1-(4-methoxyphenyl)-3-phenylpropan-2-ol | 64764-53-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-methoxyphenyl)-3-phenylpropan-2-ol
• 英文别名: 1-(4-methoxy-phenyl)-3-phenyl-propan-2-ol；1-Phenyl-3-p-anisyl-2-propanol
• CAS: 64764-53-0
• 化学式: C₁₆H₁₈O₂
• mdl: MFCD13477003
• 分子量: 242.318
• InChiKey: HYFFPNJQTNBWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-3-phenylpropan-2-ol 在 辛酸铑 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 25.17h， 生成
  参考文献：
  名称：

  A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

  摘要：

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.

  DOI：

  10.1021/ol501092m
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-3-phenylpropan-2-one 在 lithium aluminium tetrahydride 作用下， 生成 1-(4-methoxyphenyl)-3-phenylpropan-2-ol
  参考文献：
  名称：

  Electronic Effects in Elimination Reactions. I. Pyrolysis of Acetates¹

  摘要：

  DOI：

  10.1021/ja01571a028

文献信息

• α-Alkylidene-γ-butyrolactone synthesis via one-pot C–H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
  作者：Matthew G. Lloyd、Mariantonietta D'Acunto、Richard J.K. Taylor、William P. Unsworth

  DOI：10.1016/j.tet.2014.09.054

  日期：2015.9

  A system for the synthesis of alpha-alkylidene-gamma-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of alpha-diazoa-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (+/-)-cedarmycins A and B is also described. (C) 2014 Elsevier Ltd. All rights reserved.
• Effect of solvent on .beta.-arylalkyl solvolysis
  作者：Frank L. Schadt、C. J. Lancelot、Paul v. R. Schleyer

  DOI：10.1021/ja00469a040

  日期：1978.1
• Catalyst-Controlled Nitrene Transfer by Tuning Metal:Ligand Ratios: Insight into the Mechanisms of Chemoselectivity
  作者：Cale Weatherly、Juliet M. Alderson、John F. Berry、Jason E. Hein、Jennifer M. Schomaker

  DOI：10.1021/acs.organomet.7b00190

  日期：2017.4.24

  Catalyst.controlled, selective nitrene transfer is often challenging when both C-H and C=C bonds are present in a substrate. Interestingly, a simple change in the Ag(I):L ratio (L = bidentate N,N-donor ligand) enables tunable, chemoselective nitrene transfer that favors either C= C bond aziridination using an similar to 1:1 Ag:L ratio (AgLOTf) or insertion into a C-H bond when the Ag:L ratio in the catalyst is 1:2 (AgL2OTO. In this paper, mechanistic studies, coupled with kinetic profiling of the entire reaction course, are employed to examine the reasons for this unusual behavior. Steady-state kinetics were found to be similar for both AgLOTf and AgL2OTf; both complexes yield electronically similar reactive intermediates that engage in nitrene transfer involving formation of a short-lived radical intermediate and barrierless radical recombination. Taken together,, experimental and computational studies point to two effects that control tunable: cherrioSelectiVity: suppression of aziridination as the steric congestion around the silver center is increased in AgL2OTf and a decrease in the rate of C-H insertion with AgLOTf in comparison to AgL2OTE The observation that the sterics of Ag catalysts can be varied, with minor effects on the electronic features of the putative nitrene, has important implications for the development of other silver catalysts that enable tunable, site-selective C-H bond aminations..