(1R,2E,4S)-6,6-dimethyl-1-phenylhept-2-ene-1,4-diol | 914248-50-3

• 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: (1R,2E,4S)-6,6-dimethyl-1-phenylhept-2-ene-1,4-diol
• CAS: 914248-50-3
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BYZPURSGDFRBNW-NPUYYSGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (1R,2E,4S)-6,6-dimethyl-1-phenylhept-2-ene-1,4-diol 在 二(氰基苯)二氯化钯 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 (1E,3S,4S)-4-acetoxy-6,6-dimethyl-1-phenylhept-1-en-3-yl acetate
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539
• 作为产物：
  描述：

  (R)-(+)-1-phenylprop-2-yn-1-yl acetate 在 lithium aluminium tetrahydride 、 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.5h， 生成 (1R,2E,4S)-6,6-dimethyl-1-phenylhept-2-ene-1,4-diol
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539