2-(4-methoxyphenyl)-2-methyloxirane | 42432-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-2-methyloxirane
• 英文别名: 1,2-epoxy-2-(4'-methoxyphenyl)propane
• CAS: 42432-42-8
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: OHILVLMNCBTDJI-UHFFFAOYSA-N

物化性质

• 沸点：
  242.7±28.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-2-methyloxirane 在 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 为溶剂， 以2 g的产率得到2-(4-methoxyphenyl)allylalcohol
  参考文献：
  名称：

  加氢甲酰化合成季碳中心

  摘要：

  报道了加氢甲酰化在合成季碳中心中的应用。高度取代的碳的合成是通过施加催化量的 1 来实现的。配体 1 通过与底物和催化剂共价且可逆地结合作为催化导向基团。导向基团策略的分子内性质加速了加氢甲酰化反应，使得反应在温和的温度（35-55 摄氏度）下进行，并具有出色的区域选择性（b:l > 94:6）。

  DOI：

  10.1021/ja1036226
• 作为产物：
  描述：

  1-异丙烯基-4-甲氧基苯 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-(4-methoxyphenyl)-2-methyloxirane
  参考文献：
  名称：

  Reaktivit�t und Selektivit�t bei der Oxidation von Styrolderivaten, II. Untersuchungen zur Oxidation vonp-substituierten ?-Methylstyrolen

  摘要：

  The liquid phase oxidation of p-substituted (Br-, Cl-, t-Bu-, MeO-, CF3-) alpha-methylstyrenes and of alpha,p-dimethoxystyrene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125 degrees C. The product yields were determined gaschromatographically. The differences of the activation energies of the epoxide formation and the parallel reactions amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and concentration of olefine. The relative chain propagation constants k(p) (C=C) Were determined by competitive oxidation with cumene. The k(p)(C=C) values of p-substituted alpha-methylstyrenes can be correlated by the Hammett equation with both sigma and sigma(+) substituent constants.

  DOI：

  10.1002/prac.19963380147

文献信息

• Mild Iridium‐Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β‐Alkyl Amines
  作者：Albert Cabré、Juanjo Cabezas‐Giménez、Giuseppe Sciortino、Gregori Ujaque、Xavier Verdaguer、Agustí Lledós、Antoni Riera

  DOI：10.1002/adsc.201900372

  日期：2019.8.5

  The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one‐pot reductive amination using pyrrolidine as imine‐formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups

  描述了使用容易获得的Crabtree试剂将环氧化物异构化为醛的方法。使用吡咯烷作为亚胺形成催化剂，通过一锅还原胺化将醛转化为合成有用的胺。该反应在非常温和的条件下以较低的催化剂负载量进行。该过程操作简单，并且可以接受各种功能组。DFT对其机理的研究表明，异构化是通过具有低能垒的氢化铱机理进行的，与温和的反应条件相符。
• Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium
  作者：Timo von Keutz、David Cantillo、C. Oliver Kappe

  DOI：10.1021/acs.orglett.9b04072

  日期：2019.12.20

  preparation of epoxides from ketones has been developed. The method is based on the carefully controlled generation of (bromomethyl)lithium (LiCH2Br) from inexpensive CH2Br2 and MeLi in a continuous flow reactor. The reaction has shown excellent selectivity for a variety of substrates, including α-chloroketones, which typically fail under classic Corey-Chaykovsky conditions. This advantage has been used to develop

  已经开发了从酮直接制备环氧化物的可扩展程序。该方法基于在连续流反应器中从廉价的CH2Br2和MeLi中精心控制的（溴甲基）锂（LiCH2Br）生成。该反应对多种底物（包括α-氯酮）表现出出色的选择性，这些底物通常在经典的Corey-Chaykovsky条件下失效。这一优势已被用于开发一种新的药物氟康唑的途径。
• Retro‐ <i>Corey‐Chaykovsky</i> Epoxidation: Converting Geminal Disubstituted Epoxides to Ketones
  作者：Siqi Li、Pingfan Li、Jiaxi Xu

  DOI：10.1002/hlca.201900164

  日期：2019.9

  epoxidation has been widely applied in the conversion of aldehydes and ketones to epoxides with sulfonium and sulfoxonium ylides. The reverse transformation is realized for conversion of geminal disubstituted epoxides to ketones in the presence of DABCO in refluxing mesitylene. The method is a weak basic transformation from epoxides to ketones with loss of a methylene group and can be applied as an

  Corey-Chaykovsky环氧化已被广泛应用于醛和酮基sulf与醛和酮向环氧化物的转化。在DABCO存在下，在均三甲苯回流中，将双取代的双环氧化物转化为酮可实现反向转化。该方法是从环氧化物到酮的弱碱性转化，但失去了亚甲基，可作为酸催化的Meinwald重排或氧化将环氧化物转化为羰基化合物的替代策略。
• [EN] PYRIDO (4,3-B) INDOLES CONTAINING RIGID MOIETIES<br/>[FR] PYRIDO[4,3-B]INDOLES CONTENANT DES FRAGMENTS RIGIDES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2010051501A1

  公开（公告）日：2010-05-06

  This disclosure is directed to pyrido[4,3-b]indoles having rigid moieties. The compounds in one embodiment are pyrido[4,3-b]indoles having an unsaturated hydrocarbon moiety. The compounds in another embodiment are pyrido[4,3-b]indoles having a cycloalkyl, cycloalkenyl or heterocyclyl moiety. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及具有刚性基团的吡啶并[4,3-b]吲哚化合物。在一个实施例中，这些化合物是具有不饱和碳氢基团的吡啶并[4,3-b]吲哚化合物。在另一个实施例中，这些化合物是具有环烷基、环烯基或杂环基团的吡啶并[4,3-b]吲哚化合物。还提供了包括这些化合物的药物组合物，以及使用这些化合物在各种治疗应用中的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• An air-stable cationic iridium hydride as a highly active and general catalyst for the isomerization of terminal epoxides
  作者：Nicolas Humbert、Devendra J. Vyas、Céline Besnard、Clément Mazet

  DOI：10.1039/c4cc05260a

  日期：——

  We describe the use of an air-stable iridium hydride catalyst for the isomerization of terminal epoxides into aldehydes with perfect regioselectivity.

  我们描述了使用一种空气稳定的铱氢化物催化剂将末端环氧化物异构化为具有完美区域选择性的醛的方法。