3-((5R,8S,9R)-1-methyl-4-oxo-3,9-diphenyl-6-thioxo-2,3,7-triazaspiro[4.4]non-1-enecarbonyl)oxazolidin-2-one | 1404553-96-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-((5R,8S,9R)-1-methyl-4-oxo-3,9-diphenyl-6-thioxo-2,3,7-triazaspiro[4.4]non-1-enecarbonyl)oxazolidin-2-one
• 英文别名: 3-[(5R,8S,9R)-1-methyl-4-oxo-3,9-diphenyl-6-sulfanylidene-2,3,7-triazaspiro[4.4]non-1-ene-8-carbonyl]-1,3-oxazolidin-2-one
• CAS: 1404553-96-3
• 化学式: C₂₃H₂₀N₄O₄S
• 分子量: 448.502
• InChiKey: TYVPTWHDOLLGNA-IUKKYPGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-isothiocyanato-acetyl)-oxazolidin-2-one 、 4-benzylidene-3-methyl-1-phenylpyrazolone 在 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到
  参考文献：
  名称：

  Core Scaffold-Inspired Stereoselective Synthesis of Spiropyrazolones via an Organocatalytic Michael/Cyclization Sequence

  摘要：

  Herein, the organocatalytic asymmetric Michael/cyclization sequence of alpha-isothiocyanato imides and esters with a variety of unsaturated pyrazolones is presented, in general, affording functionalized spiropyrazolones containing three contiguous stereogenic centers in high levels of diastereo- and enantioselectivity (up to 20:1 dr and 99% ee). Moreover, the current protocol provides a highly efficient and convenient strategy that allows rapid enantioselective construction of diversely spiropyrazolone skeletons with high optical purity.

  DOI：

  10.1021/jo301851a

文献信息

• Core Scaffold-Inspired Stereoselective Synthesis of Spiropyrazolones via an Organocatalytic Michael/Cyclization Sequence
  作者：Luping Liu、Yuan Zhong、Panpan Zhang、Xianxing Jiang、Rui Wang

  DOI：10.1021/jo301851a

  日期：2012.11.16

  Herein, the organocatalytic asymmetric Michael/cyclization sequence of alpha-isothiocyanato imides and esters with a variety of unsaturated pyrazolones is presented, in general, affording functionalized spiropyrazolones containing three contiguous stereogenic centers in high levels of diastereo- and enantioselectivity (up to 20:1 dr and 99% ee). Moreover, the current protocol provides a highly efficient and convenient strategy that allows rapid enantioselective construction of diversely spiropyrazolone skeletons with high optical purity.