees, for Delta is 67.9 degrees, and for omega is 6.2 degrees. From these values, it is apparent that this reactant is well-positioned for hydrogen transfer in the crystalline state.
• Optically active transition metal complexes 111. Synthesis and structure of a new thioamidato rhodium(I) complex
  作者：Henri Brunner、Jürgen Bügler、Bernhard Nuber

  DOI：10.1016/0957-4166(96)00406-5

  日期：1996.11

  The reaction of [Rh(cod)Cl](2) with deprotonated N-[(A)-1-phenylethyl]thiobenzamide affords the new complex 1. In the solid state 1 exists as a binuclear complex with the two sulfur atoms of two thioamidato ligands bridging the Rh atoms. The molecular structure of 1 was determined by X-ray analysis: C46H52N2S2Rh2, monoclinic, space group C2, a - 10.564(4), b = 16.864(5), c = 23.548(7), beta = 95.05(3)degrees, Z = 2 x 2, R = 0.046, R(w) = 0,039. Complex 1 equilibrates with an isomer in solution at room temperature. Copyright (C) 1996 Published by Elsevier Science Ltd