(-)-(3'R,4'R,5'S)-3-[(2',3'-diphenyl-5'-methylisoxazolidin-4'-yl)carbonyl]-1,3-thiazolidin-2-thione | 851078-02-9

• 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'R,4'R,5'S)-3-[(2',3'-diphenyl-5'-methylisoxazolidin-4'-yl)carbonyl]-1,3-thiazolidin-2-thione
• 英文别名: [(3R,4R,5S)-5-methyl-2,3-diphenyl-1,2-oxazolidin-4-yl]-(2-sulfanylidene-1,3-thiazolidin-3-yl)methanone
• CAS: 851078-02-9
• 化学式: C₂₀H₂₀N₂O₂S₂
• 分子量: 384.523
• InChiKey: ZCEGHPGWGZJJTF-WBAXXEDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(3'R,4'R,5'S)-3-[(2',3'-diphenyl-5'-methylisoxazolidin-4'-yl)carbonyl]-1,3-thiazolidin-2-thione 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以53%的产率得到(3,4-cis;4,5-trans) 4-hydroxymethyl-5-methyl-2,3-diphenyl-isoxazolidine
  参考文献：
  名称：

  Highly Exo-Selective and Enantioselective Cycloaddition Reactions of Nitrones Catalyzed by a Chiral Binaphthyldiimine−Ni(II) Complex

  摘要：

  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.

  DOI：

  10.1021/ol050397h
• 作为产物：
  描述：

  C,N-diphenylnitrone 、 (E)-1-(2-thioxothiazolidin-3-yl)but-2-en-1-one 在 (R)-BINIM-DCOH 、 nickel(II) perchlorate 作用下， 以 氯仿 为溶剂， 反应 15.0h， 生成 (-)-(3'R,4'R,5'S)-3-[(2',3'-diphenyl-5'-methylisoxazolidin-4'-yl)carbonyl]-1,3-thiazolidin-2-thione 、 (+)-(3'S,4'S,5'R)-3-[(2',3'-diphenyl-5'-methylisoxazolidin-4'-yl)carbonyl]-1,3-thiazolidin-2-thione
  参考文献：
  名称：

  Highly Exo-Selective and Enantioselective Cycloaddition Reactions of Nitrones Catalyzed by a Chiral Binaphthyldiimine−Ni(II) Complex

  摘要：

  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.

  DOI：

  10.1021/ol050397h

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.