ethyl 7-iodomethyl-8-oxo-5,6,7,8-tetrahydroquinoline-7-carboxylate | 864499-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 7-iodomethyl-8-oxo-5,6,7,8-tetrahydroquinoline-7-carboxylate
• 英文别名: Ethyl 7-(iodomethyl)-8-oxo-5,6-dihydroquinoline-7-carboxylate
• CAS: 864499-16-1
• 化学式: C₁₃H₁₄INO₃
• 分子量: 359.164
• InChiKey: ZDUXGRXDKKDKRL-UHFFFAOYSA-N

物化性质

• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.644±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 7-iodomethyl-8-oxo-5,6,7,8-tetrahydroquinoline-7-carboxylate 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 以58%的产率得到ethyl 9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-7-carboxylate
  参考文献：
  名称：

  A Novel Class of Cycloalkano[b]pyridines as Potent and Orally Active Opioid Receptor-like 1 Antagonists with Minimal Binding Affinity to the hERG K⁺Channel

  摘要：

  A series of compounds based on 7-{[4-(2-methylphenyl)piperidin-1-yl]methyl}-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-9-ol ((-)-8b), a potent and selective opioid receptor-like 1 (ORL1) antagonist, was prepared and evaluated using structure-activity relationship studies with the aim of removing its affinity to human ether-a-go-go related gene (hERG) K+ channel. From these studies, 10l was identified as an optimized structure with respect to ORL1 antagonist activity, and affinity to the hERG K+ channel. Furthermore, 10l showed good in vivo antagonism with a wide therapeutic index in regards to adverse cardiovascular effects.

  DOI：

  10.1021/jm701590h
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉 在 吡啶 、 碘 、 sodium hydride 、 potassium hydrogencarbonate 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸酐 为溶剂， 反应 45.5h， 生成 ethyl 7-iodomethyl-8-oxo-5,6,7,8-tetrahydroquinoline-7-carboxylate
  参考文献：
  名称：

  EP1726590

  摘要：

  公开号：

文献信息

• An Efficient and Convenient Synthesis of Tetrahydrocycloheptapyridines: New Precursors for CNS Agents
  作者：Takashi Yoshizumi、Hiroshi Miyazoe、Yuichi Sugimoto、Hirobumi Takahashi、Osamu Okamoto

  DOI：10.1055/s-2005-865306

  日期：——

  Development of a convenient and efficient synthetic route for functionalized tetrahydrocycloheptapyridines was accomplished by stepwise iodomethylation and subsequent radical ring expansion using a Bu 3 SnH/AIBN reaction system. Thus, 8- or 5-oxotetrahydroquinolines 4a and 4d and 8- or 5-oxotetrahydroiso-quinolines 4b and 4c afforded the 5,6,7,8-tetrahydrocycloheptapyridine-9-ones 3a and 3d and 6,7

  通过逐步碘甲基化和随后使用 Bu 3 SnH/AIBN 反应体系进行自由基扩环，开发了一种方便有效的官能化四氢环庚吡啶合成路线。因此，8-或 5-氧代四氢喹啉 4a 和 4d 以及 8-或 5-氧代四氢异喹啉 4b 和 4c 得到 5,6,7,8-四氢环庚吡啶-9-酮 3a 和 3d 以及 6,7,8,9-四氢环庚吡啶-5-酮 3b 和 3c，分别以中等总产率 (37-61%)。还发现该反应序列适用于其他杂环稠环庚酮的制备。
• Cycloalkanopyridine derivative
  申请人：Takahashi Hirobumi

  公开号：US20070191419A1

  公开（公告）日：2007-08-16

  Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.

  提供的是式[I]的环烷基吡啶衍生物：[其中符号与说明中所述相同]。这些化合物作为一种nociceptin受体拮抗剂，可用作与nociceptin受体相关的疾病的药物，例如作为缓解对麻醉镇痛剂的耐受性的药物；对麻醉镇痛剂的依赖或成瘾的缓解剂；镇痛增强剂；抗肥胖或食欲抑制剂；治疗或预防认知障碍和失忆症的药物；治疗发育性认知异常的药物；治疗精神分裂症的药物；治疗神经退行性疾病的药物；抗抑郁或治疗情感障碍的药物；治疗或预防尿崩症的药物；治疗或预防多尿症的药物；或治疗低血压的药物。
• CYCLOALKANOPYRIDINE DERIVATIVE
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1726590A1

  公开（公告）日：2006-11-29

  Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.

  所提供的是式[I]的环烷吡啶衍生物： [其中符号与描述中的符号相同]。这些化合物具有痛觉素受体拮抗剂的作用，可作为治疗与痛觉素受体相关疾病的药物，例如，可作为麻醉镇痛剂耐受性的缓解剂；麻醉镇痛剂依赖或成瘾的缓解剂；镇痛增强剂；抗厌食或食欲抑制剂；治疗或预防认知障碍和痴呆/失忆症的药物；治疗发育性认知异常的药物；治疗精神分裂症的药物；治疗神经退行性疾病的药物；抗抑郁剂或治疗情感障碍的药物；治疗或预防糖尿病性尿崩症的药物；治疗或预防多尿症的药物；或治疗低血压的药物。
• US7855294B2
  申请人：——

  公开号：US7855294B2

  公开（公告）日：2010-12-21