N-(6-Methoxy-indan-1-ylmethyl)-propionamide | 220547-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-(6-Methoxy-indan-1-ylmethyl)-propionamide
• 英文别名: N-[(6-methoxy-2,3-dihydro-1H-inden-1-yl)methyl]propanamide
• CAS: 220547-07-9
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: FIZDNHSEMRVWSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(6-Methoxy-indan-1-ylmethyl)-propionamide 生成 N-(6-methoxy-indan-1-ylmethyl)-propionamide
  参考文献：
  名称：

  Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors

  摘要：

  Benzocycloalkane derivatives 1-4 were synthesized as new conformationally restricted melatoninergic ligands. They were prepared by rite reaction of the ketones 5 with diethylcyanophosphonate and the reduction of the corresponding cyano compounds or by the Wittig reaction and Curtius degradation to obtain the amines 8. The 1-Cyanobenzocyclobutane derivative was obtained by the benzyne cyclisation reaction. The amines 8 were acylated with acetyl, propionyl or butyryl groups. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand The indanyl (2b,c) tetralin (3a-c) and benzocycloheptane (4c) derivatives were potent compounds with nanomolar affinity and an important enantioselectivity of the receptor was observed with the (+) enantiomers 2b and 3b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00601-5
• 作为产物：
  描述：

  6-甲氧基-1-茚酮 在 镍 ammonium hydroxide 、 sodium tetrahydroborate 、 甲烷磺酸 、 锂丁酯 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 N-(6-Methoxy-indan-1-ylmethyl)-propionamide
  参考文献：
  名称：

  Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors

  摘要：

  Benzocycloalkane derivatives 1-4 were synthesized as new conformationally restricted melatoninergic ligands. They were prepared by rite reaction of the ketones 5 with diethylcyanophosphonate and the reduction of the corresponding cyano compounds or by the Wittig reaction and Curtius degradation to obtain the amines 8. The 1-Cyanobenzocyclobutane derivative was obtained by the benzyne cyclisation reaction. The amines 8 were acylated with acetyl, propionyl or butyryl groups. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand The indanyl (2b,c) tetralin (3a-c) and benzocycloheptane (4c) derivatives were potent compounds with nanomolar affinity and an important enantioselectivity of the receptor was observed with the (+) enantiomers 2b and 3b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00601-5

文献信息

• Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors
  作者：S. Kloubert、M. Mathé-Allainmat、J. Andrieux、S. Sicsic、M. Langlois

  DOI：10.1016/s0960-894x(98)00601-5

  日期：1998.12

  Benzocycloalkane derivatives 1-4 were synthesized as new conformationally restricted melatoninergic ligands. They were prepared by rite reaction of the ketones 5 with diethylcyanophosphonate and the reduction of the corresponding cyano compounds or by the Wittig reaction and Curtius degradation to obtain the amines 8. The 1-Cyanobenzocyclobutane derivative was obtained by the benzyne cyclisation reaction. The amines 8 were acylated with acetyl, propionyl or butyryl groups. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand The indanyl (2b,c) tetralin (3a-c) and benzocycloheptane (4c) derivatives were potent compounds with nanomolar affinity and an important enantioselectivity of the receptor was observed with the (+) enantiomers 2b and 3b. (C) 1998 Elsevier Science Ltd. All rights reserved.