(1S,2S)-2-Naphthalen-2-yl-cyclopropanecarboxylic acid methoxy-methyl-amide | 134198-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2S)-2-Naphthalen-2-yl-cyclopropanecarboxylic acid methoxy-methyl-amide
• CAS: 134198-12-2
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: FCBHCFAXMXWEBG-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-Naphthalen-2-yl-cyclopropanecarboxylic acid methoxy-methyl-amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 trans-2-(naphthalen-2-yl)cyclopropane-1-carbaldehyde
  参考文献：
  名称：

  Conformationally restricted homotryptamines. Part 4: Heterocyclic and naphthyl analogs of a potent selective serotonin reuptake inhibitor

  摘要：

  A series of hybrid molecules containing the cyclopropylmethylamino side chain found in homotryptamine (1S,2S)-2c and an isosteric heteroaryl or naphthyl core were prepared and their binding affinities for the human serotonin transporter determined. The most potent isosteres were CN-substituted naphthalenes. These results demonstrate that isosteric aromatic cores which lack an H-bond donor site may be substituted for the indole nucleus without substantial loss in hSERT binding. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.083
• 作为产物：
  描述：

  重氮甲烷 、 (E)-N-methoxy-N-methyl-3-(naphthalen-2-yl)acrylamide 在 palladium diacetate 作用下， 生成 (1S,2S)-2-Naphthalen-2-yl-cyclopropanecarboxylic acid methoxy-methyl-amide
  参考文献：
  名称：

  Conformationally restricted homotryptamines. Part 4: Heterocyclic and naphthyl analogs of a potent selective serotonin reuptake inhibitor

  摘要：

  A series of hybrid molecules containing the cyclopropylmethylamino side chain found in homotryptamine (1S,2S)-2c and an isosteric heteroaryl or naphthyl core were prepared and their binding affinities for the human serotonin transporter determined. The most potent isosteres were CN-substituted naphthalenes. These results demonstrate that isosteric aromatic cores which lack an H-bond donor site may be substituted for the indole nucleus without substantial loss in hSERT binding. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.083

文献信息

• A novel route to cyclopropyl ketones, aldehydes, and carboxylic acids.
  作者：Karen E. Rodriques

  DOI：10.1016/s0040-4039(00)79644-4

  日期：1991.3

  Cyclopropanation of α,β-unsaturated N-methoxy-N-methyl amides provided the cyclopropyl amides in far superior yields to those obtained with the corresponding ketones. The desired ketones are then readily accessible by the addition of organometallic reagents. Access to a variety functional groups, including aldehydes and carboxylic acids, is also described.

  α，β-不饱和N-甲氧基-N-甲基酰胺的环丙烷化提供的环丙基酰胺的收率远高于用相应的酮获得的收率。然后通过添加有机金属试剂可以容易地获得所需的酮。还描述了对包括醛和羧酸在内的各种官能团的获取。