3-(2-hexenoyl)-2-thiazolidinethione | 851078-04-1

• 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: 3-(2-hexenoyl)-2-thiazolidinethione
• 英文别名: 1-(2-thioxothiazolidin-3-yl)hex-2-en-1-one；(E)-1-(2-sulfanylidene-1,3-thiazolidin-3-yl)hex-2-en-1-one
• CAS: 851078-04-1
• 化学式: C₉H₁₃NOS₂
• 分子量: 215.34
• InChiKey: UZQLQJPQLDDTID-SNAWJCMRSA-N

物化性质

• 沸点：
  309.5±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hexenoyl)-2-thiazolidinethione 在 [Ni((S)-Tol-BINAP)](BF₄)2 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 tert-butyl (R)-2-methyl-6-oxo-4-propyl-5,6-dihydro-4H-pyran-3-carboxylate
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated N-Acylthiazolidinethiones

  摘要：

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.

  DOI：

  10.1021/ja053820q
• 作为产物：
  描述：

  2-巯基噻唑啉 、 (E)-2-己烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到3-(2-hexenoyl)-2-thiazolidinethione
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated N-Acylthiazolidinethiones

  摘要：

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.

  DOI：

  10.1021/ja053820q

文献信息

• Highly <i>Exo</i>-Selective and Enantioselective Cycloaddition Reactions of Nitrones Catalyzed by a Chiral Binaphthyldiimine−Ni(II) Complex
  作者：Hiroyuki Suga、Takuya Nakajima、Kengo Itoh、Akikazu Kakehi

  DOI：10.1021/ol050397h

  日期：2005.3.1

  Significant levels of exo-selectivity (exo:endo = > 99:1 to 86:14) and enantioselectivity (95-82% ee) were obtained in the 1,3-dipolar cycloadditions of a number of nitrones with 3-(2-alkenoyl)-2-thiazolidinethiones, using the chiral binaphthyidiimine-Ni(II) complex (5-20 mol %), which was easily prepared form N,N'-bis(3,5-dichrolo-2-hydroxybenzylidene)-1,1'-binaphthyl-2,2'-diamine and Ni(ClO4)2(.)6H(2)O in CHCl3 in the presence of 4 angstrom molecular sieves, as a chiral Lewis acid catalyst.