2-(4-methylphenyl)-1-cyclopropylethan-1-one | 56594-97-9

• 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: 2-(4-methylphenyl)-1-cyclopropylethan-1-one
• 英文别名: 1-cyclopropyl-2-(4-methylphenyl)ethanone；1-cyclopropyl-2-(p-tolyl)ethanone；4-Methylbenzyl-cyclopropyl-keton；1-Cyclopropyl-2-(4-methylphenyl)ethan-1-one
• CAS: 56594-97-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: GSYKTUSATKARAM-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：
  0.42
• 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：

  2-(4-methylphenyl)-1-cyclopropylethan-1-one 在 甲酸铵 作用下， 生成 1-<(2-Cyanethyl)-amino>-2-(p-tolyl)-1-cyclopropyl-ethan
  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：

  magnesium,1-methanidyl-4-methylbenzene,bromide 、 环丙基腈 生成 2-(4-methylphenyl)-1-cyclopropylethan-1-one
  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

• Palladium-Catalyzed Mono-α-Arylation of Acetone with Aryl Imidazolylsulfonates
  作者：Lutz Ackermann、Vaibhav P. Mehta

  DOI：10.1002/chem.201201394

  日期：2012.8.13

  Set the ace(tone): A palladium catalyst derived from the bidentate XantPhos ligand and Pd(OAc)2 has enabled broadly applicable mono‐α‐arylations of acetone to be performed with air‐ and moisture‐stable aryl imidazolylsulfonates as most user‐friendly electrophiles (see scheme).

  设定ace（tone）：一种由双齿XantPhos配体和Pd（OAc）2衍生的钯催化剂，使得最广泛使用的丙酮单α-芳基化反应可以与空气和水分稳定的芳基咪唑基磺酸盐一起使用，这是最易于使用的亲电试剂（请参阅方案）。
• Lewis Acid-Mediated Reactions of 1-Cyclopropyl-2-arylethanone Derivatives with Allenic Ester, Ethyl Acetoacetate, and Methyl Acrylate
  作者：Min Shi、Xiang-Ying Tang、Yong-Hua Yang

  DOI：10.1021/jo800608h

  日期：2008.7.1

  TMSOTf-mediated reactions of 2-aryl-1-(1-phenylcyclopropyl)ethanones 1 with allenic esters afford a novel method for the synthesis of 6-methyl-3a,7-diaryl-3,3a-dihydro-2H-benzofuran-4-one derivatives 2 in moderate yields. In addition, we also found that TMSOTf-mediated reactions of 1-cyclopropyl-2-arylethanones with ethyl acetoacetate can provide the corresponding 2,3-dihydrobenzofuran-4-ol and dihydrofuro[2

  TMSOTf介导的2-芳基-1-（1-苯基环丙基）乙炔酮1与烯丙酸酯的反应为合成6-甲基-3a，7-二芳基-3,3a-二氢-2 H-苯并呋喃-提供了一种新方法4-一衍生物2的产率中等。此外，我们还发现，TMSOTf介导的1-环丙基-2-芳基蒽酮与乙酰乙酸乙酯的反应可提供相应的2,3-二氢苯并呋喃-4-醇和二氢呋喃[2,3 - h ]铬-2-酮通过涉及H 2的环丙烷的亲核开环反应的顺序反应获得中等收率O，一个分子间的醇醛型反应和两个分子内的醇醛型反应，循环酯交换，脱水和芳构化。而且，通过使用丙烯酸甲酯代替烯丙酸酯，相应的7-芳基-3,5,6,7-四氢-2 H-苯并呋喃-4-酮和5-芳基-3,5,6,7-四氢-在Bi（OTf）2 Cl存在下，可以中等至高产率形成2 H-苯并呋喃-4-酮。在控制实验的基础上，还提供了合理的反应机理。
• 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。
• Substituted pyrimidines as aurora kinase inhibitors
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP2292614A1

  公开（公告）日：2011-03-09

  The present invention provides a facile process for the preparation of tri- and tetra-substituted pyrimidines. The process is useful for preparing inhibitors of protein kinases, especially Aurora kinase. These inhibitors are useful for treating or lessening the severity of Aurora-mediated diseases or conditions.

  本发明提供了一种制备三取代和四取代嘧啶的简便工艺。该工艺可用于制备蛋白激酶，特别是极光激酶的抑制剂。这些抑制剂可用于治疗或减轻 Aurora 介导的疾病或病症的严重程度。
• 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.