(3-(4-methoxyphenyl)oxiran-2-yl)(p-tolyl)methanone | 32383-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-(4-methoxyphenyl)oxiran-2-yl)(p-tolyl)methanone
• 英文别名: (2RS,3SR)-2,3-epoxy-3-(4-methoxyphenyl)-1-(4-methylphenyl)propan-1-one；[(2S,3R)-3-(4-methoxyphenyl)oxiran-2-yl]-(4-methylphenyl)methanone
• CAS: 32383-87-2
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: DTJXZSSJZDLWGV-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-3-(4-甲氧基苯基)-1-(4-甲基苯基)-2-丙烯-1-酮 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 以99%的产率得到(3-(4-methoxyphenyl)oxiran-2-yl)(p-tolyl)methanone
  参考文献：
  名称：

  Adam, Waldemar; Hadjiarapoglou, Lazaros; Smerz, Alex, Chemische Berichte, 1991, vol. 124, # 1, p. 227 - 232

  摘要：

  DOI：

文献信息

• One-pot synthesis of α,β-epoxy ketones through domino reaction between alkenes and aldehydes catalyzed by proline based chiral organocatalysts
  作者：Veeramanoharan Ashokkumar、Ayyanar Siva

  DOI：10.1039/c7ob00031f

  日期：——

  Proline based metal free organocatalysts were developed by using a new approach for the synthesis of epoxide derivatives through a domino reaction. This domino reaction (oxidative coupling) allows a direct access to epoxides from various alkenes and aldehydes through C–H functionalization and C–C/C–O bond formation. The catalytic efficiencies of the newly synthesized organocatalysts were also determined

  通过使用一种通过多米诺反应合成环氧化物衍生物的新方法，开发了基于脯氨酸的无金属有机催化剂。这种多米诺反应（氧化偶联）允许通过C–H功能化和C–C / C–O键形成直接从各种烯烃和醛中获得环氧化物。还通过多米诺反应在含有醛和烯烃衍生物的各种官能团的存在下通过多米诺反应测定了新合成的有机催化剂的催化效率，产率很高（高达95％），ee的产率高达99％。
• Oxidative Coupling of Alkenes with Aldehydes and Hydroperoxides: One-Pot Synthesis of 2,3-Epoxy Ketones
  作者：Wen-Ting Wei、Xu-Heng Yang、Hai-Bing Li、Jin-Heng Li

  DOI：10.1002/adsc.201400629

  日期：2015.1.12

  A new transition metal‐free oxidative coupling of unactivated terminal alkenes with aldehydes and hydroperoxides in the presence of 10 mol% potassium tert‐butanolate (t‐BuOK) is described thereby realizing trifunctionalization of alkenes toward 2,3‐epoxy ketones. This method is applicable to a wide range of aldehydes, including aryl and alkyl aldehydes, with excellent functional group tolerance, and

  描述了在10摩尔％叔丁醇钾（t- BuOK）存在下，未活化的末端烯烃与醛和氢过氧化物的新的无过渡金属的氧化偶联，从而实现了烯烃向2,3-环氧酮的三官能化。该方法适用于广泛的醛类，包括芳基和烷基醛，具有出色的官能团耐受性，并且可一步一步组装2,3-环氧酮。
• Adam, Waldemar; Hadjiarapoglou, Lazaros; Smerz, Alex, Chemische Berichte, 1991, vol. 124, # 1, p. 227 - 232
  作者：Adam, Waldemar、Hadjiarapoglou, Lazaros、Smerz, Alex

  DOI：——

  日期：——
• Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
  作者：Sylvie Ducki、David Rennison、Meiko Woo、Alexander Kendall、Jérémie Fournier Dit Chabert、Alan T. McGown、Nicholas J. Lawrence

  DOI：10.1016/j.bmc.2009.09.039

  日期：2009.11

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.