3-(diethylaminomethyl)bicyclo[2.2.1]heptan-2-one | 74713-07-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(diethylaminomethyl)bicyclo[2.2.1]heptan-2-one
• CAS: 74713-07-8
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: LRKPMUXYXMDOFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(diethylaminomethyl)bicyclo[2.2.1]heptan-2-one 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以84%的产率得到3-亚甲基-2-降冰片酮
  参考文献：
  名称：

  Dibromomethane as one-carbon source in organic synthesis: microwave-accelerated α-methylenation of ketones with dibromomethane and diethylamine

  摘要：

  The reactivity of aryl alkyl ketone with a preheated mixture of dibromomethane and diethylamine is poor and gives an alpha-methylenation product in very low yield even under refluxing condition. It can be accelerated dramatically by microwave irradiation. Under microwave condition, the cyclic 1,3-dicarbonyls, aryl alkyl ketones, heteroaryl alkyl ketones and acyclic benzyl ketone give alpha-methylenation products in modest to good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00080-2
• 作为产物：
  描述：

  3-亚甲基-2-降冰片酮 、 二乙胺 在 aluminum oxide 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 3-(diethylaminomethyl)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  氧化铝催化的仲胺向环外α，β-不饱和酮的加成反应

  摘要：

  在氧化铝的存在下，已将仲胺迈克尔加成到环外α，β-不饱和酮上，获得了优异的收率。在不存在氧化铝的情况下，经过很长的反应时间后，对于许多副产物，反应不会进行或产率低。

  DOI：

  10.1016/s0040-4039(00)71511-5

文献信息

• Dibromomethane as one-carbon source in organic synthesis: microwave-accelerated α-methylenation of ketones with dibromomethane and diethylamine
  作者：Yung-Son Hon、Tzyy-Rong Hsu、Chun-Yan Chen、Yi-Hui Lin、Fong-Jong Chang、Cheng-Han Hsieh、Ping-Hui Szu

  DOI：10.1016/s0040-4020(03)00080-2

  日期：2003.2

  The reactivity of aryl alkyl ketone with a preheated mixture of dibromomethane and diethylamine is poor and gives an alpha-methylenation product in very low yield even under refluxing condition. It can be accelerated dramatically by microwave irradiation. Under microwave condition, the cyclic 1,3-dicarbonyls, aryl alkyl ketones, heteroaryl alkyl ketones and acyclic benzyl ketone give alpha-methylenation products in modest to good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• An alumina catalyzed addition of secondary amines to exocyclic α,β-unsaturated ketones
  作者：S.William Pelletier、Atanas P. Venkov、Janet Finer-Moore、Naresh V. Mody

  DOI：10.1016/s0040-4039(00)71511-5

  日期：1980.1

  A Michael addition of secondary amines to exocyclic α,β-unsaturated ketones has been achieved in excellent yield in the presence of alumina. In the absence of alumina, the reaction does not proceed or takes place in low yield with many side products after a long reaction time.

  在氧化铝的存在下，已将仲胺迈克尔加成到环外α，β-不饱和酮上，获得了优异的收率。在不存在氧化铝的情况下，经过很长的反应时间后，对于许多副产物，反应不会进行或产率低。