3-(quinolin-3-yl)-cyclohex-2-enone | 1107641-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(quinolin-3-yl)-cyclohex-2-enone
• 英文别名: 3-Quinolin-3-ylcyclohex-2-en-1-one
• CAS: 1107641-11-1
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: MHZUOGBQJPEUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 2-环己烯-1-酮 在 potassium fluoride 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以59%的产率得到3-(quinolin-3-yl)-cyclohex-2-enone
  参考文献：
  名称：

  Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one

  摘要：

  The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentanones or 3-arylcyclohexanones as side-products. Using KF as base, DMF as solvent and Pd(OAc)(2) as catalyst, the target products were obtained in moderate to good yields with a variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, acetyl, benzoyl, formyl, ester or nitrile on the aryl bromide are tolerated. Sterically congested aryl bromides or bromopyridines can also be employed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.006

文献信息

• Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one
  作者：Yacoub Fall、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tet.2008.11.006

  日期：2009.1

  The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentanones or 3-arylcyclohexanones as side-products. Using KF as base, DMF as solvent and Pd(OAc)(2) as catalyst, the target products were obtained in moderate to good yields with a variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, acetyl, benzoyl, formyl, ester or nitrile on the aryl bromide are tolerated. Sterically congested aryl bromides or bromopyridines can also be employed. (C) 2008 Elsevier Ltd. All rights reserved.