[(E)-3-(1-cyclohexylprop-2-enoxy)prop-1-enyl]benzene | 193558-98-4

• 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: [(E)-3-(1-cyclohexylprop-2-enoxy)prop-1-enyl]benzene
• CAS: 193558-98-4
• 化学式: C₁₈H₂₄O
• 分子量: 256.388
• InChiKey: RJDRVBIXOAIXPQ-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(E)-3-(1-cyclohexylprop-2-enoxy)prop-1-enyl]benzene 在 吡啶 、 sodium chlorite 、 potassium phosphate 、 2-甲基-2-丁烯 、 18-冠醚-6 、 potassium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (4S,6R)-5-Cyclohexyl-4-phenyl-6-phenylselanylmethyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Synthetic Applications (II) of the Tandem [2,3]-Wittig-Anionic Oxy-Cope Rearrangement: Stereoselective Trisubstituted δ-Lactone and Tetrahydropyran Synthesis

  摘要：

  Di-and trisubstituted delta-lactones have been prepared by stereoselective iodolactonisation and phenylselenolactonisation of delta,epsilon-unsaturated carboxylic acids. The acyclic stereochemistry of the acids arises from highly stereoselective tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of cinnamyl ethers with potassium hydride and 18-crown-6 in THF to give delta,epsilon-unsaturated aldehydes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01475-5
• 作为产物：
  描述：

  1-环己基-2-丙醇 、 Cinnamyl bromide 在 15-冠醚-5 、 四丁基碘化铵 、 sodium hydride 作用下， 反应 12.0h， 以98%的产率得到[(E)-3-(1-cyclohexylprop-2-enoxy)prop-1-enyl]benzene
  参考文献：
  名称：

  An improved Williamson etherification of hindered alcohols promoted by 15-crown-5 and sodium hydride

  摘要：

  15-crown-5 greatly facilitates Williamson ether synthesis when sodium hydride base is used in THF solvent. This mild yet versatile procedure has been employed in the synthesis of new homochiral polyether ligands and bis-allylic ethers which are inaccessible by conventional methods. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00965-9

文献信息

• An improved Williamson etherification of hindered alcohols promoted by 15-crown-5 and sodium hydride
  作者：Helen C. Aspinall、Nicholas Greeves、Wai-Man Lee、Edward G. McIver、Peter M. Smith

  DOI：10.1016/s0040-4039(97)00965-9

  日期：1997.6

  15-crown-5 greatly facilitates Williamson ether synthesis when sodium hydride base is used in THF solvent. This mild yet versatile procedure has been employed in the synthesis of new homochiral polyether ligands and bis-allylic ethers which are inaccessible by conventional methods. (C) 1997 Elsevier Science Ltd.
• Synthetic Applications (II) of the Tandem [2,3]-Wittig-Anionic Oxy-Cope Rearrangement: Stereoselective Trisubstituted δ-Lactone and Tetrahydropyran Synthesis
  作者：Nicholas Greeves、Wai-Man Lee、Jim V. Barkley

  DOI：10.1016/s0040-4039(97)01475-5

  日期：1997.9

  Di-and trisubstituted delta-lactones have been prepared by stereoselective iodolactonisation and phenylselenolactonisation of delta,epsilon-unsaturated carboxylic acids. The acyclic stereochemistry of the acids arises from highly stereoselective tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of cinnamyl ethers with potassium hydride and 18-crown-6 in THF to give delta,epsilon-unsaturated aldehydes. (C) 1997 Elsevier Science Ltd.