1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-piperidinyl]cyclooctanecarbonitrile | 1032289-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-piperidinyl]cyclooctanecarbonitrile
• 英文别名: 1-(4-(2,5-Dimethyl-1H-pyrrol-1-yl)piperidin-1-yl)cyclooctane-1-carbonitrile；1-[4-(2,5-dimethylpyrrol-1-yl)piperidin-1-yl]cyclooctane-1-carbonitrile
• CAS: 1032289-57-8
• 化学式: C₂₀H₃₁N₃
• 分子量: 313.486
• InChiKey: NCEPBCBCCOAGHX-UHFFFAOYSA-N

物化性质

• 沸点：
  476.4±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-piperidinyl]cyclooctanecarbonitrile 、 甲基溴化镁 以 四氢呋喃 、 二氯甲烷 为溶剂， 以49%的产率得到4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(1-methylcyclooctyl)piperidine
  参考文献：
  名称：

  Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug

  摘要：

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.

  DOI：

  10.1021/jm7012979
• 作为产物：
  描述：

  环辛酮 、 4-(2,5-二甲基-吡咯-1-基)-哌啶 、 氰化钾 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 24.0h， 以72%的产率得到1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-piperidinyl]cyclooctanecarbonitrile
  参考文献：
  名称：

  Convenient Strecker Reactions of Piperidine Derivatives with Cyclic Ketones under Aqueous Conditions

  摘要：

  Strecker reactions convenient for the preparation of piperidinyl acetonitrile compounds under aqueous conditions are described. The use of TsOH center dot H2O is the key to afford the desired products in good and reproducible yield.

  DOI：

  10.1080/00397910701845795

文献信息

• Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3<i>R</i>)-3-piperidinyl]-1<i>H</i>-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug
  作者：Shigeo Hayashi、Akiko Hirao、Aki Imai、Hiroshi Nakamura、Yoshinori Murata、Katsuyo Ohashi、Eriko Nakata

  DOI：10.1021/jm7012979

  日期：2009.2.12

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.
• Convenient Strecker Reactions of Piperidine Derivatives with Cyclic Ketones under Aqueous Conditions
  作者：Yoshinori Murata、Kunio Satake

  DOI：10.1080/00397910701845795

  日期：2008.4

  Strecker reactions convenient for the preparation of piperidinyl acetonitrile compounds under aqueous conditions are described. The use of TsOH center dot H2O is the key to afford the desired products in good and reproducible yield.