(3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam | 252192-74-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam
• 英文别名: [(3R,4S)-4-butylthiolan-3-yl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone；[(3R,4S)-4-butylthiolan-3-yl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone
• CAS: 252192-74-8
• 化学式: C₁₉H₃₁NO₃S₂
• 分子量: 385.592
• InChiKey: HXWLKXLCTJHHBV-DINLJIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam 在 镍 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 7.0h， 生成 (2R,3S)-2,3-dimethylheptanoic acid
  参考文献：
  名称：

  Enantiomerically Pure trans-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides

  摘要：

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.

  DOI：

  10.1021/ol9910565
• 作为产物：
  描述：

  (E)-Hept-2-enoyl chloride 在 甲基溴化镁 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 97.5h， 生成 (3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam
  参考文献：
  名称：

  Enantiomerically Pure trans-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides

  摘要：

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.

  DOI：

  10.1021/ol9910565