1-cyclopropyl-2-(2-methylphenyl)ethanone | 56594-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-cyclopropyl-2-(2-methylphenyl)ethanone
• 英文别名: 2-Methylbenzyl-cyclopropyl-keton
• CAS: 56594-99-1
• 化学式: C₁₂H₁₄O
• mdl: MFCD11934673
• 分子量: 174.243
• InChiKey: PQVHJDYPNSLCEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-2-(2-methylphenyl)ethanone 在 甲酸铵 作用下， 生成 1-Cyclopropyl-2-(o-tolyl)-ethylamin
  参考文献：
  名称：

  Cussac; Boucherle; Hache, European Journal of Medicinal Chemistry, 1975, vol. 10, # 2, p. 112 - 116

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methylbenzylmagnesium bromide 、 环丙基腈 生成 1-cyclopropyl-2-(2-methylphenyl)ethanone
  参考文献：
  名称：

  Cussac; Boucherle; Hache, European Journal of Medicinal Chemistry, 1975, vol. 10, # 2, p. 112 - 116

  摘要：

  DOI：

文献信息

• Lewis Acid Mediated Reactions of 1-Cyclopropyl-2-arylethanones with Allenic Esters:  A Facile Synthetic Protocol for the Preparation of Dihydrofuro[2,3-<i>h</i>]chromen-2-one Derivatives
  作者：Min Shi、Xiang-Ying Tang、Yong-Hua Yang

  DOI：10.1021/ol701713y

  日期：2007.9.1

  TMSOTf-mediated reactions of 1-cyclopropyl-2-arylethanones with allenic esters afford a novel method for the synthesis of dihydrofuro[2,3-h]chromen-2-one derivatives in moderate to good yields. This process is a sequential reaction involving a nucleophilic ring-opening reaction of the cyclopropane by H(2)O, two intermolecular aldol-type reactions and one intramolecular aldol-type reaction, a cyclic transesterification

  TMSOTf介导的1-环丙基-2-芳基酮与烯丙酸酯的反应提供了一种以中等至良好收率合成二氢呋喃并[2,3-h] chromen-2-one衍生物的新方法。此过程是一个顺序反应，涉及通过H（2）O进行环丙烷的亲核开环反应，两个分子间醇醛型反应和一个分子内醇醛型反应，循环酯交换，脱水和路易斯酸介导的芳构化。
• Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with diethyl 2-oxomalonate and ethyl 2-oxoacetate
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1016/j.tet.2009.09.003

  日期：2009.11

  TMSOTf-mediated reactions of 2-aryl-1-(1-phenylcyclopropyl)ethanones 1 with diethyl 2-oxomalonate 2 afford a novel method for the synthesis of spiro-gamma-lactone derivatives 3 in good to excellent yields via a sequential reaction involving a nucleophilic ring-opening reaction of the cyclopropane by H2O, an aldol-type reaction and a cyclic transesterification mediated by Lewis acid. On the other hand, we found that TMSOTf-mediated reactions of 1-cyclopropyl-2-arylethanones 1 with ethyl 2-oxoacetate 4 could also provide the corresponding spiro-gamma-lactone derivatives 5 in moderate yields along with another spiro-gamma-lactone derivatives 6 derived from the reaction of 1 with two molecules of ethyl 2-oxcracetate. The plausible reaction mechanisms have also been provided on the basis of control experiments. (c) 2009 Elsevier Ltd. All rights reserved.
• Vilsmeier−Haack Reaction of 1-Cyclopropyl-2-arylethanones
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1021/jo801492k

  日期：2008.11.7

  A convenient and efficient method to synthesize 3-(2-chloroethyl)-5-aryl-4H-pyran-4-ones 2 and 2-chloro-3-(2-chloroethyl)-1-naphthaldehydes 3 in moderate to good yields was developed via the Vilsmeier-Haack reaction of readily available 1-cyclopropyl-2-arylethanones 1 at different temperature. This reaction proceeds via sequential enolization, ring opening, haloformylation, and intramolecular nucleophilic cyclization or Friedel-Crafts alkylation reactions to produce 2 or 3.