3,4,5,6-tetrahydro-9-nitro-4-(2-propenyl)-2H-1,5-methano-1,4-benzodiazocine | 80770-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,4,5,6-tetrahydro-9-nitro-4-(2-propenyl)-2H-1,5-methano-1,4-benzodiazocine
• 英文别名: 4-allyl-9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine；4-nitro-10-prop-2-enyl-1,10-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene
• CAS: 80770-24-7
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: XEITVRVHAATQFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,5,6-tetrahydro-9-nitro-2H-1,5-methano-1,4-benzodiazocine 、 3-溴丙烯 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,4,5,6-tetrahydro-9-nitro-4-(2-propenyl)-2H-1,5-methano-1,4-benzodiazocine
  参考文献：
  名称：

  Synthesis and antinociceptive activity of 4-(cyclopropylmethyl)-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocin-9-amine and congeners

  摘要：

  The synthesis of 1,4-benzodiazocines has been extended to include the 9-amines. The title compound, 6, was prepared from the known nor-base by N-acylation with cyclopropanecarboxylic acid anhydride, followed by nitration of the aromatic ring and sequential reduction of the resulting nitroamide. Standard in vivo bioassays for antinociceptive and opiate antagonist activities indicated that 6 is an analgesic agonist mixed narcotic antagonist whose oral to parenteral activity ratio approaches unity. Resolution of 6 established that the activity of the racemate resides in the dextrorotatory antipode. Several congeners were also prepared and tested. Their synthesis and structure-activity relationships are given in this paper.

  DOI：

  10.1021/jm00383a007

文献信息

• 1,5-Methano-1,4-benzodiazocines, intermediates therefor, and method of
  申请人：Sterling Drug Inc.

  公开号：US04299830A1

  公开（公告）日：1981-11-10

  4-Q-9-RR'N-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocines wherein Q is propyl, isobutyl, neopentyl, allyl, 2-methyl-2-propenyl, 2-chloro-2-propenyl, cis-3-chloro-2-propenyl, cis-3-chloro-2-butenyl, trans-3-chloro-2-butenyl, propargyl, cyclopropylmethyl or (2,2-dichlorocyclopropyl)methyl; and R and R' are both hydrogens or both methyls; or R is hydrogen and R' is methyl, ethyl, propyl, butyl, isobutyl or benzyl and acid addition salts thereof are useful as strong analgesics and are prepared from the known 3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine by multi-step processes including acylation (including acetylation), nitration, nitro reduction, amide reduction, deacetylation, alkylation and dimethylation.

  4-Q-9-RR'N-3,4,5,6-四氢-2H-1,5-甲基-1,4-苯并二氮杂环中，其中Q为丙基、异丁基、新戊基、烯丙基、2-甲基-2-丙烯基、2-氯-2-丙烯基、顺-3-氯-2-丙烯基、顺-3-氯-2-丁烯基、反-3-氯-2-丁烯基、丙炔基、环丙甲基或（2,2-二氯环丙基）甲基；R和R'均为氢或甲基；或R为氢，而R'为甲基、乙基、丙基、丁基、异丁基或苄基。这些化合物的酸盐加成物可用作强烈止痛药，并通过多步反应制备自已知的3,4,5,6-四氢-2H-1,5-甲基-1,4-苯并二氮杂环，包括酰化（包括乙酰化）、硝化、硝基还原、酰胺还原、脱乙酰、烷基化和二甲基化。
• US4299830A
  申请人：——

  公开号：US4299830A

  公开（公告）日：1981-11-10
• Synthesis and antinociceptive activity of 4-(cyclopropylmethyl)-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocin-9-amine and congeners
  作者：Franklyn W. Gubitz

  DOI：10.1021/jm00383a007

  日期：1985.6

  The synthesis of 1,4-benzodiazocines has been extended to include the 9-amines. The title compound, 6, was prepared from the known nor-base by N-acylation with cyclopropanecarboxylic acid anhydride, followed by nitration of the aromatic ring and sequential reduction of the resulting nitroamide. Standard in vivo bioassays for antinociceptive and opiate antagonist activities indicated that 6 is an analgesic agonist mixed narcotic antagonist whose oral to parenteral activity ratio approaches unity. Resolution of 6 established that the activity of the racemate resides in the dextrorotatory antipode. Several congeners were also prepared and tested. Their synthesis and structure-activity relationships are given in this paper.