(1S,2E,4R)-4-acetoxy-1-cyclohexyl-4-phenylbut-2-enyl acetate | 914248-58-1

• 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: (1S,2E,4R)-4-acetoxy-1-cyclohexyl-4-phenylbut-2-enyl acetate
• 英文别名: [(E,1S,4R)-4-acetyloxy-1-cyclohexyl-4-phenylbut-2-enyl] acetate
• CAS: 914248-58-1
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: KNXNOJLGLSGPQW-CUVMAEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2E,4R)-4-acetoxy-1-cyclohexyl-4-phenylbut-2-enyl acetate 在 二(氰基苯)二氯化钯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到(1S,2S,3E)-2-acetoxy-1-cyclohexyl-4-phenylbut-3-enyl 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：

  (+/-)-1-苯基-2-丙炔-1-醇 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 Novozym 435 、 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.5h， 生成 (1S,2E,4R)-4-acetoxy-1-cyclohexyl-4-phenylbut-2-enyl 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

文献信息

• 1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains
  作者：Xavier Ariza、Jordi Garcia、Yohan Georges、Mar Vicente

  DOI：10.1021/ol0616539

  日期：2006.9.1

  (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.