4-isobutyl-1,3-thiazolidine-2-thione | 84347-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-isobutyl-1,3-thiazolidine-2-thione
• 英文别名: 4-(2-methylpropyl)thiazolidine-2-thione；4-(2-Methylpropyl)-1,3-thiazolidine-2-thione
• CAS: 84347-30-8
• 化学式: C₇H₁₃NS₂
• 分子量: 175.319
• InChiKey: YTCCBPWGHFWCNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲基乙酰氯 、 4-isobutyl-1,3-thiazolidine-2-thione 生成 4-isobutyl-3-pivaloyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Yamada, Shinji, Angewandte Chemie, 1995, vol. 107, # 10, p. 1224 - 1226

  摘要：

  DOI：
• 作为产物：
  描述：

  二硫化碳 、 DL-亮氨醇 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以58%的产率得到4-isobutyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Effects of C(O)−N Bond Rotation on the ¹³C, ¹⁵N, and ¹⁷O NMR Chemical Shifts, and Infrared Carbonyl Absorption in a Series of Twisted Amides

  摘要：

  A series of the C(O)-N twisted amides, 3-acyl-4-alkyl-1,3-thiazolidine-2-thiones la-e, was synthesized, and the structures were elucidated by X-ray crystallographic analysis. The relationship between the C(O)-N twist angles tau, the C-13, N-15, and O-17 NMR chemical shifts, and the infrared absorption of carbonyl groups were investigated in order to provide insight into the changes in charge distribution dependence on the C(O)-N twist angle. Furthermore, the relationship of the v(C=O) and the N-15 chemical shift was also investigated. Because the spectral data reflect considerable substituent effects, the C-13 and O-17 chemical shifts and v(C=O) were compared with those of corresponding N,N-dimethylamides 2a-c, and the N-15 chemical shifts were compared with those of corresponding N-methyl-1,3-thiazolidine-2-thiones 3a-c. As the twist angle increased, the Delta delta(13)C and Delta delta(17)O increased, whereas, the Delta delta(15)N decreased. Furthermore, the Delta v(C=O) increased with increasing tau and decreased with increasing Delta delta(15)N. Th, relationship of the results to the classical amide resonance model and recently proposed model is also discussed.

  DOI：

  10.1021/jo9516953

文献信息

• Yamada, Shinji, Angewandte Chemie, 1995, vol. 107, # 10, p. 1224 - 1226
  作者：Yamada, Shinji

  DOI：——

  日期：——
• CAMBIE, R. C.;RUTLEDGE, P. S.;STRANGE, G. A.;WOODGATE, P. D., HETEROCYCLES, 1982, 19, N 10, 1903-1908
  作者：CAMBIE, R. C.、RUTLEDGE, P. S.、STRANGE, G. A.、WOODGATE, P. D.

  DOI：——

  日期：——
• US4631270A
  申请人：——

  公开号：US4631270A

  公开（公告）日：1986-12-23
• Effects of C(O)−N Bond Rotation on the ¹³C, ¹⁵N, and ¹⁷O NMR Chemical Shifts, and Infrared Carbonyl Absorption in a Series of Twisted Amides
  作者：Shinji Yamada

  DOI：10.1021/jo9516953

  日期：1996.1.1

  A series of the C(O)-N twisted amides, 3-acyl-4-alkyl-1,3-thiazolidine-2-thiones la-e, was synthesized, and the structures were elucidated by X-ray crystallographic analysis. The relationship between the C(O)-N twist angles tau, the C-13, N-15, and O-17 NMR chemical shifts, and the infrared absorption of carbonyl groups were investigated in order to provide insight into the changes in charge distribution dependence on the C(O)-N twist angle. Furthermore, the relationship of the v(C=O) and the N-15 chemical shift was also investigated. Because the spectral data reflect considerable substituent effects, the C-13 and O-17 chemical shifts and v(C=O) were compared with those of corresponding N,N-dimethylamides 2a-c, and the N-15 chemical shifts were compared with those of corresponding N-methyl-1,3-thiazolidine-2-thiones 3a-c. As the twist angle increased, the Delta delta(13)C and Delta delta(17)O increased, whereas, the Delta delta(15)N decreased. Furthermore, the Delta v(C=O) increased with increasing tau and decreased with increasing Delta delta(15)N. Th, relationship of the results to the classical amide resonance model and recently proposed model is also discussed.

表征谱图