(3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic acid | 252192-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic acid
• 英文别名: (3R,4S)-4-butylthiolane-3-carboxylic acid
• CAS: 252192-77-1
• 化学式: C₉H₁₆O₂S
• 分子量: 188.291
• InChiKey: IKRJROHUSLKPBD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic acid 在 镍 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 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 lithium hydroxide 、 甲基溴化镁 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 103.5h， 生成 (3R,4S)-4-butyl-tetrahydrothiophene-3-carboxylic 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

文献信息

• Enantiomerically Pure <i>trans</i>-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1021/ol9910565

  日期：1999.11.1

  [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.