1-[(4R)-4-苯基-2-硫代-3-噻唑烷基]-1-丙酮 | 1039757-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 1-[(4R)-4-苯基-2-硫代-3-噻唑烷基]-1-丙酮
• 英文名称: (S)-4-phenyl-N-propanoyl-1,3-thiazolidine-2-thione
• 英文别名: (S)-N-propionyl-4-phenylthiazolidine-2-thione；(S)-4-Phenyl-3-propionyl-1,3-thiazolidine-2-thione；1-[(4S)-4-phenyl-2-sulfanylidene-1,3-thiazolidin-3-yl]propan-1-one
• CAS: 1039757-81-7
• 化学式: C₁₂H₁₃NOS₂
• 分子量: 251.373
• InChiKey: LGVYUGKSBWUYOP-SNVBAGLBSA-N

物化性质

• 沸点：
  380.9±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1-[(4R)-4-苯基-2-硫代-3-噻唑烷基]-1-丙酮 、 对氯苯异氰酸酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(S)-N-(4-chlorophenyl)-4-phenyl-2-thioxothiazolidine-3-carboxamide
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives

  摘要：

  A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 mu g/mL and 6.5 mu g/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 mu g/mL, 12.1 mu g/mL, and 11.0 mu g/mL, respectively.

  DOI：

  10.1080/10426507.2014.931399
• 作为产物：
  描述：

  L-苯甘氨醇 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 1-[(4R)-4-苯基-2-硫代-3-噻唑烷基]-1-丙酮
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives

  摘要：

  A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 mu g/mL and 6.5 mu g/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 mu g/mL, 12.1 mu g/mL, and 11.0 mu g/mL, respectively.

  DOI：

  10.1080/10426507.2014.931399

文献信息

• 一种酰基化硫代恶唑烷酮的合成方法
  申请人：上海百灵医药科技有限公司

  公开号：CN109020913A

  公开（公告）日：2018-12-18

  本发明公开了一种酰基化硫代恶唑烷酮的合成方法。本发明的合成方法，其包括如下步骤：非质子有机溶剂中，在化合物III和缚酸剂的作用下，将化合物I与化合物II进行酰胺化反应，得到化合物IV。本发明的方法能够在温和条件下进行，收率高、纯度高，适用于工业化生产的需求。
• On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals
  作者：Jessica Baiget、Annabel Cosp、Erik Gálvez、Loreto Gómez-Pinal、Pedro Romea、Fèlix Urpí

  DOI：10.1016/j.tet.2008.04.044

  日期：2008.6

  Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded good results, but the corresponding oxazolidinones resulted completely unselective for such reactions, which proves that an exocyclic C=S bond is essential to attain a synthetically useful stereocontrol. (C) 2008 Elsevier Ltd. All rights reserved.
• Absolute Configuration of Lactams and Oxazolidinones Using Kinetic Resolution Catalysts
  作者：Matthew A. Perry、Jonathan V. Trinidad、Scott D. Rychnovsky

  DOI：10.1021/ol303239t

  日期：2013.2.1

  A simple method for determining the absolute configuration of oxazolidinones, lactams, and their derivatives using kinetic resolution catalysts is described. The optically pure substrates were acylated using the (S)-HBTM and the (R)-HBTM catalyst, and the faster reaction was determined. An empirical mnemonic was developed for the assignment of the absolute configuration based on the fast-reacting catalyst.