(E)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylsulfanyl)-3-hydroxy-but-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester | 200569-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (E)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylsulfanyl)-3-hydroxy-but-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS: 200569-84-2
• 化学式: C₂₂H₂₇NO₅S
• 分子量: 417.526
• InChiKey: UXBNUDQHTNTDHP-VZXRESSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylsulfanyl)-3-hydroxy-but-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 在 吡啶 作用下， 以 氘代氯仿 为溶剂， 生成 3-Oxo-2-thioxo-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  α,α′-Dioxothiones part 2. Asymmetric Diels-Alder reactions of chiral non-racemic α,α′-dioxothiones

  摘要：

  Chiral non-racemic alpha,alpha'-dioxothiones 2a-g and 17 are obtained from chiral beta-ketoesters using the phthalimidesulfenyl chloride 1 as key reagent. The ability of these thiones to discriminate between the enantiotopic faces of several dienophiles has been evaluated, The best diastereoisomeric excesses (67-80%) were obtained when the alpha-acyl thiones were involved as electron-poor dienes in inverse electron demand Diels-Alder reactions with electron-rich styrenes as dienophiles. The possibility to obtain thiones bearing two,chiral groups as-well as the reactions where the alpha-acyl thiones 2 participate as dienophiles are also shown. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10162-4
• 作为产物：
  描述：

  L-薄荷醇 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (E)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylsulfanyl)-3-hydroxy-but-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  α,α′-Dioxothiones part 2. Asymmetric Diels-Alder reactions of chiral non-racemic α,α′-dioxothiones

  摘要：

  Chiral non-racemic alpha,alpha'-dioxothiones 2a-g and 17 are obtained from chiral beta-ketoesters using the phthalimidesulfenyl chloride 1 as key reagent. The ability of these thiones to discriminate between the enantiotopic faces of several dienophiles has been evaluated, The best diastereoisomeric excesses (67-80%) were obtained when the alpha-acyl thiones were involved as electron-poor dienes in inverse electron demand Diels-Alder reactions with electron-rich styrenes as dienophiles. The possibility to obtain thiones bearing two,chiral groups as-well as the reactions where the alpha-acyl thiones 2 participate as dienophiles are also shown. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10162-4