(4R)-6-phenylhexane-1,4-diol | 2430-76-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R)-6-phenylhexane-1,4-diol
• CAS: 2430-76-4；138298-27-8
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: AENKSWXGVMDUPU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4R)-6-phenylhexane-1,4-diol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以70%的产率得到2-(2-phenylethyl)tetrahydrofuran
  参考文献：
  名称：

  Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

  摘要：

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.

  DOI：

  10.1016/s0040-4020(01)81944-x
• 作为产物：
  描述：

  6-phenyl-4-oxohexanoic acid 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 葡萄糖 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 (4R)-6-phenylhexane-1,4-diol
  参考文献：
  名称：

  Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

  摘要：

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.

  DOI：

  10.1016/s0040-4020(01)81944-x

文献信息

• One-Pot Asymmetric Synthesis of 2- and 2,3-Disubstituted Tetrahydrofuran Derivatives
  作者：P. Veeraraghavan Ramachandran、Hari N. G. Nair、Pravin D. Gagare

  DOI：10.1021/jo300414u

  日期：2012.6.15

  A novel and convenient one-pot asymmetric synthesis of 2- and 2,3-disubstituted tetrahydrofurans has been achieved in 56-81% yields and 86-99% ee from aliphatic and aromatic aldehydes via an allyl/crotyl/alkoxyallylboration-hydroboration-iodination-cyclization reaction sequence.