azacyclooctano<2,1-b>-4(3H)-quinazolinone | 58314-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: azacyclooctano<2,1-b>-4(3H)-quinazolinone
• 英文别名: 8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-one；6,7,8,9,10,11-hexahydro-azocino[2,1-b]quinazolin-13-one；6,7,8,9,10,11-Hexahydro-13h-azocino[2,1-b]quinazolin-13-one；6,7,8,9,10,11-hexahydroazocino[2,1-b]quinazolin-13-one
• CAS: 58314-97-9
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: RJDGOLWDHKFBOF-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  386.1±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)
• 保留指数：
  2181

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  azacyclooctano<2,1-b>-4(3H)-quinazolinone 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以74%的产率得到6,7,8,9,10,11-hexahydroazepino[2,1-b]quinazoline-12(6H)-thione
  参考文献：
  名称：

  新型三环喹唑啉亚胺和相关的四环氮桥头化合物作为胆碱酯酶抑制剂，对丁酰胆碱酯酶具有选择性。

  摘要：

  合成了四环氮桥头化合物，二苯并二氮杂胺和三环喹唑啉亚胺，其中脂环环系统的大小以及喹唑啉亚胺部分和与亚胺氮原子相连的苯环之间的烷基链的长度被系统地改变，并且它们具有分别评估了乙酰胆碱酯酶和丁酰胆碱酯酶（AChE / BChE）的抑制作用。与加兰他敏和卡巴拉汀相比，已鉴定出中度和强效BChE抑制剂，它们对混合BChE表现出混合的亲和力或中度或高度选择性。

  DOI：

  10.1016/j.bmc.2005.10.044
• 作为产物：
  描述：

  2-叠氮苯甲酸 在 氯化亚砜 、 三丁基膦 、 三乙胺 作用下， 以 苯 为溶剂， 反应 7.0h， 生成 azacyclooctano<2,1-b>-4(3H)-quinazolinone
  参考文献：
  名称：

  Novel ring enlargement of lactams via quinazolinone annelation. A facile route to benzoannelated large-membered cyclic 1,5-diamines

  摘要：

  A novel route to benzoannelated large-membered cyclic 1,5-diamines from lactams is described. Thus, n-membered lactams 1 were N-acylated by o-azidobenzoyl chloride 5 to afford the corresponding imides 4. These were treated with tributylphosphine and underwent an intramolecular aza-Wittig reaction to give n-membered ring-fused quinazolinones 2 in 84-96% yield. By reductive cleavage of 2 with BH3.THF, (n+4)-membered cyclic diamines 3 were obtained in 52-95% yield.

  DOI：

  10.1021/jo00004a036

文献信息

• Nitrogen bridgehead compounds. 66. Bronchodilator nitrogen bridgehead compounds with a pyrimidinone moiety
  作者：Istvan Hermecz、Lelle Vasvari-Debreczy、Agnes Horvath、Maria Balogh、Jozsef Kokosi、Christine DeVos、Ludovic Rodriguez

  DOI：10.1021/jm00392a003

  日期：1987.9

  New types of bronchodilator agents, bi- and tricyclic nitrogen bridgehead compounds with a pyrimidin-4(3H)-one ring, were synthesized and evaluated for bronchodilator activity against serotonin-, histamine-, and acetylcholine-induced spasms in the guinea pig Konzett-Rössler test. The structure-activity relationships are discussed. The effects of some bi- and tricyclic derivatives on the human bronchus

  合成了新型的支气管扩张剂，即具有嘧啶4（3H）-环的双环和三环氮桥头化合物，并评估了其对豚鼠Konzett-中血清素，组胺和乙酰胆碱诱导的痉挛的支气管扩张活性。 Rössler测试。讨论了构效关系。还研究了一些双环和三环衍生物对人支气管的影响。在分离的豚鼠回肠和气管上测试了同源的三环化合物68和69，并在毛果芸香碱处理的狗中研究了化合物69的作用。选择Azepino [2,1-b]喹唑啉（69; CHINOIN-1289）进行进一步的生化和临床研究。
• One-Pot Synthesis of Simple Alkaloids: 2,3-Polymethylene-4(3&lt;i&gt;H&lt;/i&gt;)-quinazolinones, Luotonin A, Tryptanthrin, and Rutaecarpine
  作者：Katherine Chae Jahng、Seung Ill Kim、Dong Hyeon Kim、Chang Seob Seo、Jong-Keun Son、Seung Ho Lee、Eung Seok Lee、Yurngdong Jahng

  DOI：10.1248/cpb.56.607

  日期：——

  One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl2 is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

  本文描述了从邻氨基苯甲酸、相应的内酰胺和SOCl2中一锅合成多种2,3-聚甲基-4(3H)-喹唑啉酮的方法，该方法可用于合成简单的4(3H)-喹唑啉酮衍生物生物碱，如鲁托霉素A、曲普坦和鲁托卡品。
• Novel tricyclic quinazolinimines and related tetracyclic nitrogen bridgehead compounds as cholinesterase inhibitors with selectivity towards butyrylcholinesterase
  作者：Michael Decker、Fabian Krauth、Jochen Lehmann

  DOI：10.1016/j.bmc.2005.10.044

  日期：2006.3

  Tetracyclic nitrogen bridgehead compounds, dibenzodiazecines and tricyclic quinazolinimines, in which the size of the alicyclic ring system and the length of the alkyl chain between the quinazolinimine moiety and a phenyl ring connected to the imine nitrogen atom were changed systematically, were synthesized and their ability to inhibit acetyl- and butyrylcholinesterase (AChE/BChE), respectively, was

  合成了四环氮桥头化合物，二苯并二氮杂胺和三环喹唑啉亚胺，其中脂环环系统的大小以及喹唑啉亚胺部分和与亚胺氮原子相连的苯环之间的烷基链的长度被系统地改变，并且它们具有分别评估了乙酰胆碱酯酶和丁酰胆碱酯酶（AChE / BChE）的抑制作用。与加兰他敏和卡巴拉汀相比，已鉴定出中度和强效BChE抑制剂，它们对混合BChE表现出混合的亲和力或中度或高度选择性。
• Transition-metal complex-catalyzed reductive N-heterocyclization: synthesis of 4(3H)-quinazolinone derivatives from N-(2-nitrobenzoyl)amides
  作者：Motohiro Akazome、Teruyuki Kondo、Yoshihisa Watanabe

  DOI：10.1021/jo00054a008

  日期：1993.1

  Several ruthenium and platinum complexes smoothly catalyze the reductive N-heterocyclization of N-(2-nitrobenzoyl)amides under carbon monoxide pressure to afford the corresponding 4(3H)-quinazolinone derivatives, including some quinazolinone alkaloids, in good yields.
• Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide
  作者：Yutaka Nishiyama、Masaharu Hirose、Wataru Kitagaito、Noboru Sonoda

  DOI：10.1016/s0040-4039(02)00035-7

  日期：2002.3

  A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.