cis-3-(4-octyl-4-phenylcyclohexa-2,5-dienyl)pentan-3-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: cis-3-(4-octyl-4-phenylcyclohexa-2,5-dienyl)pentan-3-ol
• 英文别名: trans-3-(4-octyl-4-phenylcyclohexa-2,5-dienyl)pentan-3-ol
• 化学式: C₂₅H₃₈O
• 分子量: 354.576
• InChiKey: VUWLNTIXIFUNIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  联苯 、 1-氟辛烷 、 3-戊酮 以61%的产率得到cis-3-(4-octyl-4-phenylcyclohexa-2,5-dienyl)pentan-3-ol
  参考文献：
  名称：

  Reductive dearomatization of biphenyl: sequential one-pot regioselective introduction of two different electrophiles

  摘要：

  The reaction of biphenyl (1) with an excess of lithium in THF at room temperature leads to a solution of the corresponding dianion (I), which by successive reactions with an alkyl fluoride [E-1 = n-C8H17F, c-C5H9CH2F, CH2=CH(CH2)(4)F] at 0 degrees C and another electrophile [E-2 = n-C4H9Br, Et2CO, Me2C(O)CH2, i-Pr3SiCl] at -78 degrees C yields the corresponding 1,4-disubstituted 1,4-dihydrobiphenyls 3 in a regioselective manner, as mixtures of cis- and trans-isomers. The diastercomers of 3 are separated by column chromatography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.013

文献信息

• The reaction of biphenyl radical anion and dianion with alkyl fluorides. From ET to SN2 reaction pathways and synthetic applications
  作者：Henoc Pérez、Cristóbal Melero、Albert Guijarro、Miguel Yus

  DOI：10.1016/j.tet.2009.09.027

  日期：2009.12

  dilithium biphenyl (Li2C12H10) with alkyl fluorides has been studied from the point of view of the distribution of products. Two main reaction pathways, the nucleophilic substitution (SN2) and the electron transfer (ET), can compete to yield the same alkylation products in what is known as the SN2–ET dichotomy. SN2 seems to be the main mechanism operating with primary alkyl fluorides (n-RF). Alkylation proceeds

  从产物分布的观点出发，已经研究了二锂联苯基（Li 2 C 12 H 10）与烷基氟化物的反应。两种主要的反应途径，亲核取代（S N 2）和电子转移（ET），可以竞争产生相同的烷基化产物，即所谓的S N 2–ET二分法。S N 2似乎是与伯烷基氟化物（n -RF）相互作用的主要机理。烷基化反应的收率很高，所得的烷基化二氢联苯阴离子（n -RC 12 H 10 Li）可以用第二种常规亲电试剂（E +），得到了合成上令人感兴趣的脱芳香化联苯衍生物（n -RC 12 H 10 E）。随着我们向仲（s -RF）和叔烷基氟化物（t -RF）的转移，反应产生了更多的ET产物，在这种情况下，该机理似乎主要由ET主导。在这种情况下，烷基化通过自由基偶合仍然可行，从而获得合成吨-RC 12 ħ 10 E，虽然在较低的产率。对这个S N的合理解释基于将5-己烯基氟化物和1,1-二甲基-5-己烯基氟化物用作与Li
• Reductive dearomatization of biphenyl: sequential one-pot regioselective introduction of two different electrophiles
  作者：Cristóbal Melero、Henoc Pérez、Albert Guijarro、Miguel Yus

  DOI：10.1016/j.tetlet.2007.04.013

  日期：2007.6

  The reaction of biphenyl (1) with an excess of lithium in THF at room temperature leads to a solution of the corresponding dianion (I), which by successive reactions with an alkyl fluoride [E-1 = n-C8H17F, c-C5H9CH2F, CH2=CH(CH2)(4)F] at 0 degrees C and another electrophile [E-2 = n-C4H9Br, Et2CO, Me2C(O)CH2, i-Pr3SiCl] at -78 degrees C yields the corresponding 1,4-disubstituted 1,4-dihydrobiphenyls 3 in a regioselective manner, as mixtures of cis- and trans-isomers. The diastercomers of 3 are separated by column chromatography. (c) 2007 Elsevier Ltd. All rights reserved.