methyl 1-(hydroxy(phenyl)methyl)cyclopropane-1-carboxylate | 1227176-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 1-(hydroxy(phenyl)methyl)cyclopropane-1-carboxylate
• CAS: 1227176-45-5
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: WGPYGELQINNCRK-UHFFFAOYSA-N

物化性质

• 沸点：
  307.8±15.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-氯丁酸甲酯 、 苯甲醛 在 potassium tert-butylate 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到methyl trans-2-phenyltetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes

  摘要：

  Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intra-molecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has eleetron-donatine groups.

  DOI：

  10.1021/jo1002196