(3R,4R)-4-phenyl-tetrahydrothiophene-3-carboxylic acid | 252192-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R)-4-phenyl-tetrahydrothiophene-3-carboxylic acid
• 英文别名: (3R,4R)-4-phenylthiolane-3-carboxylic acid
• CAS: 252192-81-7
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: ZABHZUNEOJIABN-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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,4R)-4-phenyl-tetrahydrothiophene-3-carboxylic acid 在 镍 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (+/-)-erythro-2-methyl-3-phenyl-butyric 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：

  (3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 在 lithium hydroxide 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 102.0h， 生成 (3R,4R)-4-phenyl-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