(3-(4-chlorophenyl)oxiran-2-yl)(4-methoxyphenyl)methanone | 27547-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-(4-chlorophenyl)oxiran-2-yl)(4-methoxyphenyl)methanone
• 英文别名: 3-(4-chlorophenyl)-2,3-epoxy-4'-methoxypropiophenone；[3-(4-chloro-phenyl)-oxiranyl]-(4-methoxy-phenyl)-methanone；[3-(4-Chlorophenyl)-2-oxiranyl](4-methoxyphenyl)methanone；[3-(4-chlorophenyl)oxiran-2-yl]-(4-methoxyphenyl)methanone
• CAS: 27547-08-6
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: GXXVVGZUYDEJAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (3-(4-chlorophenyl)oxiran-2-yl)(4-methoxyphenyl)methanone 在 三氟化硼乙醚 、 乙二胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanone
  参考文献：
  名称：

  从查耳酮高效合成脱氧安息香

  摘要：

  摘要 通过路易斯酸催化重排由查耳酮环氧化物衍生的 β-酮醛在乙二胺存在下在四氢呋喃 (THF) 中回流时发生平稳的去甲酰化反应，以优异的产率得到脱氧安息香。该方法是通用的，可用于制备具有多种取代模式的脱氧安息香。

  DOI：

  10.1080/00397910601130967
• 作为产物：
  描述：

  4'-methoxy-4-chlorochalcone 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.0h， 以1.3 g的产率得到(3-(4-chlorophenyl)oxiran-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)

  摘要：

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.

  DOI：

  10.1021/jm960803q

文献信息

• [4 + 2] Heterocyclization for Efficient Formation of Substituted Quinoxalines through Carbon-Oxygen Bonds Cleavage
  作者：Man-Su Tu、Hai-Wei Xu、Wei Fan、Bo Jiang、Shu-Jiang Tu

  DOI：10.1002/jhet.2128

  日期：2015.5

  A new domino strategy for efficient synthesis of highly functionalized quinoxaline derivatives via [4 + 2] heterocyclization involving ring‐opening of oxirane process has been developed. The reaction promoted by Cs2CO3 was easy to perform in a simple operation from common and inexpensive starting materials. The bisfunctionalization of quinoxaline framework including C2 benzylation and C3 arylation

  已开发出一种新的多米诺骨牌策略，可通过[4 + 2]杂环化（包括环氧乙烷工艺的开环）有效合成高度官能化的喹喔啉衍生物。由Cs 2 CO 3促进的反应易于由普通且廉价的起始原料以简单的操作进行。喹喔啉骨架的双功能化（包括C2苄基化和C3芳基化）很容易以多米诺骨牌的方式实现，涉及裂解1,3-二芳基-2,3-环氧丙烷-1-酮的三个C-O键。
• One-pot synthesis of chalcone epoxides—A green chemistry strategy
  作者：Dalyna Ngo、Mbelu Kalala、Victoria Hogan、Renuka Manchanayakage

  DOI：10.1016/j.tetlet.2014.06.057

  日期：2014.8

  Waste minimization is a very important aspect of an environmentally benign protocol. A one-pot consec-process has been developed for chalcone epoxide synthesis that allows compounds to be prepared having to isolate and purify the intermediates. The strategy utilizes consecutive Claisen Schmidt and epoxidation reactions to prepare chalcone epoxides from substituted benzaldehydes acetophenones in good yields. (C) 2014 Elsevier Ltd. All rights reserved.
• Visible-Light-Promoted Photoredox Syntheses of α,β-Epoxy Ketones from Styrenes and Benzaldehydes under Alkaline Conditions
  作者：Jing Li、David Zhigang Wang

  DOI：10.1021/acs.orglett.5b02629

  日期：2015.11.6

  A range of styrenes and benzaldehydes were smoothly combined to form alpha,beta-epoxy ketones under the synergistic actions of photocatalyst Ru(bpy)(3)Cl-2, tert-butyl hydroperoxide (t-BuOOH), cesium carbonate (Cs2CO3), and visible light irradiation. The process likely proceeds through visible-light-enabled photocatalytic generations of acyl radicals as key intermediates.
• 1,3,5-TRISUBSTITUTED PYRAZOLE COMPOUNDS FOR TREATMENT OF INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：EP0731796B1

  公开（公告）日：2000-08-02
• US5908852A
  申请人：——

  公开号：US5908852A

  公开（公告）日：1999-06-01