(4-methoxyphenyl)(3-p-tolyloxiran-2-yl)methanone | 32383-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-methoxyphenyl)(3-p-tolyloxiran-2-yl)methanone
• 英文别名: (2RS,3SR)-2,3-epoxy-1-(4-methoxyphenyl)-3-(4-methylphenyl)propan-1-one；(4-methoxyphenyl)-[(2S,3R)-3-(4-methylphenyl)oxiran-2-yl]methanone
• CAS: 32383-88-3
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: ZWEVSAWMQRODSL-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

• 作为反应物：
  描述：

  盐酸胍 、 (4-methoxyphenyl)(3-p-tolyloxiran-2-yl)methanone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到2-amino-4-(4-methoxyphenyl)-4-[(4-methylphenyl)methyl]-1H-imidazol-5-one
  参考文献：
  名称：

  2,3-环氧二芳基酮的新型一锅重排反应：(±)-5,5-二取代咪唑酮和5,5-二取代乙内酰脲的合成

  摘要：

  在氢化钠等碱和新型咪唑酮衍生物存在下，用盐酸胍或尿素处理 2,3-环氧二苯基酮时，发生了一种新的一锅重排反应，包括顺序环氧化物重排、缩合、环化和苯基迁移以良好到极好的收率获得。

  DOI：

  10.1055/s-2006-950277
• 作为产物：
  描述：

  (E)-1-(4-methoxyphenyl)-3-p-tolylprop-2-en-1-one 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83%的产率得到(4-methoxyphenyl)(3-p-tolyloxiran-2-yl)methanone
  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

• 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。
• A Novel One-Pot Rearrangement Reaction of 2,3-Epoxydiaryl Ketones: Synthesis of (±)-5,5-Disubstituted Imidazolones and 5,5-Disubstituted Hydantoins
  作者：Kanaya Dhar、Bilal Bhat、Satish Puri、Michael Spiteller

  DOI：10.1055/s-2006-950277

  日期：2006.10

  A novel one-pot rearrangement reaction, involving sequential epoxide rearrangement, condensation, cyclization and phenyl migration took place when 2,3-epoxydiphenyl ketones were treated with guanidine hydrochloride or urea in the presence of a base like sodium hydride and new type of imidazolone derivatives were obtained in good to excellent yields.

  在氢化钠等碱和新型咪唑酮衍生物存在下，用盐酸胍或尿素处理 2,3-环氧二苯基酮时，发生了一种新的一锅重排反应，包括顺序环氧化物重排、缩合、环化和苯基迁移以良好到极好的收率获得。
• 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.