(2RS,3SR)-2,3-epoxy-1-(4-methylphenyl)-3-(4-methylphenyl)propan-1-one | 32383-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2RS,3SR)-2,3-epoxy-1-(4-methylphenyl)-3-(4-methylphenyl)propan-1-one
• 英文别名: p-tolyl(3-p-tolyloxiran-2-yl)methanone；(4-methylphenyl)-[(2S,3R)-3-(4-methylphenyl)oxiran-2-yl]methanone
• CAS: 32383-89-4
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: CVIUROKVZKDVJK-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-2,3-epoxy-1-(4-methylphenyl)-3-(4-methylphenyl)propan-1-one 在 对甲苯磺酸 、 一水合肼 作用下， 以 xylene 为溶剂， 反应 3.0h， 生成 3,5-双(4-甲基苯基)-1H-吡唑
  参考文献：
  名称：

  Monoamine Oxidase Isoform-Dependent Tautomeric Influence in the Recognition of 3,5-Diaryl Pyrazole Inhibitors

  摘要：

  A series of 3,5-diaryl pyrazoles were prepared and assayed for their ability to inhibit reversibly monoamine oxidase-A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds show inhibitory activity with concentration values in the nanomolar range. A computational work was carried out on the two most selective inhibitors that have tautomeric pyrazole forms. The binding free energies of these compounds for each MAO isoform were influenced by the tautomeric equilibria.

  DOI：

  10.1021/jm060868l
• 作为产物：
  描述：

  trans-4,4'-dimethylchalcone 在 叔丁基过氧化氢 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 为溶剂， 以62%的产率得到(2RS,3SR)-2,3-epoxy-1-(4-methylphenyl)-3-(4-methylphenyl)propan-1-one
  参考文献：
  名称：

  Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.09.039

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％。
• Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe₃)₂]₃with chiral TADDOL ligands
  作者：Haiwen Shan、Chengrong Lu、Bei Zhao、Yingming Yao

  DOI：10.1039/d0nj05228k

  日期：——

  The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that the combination of Yb[N(SiMe3)2]3 and chiral TADDOL ligand H2L2 ((4S,5S)-2,2-dimethyl-α,α,α′,α′-tetra-3,5-bis(trifluormethylphenyl)-1,3-dioxolane-4

  α的催化不对称环氧化，通过β不饱和酮叔-butylhydroperoxide（TBHP）已经很好地使用稀土类金属酰胺建立RE [N（森达3）2 ] 3（RE = La（上1），钕（2） ，Sm（3），Y（4），Yb（5））和手性TADDOL配体。发现Yb [N（SiMe 3）2 ] 3和手性TADDOL配体H 2 L 2（（4 S，5 S）摩尔比为1：1的）-2,2-二甲基-α，α，α'，α'-tetra-3,5-双（三氟甲基苯基）-1,3-二氧戊环-4,5-二甲醇）最佳选择，使用DBU作为添加剂，可以以优异的收率（89–99％）和良好至高的对映选择性（57–94％ee）提供所需的环氧化物。各种底物被证明具有官能团耐受性。此外，还进行了克级实验和衍生化实验。
• 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。
• Regio- and Stereoselective Reaction of α-Epoxyketones with AlCl₃: An Efficient Approach for the Synthesis of Functionalized β-Chlorohydrines
  作者：Farzad Nikpour、Roya Mozafari、Baran Mohammadi Mogaddam

  DOI：10.1002/jccs.200900059

  日期：2009.4

  A simple and efficient synthesis of functionalized β‐chlorohydrins is described from the regio‐ and stereoselective reaction of α‐epoxyketones with AlCl3 in acetonitrile at room temperature.

  在室温下，乙炔中α-环氧酮与AlCl 3的区域和立体选择性反应描述了一种简单有效的功能化β-氯醇的合成方法。
• 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：——