1-phenyl-3-propylpent-4-en-2-ol

• 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: 1-phenyl-3-propylpent-4-en-2-ol
• 英文别名: 3-Ethenyl-1-phenylhexan-2-ol；3-ethenyl-1-phenylhexan-2-ol
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: RXRPDDMMUYMTJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 (E)-1-bromo-2-hexene 在 tris(dibenzylideneacetone)dipalladium (0) 、 tin(II) trifluoromethanesulfonate lithium hydroxide 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以56%的产率得到1-phenyl-3-propylpent-4-en-2-ol
  参考文献：
  名称：

  Tuning the reactivity of organotin(IV) by LiOH: allylation and propargylation of epoxides via redox transmetalation

  摘要：

  In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.12.008

文献信息

• Barbier reaction in the regime of metal oxide: the first example of carbonyl allylation mediated by tetragonal tin(ii) oxide
  作者：Pradipta Sinha、Sujit Roy

  DOI：10.1039/b104500h

  日期：——

  Facile synthesis of homoallylic alcohols is achieved from allyl halides and aldehydes or ketones over an all-oxide heterogenous media involving beta-SnO and catalytic Cu2O.

  在涉及β-SnO和催化性Cu2O的全氧化物异质介质上，由烯丙基卤和醛或酮可以轻松合成均烯丙基醇。
• Tuning the reactivity of organotin(IV) by LiOH: allylation and propargylation of epoxides via redox transmetalation
  作者：Moloy Banerjee、Ujjal Kanti Roy、Pradipta Sinha、Sujit Roy

  DOI：10.1016/j.jorganchem.2004.12.008

  日期：2005.3

  In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant. (c) 2004 Elsevier B.V. All rights reserved.
• Highly efficient water promoted allylation and propargylation of arylepoxides via rearrangement-carbonyl addition
  作者：Ujjal Kanti Roy、Sujit Roy

  DOI：10.1016/j.tet.2005.10.005

  日期：2006.1

  A simple and highly efficient one-pot procedure for allylation and propargylation of arylepoxides has been developed. A combination of SnCl2 and catalytic Pd(0) or Pd(II) promotes the reaction of organic halides and epoxides in DMSO with controlled water addition, leading to the regioselective formation of the corresponding homoallyl and homopropargyl alcohols in good yields. (c) 2005 Elsevier Ltd. All rights reserved.