3-phenyl-3-p-tolylpropan-1-ol | 51714-27-3

• 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: 3-phenyl-3-p-tolylpropan-1-ol
• 英文别名: 3-(4'-Methylphenyl)-3-phenylpropan-1-ol；3-oxy-1-phenyl-1-p-tolyl-propane；3-Oxy-1-phenyl-1-p-tolyl-propan；γ-Phenyl-γ-p-tolyl-propylalkohol；3-(4-Methylphenyl)-3-phenylpropan-1-ol；3-(4-methylphenyl)-3-phenylpropan-1-ol
• CAS: 51714-27-3
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: IKJHRABPTIMQGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-p-tolylpropan-1-ol 在 氢溴酸 作用下， 生成 4-phenyl-4-p-tolyl-butyronitrile
  参考文献：
  名称：

  v. Braun; Manz; Reinsch, Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 288

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基二苯氯甲烷 在 氢氧化钾 、 lithium aluminium tetrahydride 、 sodium hydride 、 sodium iodide 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.17h， 生成 3-phenyl-3-p-tolylpropan-1-ol
  参考文献：
  名称：

  Ring-substituted histaprodifen analogues as partial agonists for histamine H1 receptors: synthesis and structure–activity relationships

  摘要：

  Thirteen racemic benzene ring-substituted analogues of histaprodifen (8a; 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethanamine), a novel lead for potent and selective histamine H-1-receptor agonists, have been prepared from substituted 4,4-diphenylbutyronitriles 5 via cyclization of the corresponding methyl butyrimidates 6 with 2-oxo-4-phthalimido-1-butyl acetate in liquid ammonia, followed by deprotection. Nitriles 5 were accessible by alkylation of either substituted diphenylmethanes with 3-bromopropionitrile or diethyl malonate with substituted 1-chloro-diphenylmethanes and subsequent standard reactions. The title compounds 8 displayed partial agonism on contractile H-1 receptors of the guinea-pig ileum (E-max = 2-98% relative to histamine) and, compared with the endogenous agonist, were endowed with agonist potencies of 4-92%. The meta fluorinated (gc) and meta chlorinated (8f) analogues showed the highest relative potency in this series (95% confidence Limits 85-99% and 78-102%), but did not exceed the value of the lead 8a (99-124%). Compound 8c (2-[2-[3-(3-fluorophenyl)-3-phenylpropyl]-1H-imidazol-4-yl]ethanamine) was a partial agonist at contractile H-1 receptors of the guinea-pig aorta (relative potency 154% vs. 100% for histamine) and at relaxation-mediating endothelial H-1 receptors of the rat aorta (relative potency 556% vs. 100% for histamine) and matched with the functional behaviour of 8a. Agonism observed for each compound was sensitive to blockade by the selective H-1-receptor antagonist mepyramine (pA(2) approximate to 9 (guinea-pig) and pA(2) approximate to 8 (rat aorta)). All histaprodifen analogues 8 stimulated neither histaminergic H-2/H-3, nor cholinergic M-3 receptors. They displayed only low to moderate affinity for these sites (H-2: pD'(2), < 5; H-3/M-3: pA(2) < 6). With regard to the substitution pattern on the benzene ring, there was no correlation between the histaprodifen series and the corresponding derivatives of another selective H-1-receptor agonist, viz. 2-phenylhistamine. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00105-7

文献信息

• Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes
  作者：Christian Ebner、Andreas Pfaltz

  DOI：10.1016/j.tet.2011.10.051

  日期：2011.12

  A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center

  制备了一种基于2,3-二氢苯并[1,4]恶嗪结构的新型有机催化剂，并将其用于以Hantzsch酯为氢化物供体的α，β-不饱和醛的对映选择性转移加氢。这些催化剂被证明对于共轭还原β，β-二芳基取代的丙烯醛特别有效，从而导致带有两个立体不同的芳基的立体异构中心的立体醛，对映选择性高达91％ee。
• Ring-opening 1,3-arylboration of arylcyclopropanes mediated by BCl₃
  作者：Yuichi Kuboki、Mitsuhiro Arisawa、Kenichi Murai

  DOI：10.1039/d0ra08151e

  日期：——

  Herein, we report a ring-opening 1,3-arylboration of aryl cyclopropanes using BCl3 in the presence of arene nucleophiles. Formal 1,3-oxy arylation and 1,3-amino arylation of the arylcyclopropane via one-pot derivatization of the installed boron group were also achieved.

  在此，我们报道了在芳烃亲核试剂存在下使用 BCl 3对芳基环丙烷进行 1,3-芳基硼化反应。通过安装的硼基团的一锅衍生化，还实现了芳基环丙烷的正式 1,3-氧基芳基化和 1,3-氨基芳基化。
• Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds
  作者：Sureshbabu Guduguntla、Valentín Hornillos、Romain Tessier、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1021/acs.orglett.5b03396

  日期：2016.1.15

  A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities

  提出了高度对映选择性的铜/ N-杂环卡宾与有机锂化合物的烯丙基芳基化反应。在与烯丙基溴的反应中使用市售或易于制备的芳基锂试剂可提供高收率的多种手性二芳基乙烯基甲烷，其在药物中具有优先的结构基序，具有良好或优异的区域和对映选择性。市售药物托特罗定（Detrol）的正式合成中说明了这种新转变的多功能性。
• Virtanen,P.O.I. et al., Acta Chemica Scandinavica (1947), 1973, vol. 27, p. 3944 - 3952
  作者：Virtanen,P.O.I. et al.

  DOI：——

  日期：——