1,2-epoxy-3-(m-methoxyphenyl)propane | 74769-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-epoxy-3-(m-methoxyphenyl)propane
• 英文别名: (+/-)-1,2-Epoxy-3-<3-methoxy-phenyl>-propan；1,2-epoxy-3-(3-methoxy-phenyl)-propane；1,2-Epoxy-3-(3-methoxy-phenyl)-propan；2-(3-Methoxybenzyl)oxirane；2-[(3-methoxyphenyl)methyl]oxirane
• CAS: 74769-16-7
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: QIRCLNOOFJHRDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  148-150 °C(Press: 7.8 Torr)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 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：

  1,2-epoxy-3-(m-methoxyphenyl)propane 在 2,4,6-三异丙基苯磺酰叠氮化物 、 Rh₂(α,α,α',α'-tetramethyl-1,3-benzenedipropionate)₂ 、 碘 、 magnesium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过碘酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 乙腈 为溶剂， 反应 1.25h， 生成 2-(3-methoxyphenyl)-3,3-dimethylcyclohexanone
  参考文献：
  名称：

  Cyclohexanones by Rh-Mediated Intramolecular C–H Insertion

  摘要：

  Some long chain alpha-aryl alpha-diazo ketones under Rh catalysis cyclize efficiently to the corresponding cyclohexanones. This is in marked contrast to the cyclizations of alpha-diazo beta-ketoesters, which consistently deliver cyclopentanone products.

  DOI：

  10.1021/jo4014996
• 作为产物：
  描述：

  3-(3-甲氧基苯基)-1-丙烯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到1,2-epoxy-3-(m-methoxyphenyl)propane
  参考文献：
  名称：

  Acyclic analogs of 2-(4-phenylpiperidino)cyclohexanol (vesamicol): conformationally mobile inhibitors of vesicular acetylcholine transport

  摘要：

  Several 1,3-disubstituted propan-2-ols and one alpha,beta-disubstituted ethanol (11i) were synthesized and evaluated as potential acyclic mimics of the vesicular acetylcholine transport inhibitor 2-(4-phenylpiperidinyl)cyclohexanol (1, vesamicol, AH5183). Analogues containing the 4-phenylpiperidyl fragment (11a, 11b) were more potent than those containing the 4-phenylpiperazyl moiety (11e, 11f). Substitution at the second terminal carbon of the propyl (or ethyl) fragment with simple lipophilic aryl substituents yielded potent inhibitors of vesicular acetylcholine storage, including (-)-11a and d-11i, which are equipotent with vesamicol. However, the activity of analogues containing bicyclic aryl groups was susceptible to aryl substitution patterns (11g vs 11h), indicating a definite receptor site topography. In addition, the inhibitory activity of these acyclic analogues was enantioselective, exhibiting a preference, similar to the parent vesamicol, for the levorotatory isomer [(-)-11a vs (+)-11a]. Therefore, the simple lipophilic acyclic vicinal amino alcohols may successfully mimic the biological activity of vesamicol.

  DOI：

  10.1021/jm00112a044

文献信息

• Nickel-catalyzed cross-coupling of epoxides with aryltriflates: rapid and regioselective construction of aryl ketones
  作者：Jinglin Qu、Zijuan Yan、Xuchao Wang、Jun Deng、Feipeng Liu、Zi-Qiang Rong

  DOI：10.1039/d2cc02891c

  日期：——

  biologically active molecules and functional materials. Presented herein is a facile synthetic method for the construction of ketones via Ni-catalyzed cross coupling of epoxides with aryltriflates. A range of easily accessible epoxides can be highly regioselectively converted to the corresponding aryl ketones with good yields in a redox neutral fashion.

  芳基酮是一类最重要的有机化合物，广泛存在于各种药理化合物、生物活性分子和功能材料中。本文介绍了一种通过Ni 催化的环氧化物与芳基三氟甲磺酸酯的交叉偶联来构建酮的简便合成方法。一系列易于获得的环氧化物可以高度区域选择性地转化为相应的芳基酮，并以氧化还原中性方式以良好的收率。
• Watanabe, Journal of the Agricultural Chemical Society of Japan, 1959, vol. 23, p. 257
  作者：Watanabe

  DOI：——

  日期：——
• Friedel-Crafts cyclialkylations of some epoxides
  作者：Stephen K. Taylor、Gregory H. Hockerman、Gregory L. Karrick、Stephen B. Lyle、Scott B. Schramm

  DOI：10.1021/jo00163a001

  日期：1983.7
• 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..
• Acyclic analogs of 2-(4-phenylpiperidino)cyclohexanol (vesamicol): conformationally mobile inhibitors of vesicular acetylcholine transport
  作者：S. M. N. Efange、R. H. Michelson、A. K. Dutta、S. M. Parsons

  DOI：10.1021/jm00112a044

  日期：1991.8

  Several 1,3-disubstituted propan-2-ols and one alpha,beta-disubstituted ethanol (11i) were synthesized and evaluated as potential acyclic mimics of the vesicular acetylcholine transport inhibitor 2-(4-phenylpiperidinyl)cyclohexanol (1, vesamicol, AH5183). Analogues containing the 4-phenylpiperidyl fragment (11a, 11b) were more potent than those containing the 4-phenylpiperazyl moiety (11e, 11f). Substitution at the second terminal carbon of the propyl (or ethyl) fragment with simple lipophilic aryl substituents yielded potent inhibitors of vesicular acetylcholine storage, including (-)-11a and d-11i, which are equipotent with vesamicol. However, the activity of analogues containing bicyclic aryl groups was susceptible to aryl substitution patterns (11g vs 11h), indicating a definite receptor site topography. In addition, the inhibitory activity of these acyclic analogues was enantioselective, exhibiting a preference, similar to the parent vesamicol, for the levorotatory isomer [(-)-11a vs (+)-11a]. Therefore, the simple lipophilic acyclic vicinal amino alcohols may successfully mimic the biological activity of vesamicol.