benzyl 4-oxooctahydroquinoline-1(2H)-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-oxooctahydroquinoline-1(2H)-carboxylate
• 英文别名: benzyl (cis)-4-oxooctahydroquinoline-1(2H)-carboxylate；benzyl (4aS,8aR)-4-oxo-2,3,4a,5,6,7,8,8a-octahydroquinoline-1-carboxylate
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: PEVUYLZPVIJLMP-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 4-oxooctahydroquinoline-1(2H)-carboxylate 在 N-羟基-7-氮杂苯并三氮唑 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(4R,4aS,8aR)-4-hydroxy-4-phenyl-2,3,4a,5,6,7,8,8a-octahydroquinolin-1-yl]-(1H-1,2,4-triazol-5-yl)methanone
  参考文献：
  名称：

  Decahydroquinoline amides as highly selective CB2 agonists: Role of selectivity on in vivo efficacy in a rodent model of analgesia

  摘要：

  A novel series of decahydroquinoline CB2 agonists is described. Optimization of the amide substituent led to improvements in CB2/CB1 selectivity as well as physical properties. Two key compounds were examined in the rat CFA model of acute inflammatory pain. A moderately selective CB2 agonist was active in this model. A CB2 agonist lacking functional CB1 activity was inactive in this model despite high in vivo exposure both peripherally and centrally. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.078
• 作为产物：
  描述：

  八氢对苯二酚-4(1H)-酮 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 benzyl 4-oxooctahydroquinoline-1(2H)-carboxylate
  参考文献：
  名称：

  Decahydroquinoline amides as highly selective CB2 agonists: Role of selectivity on in vivo efficacy in a rodent model of analgesia

  摘要：

  A novel series of decahydroquinoline CB2 agonists is described. Optimization of the amide substituent led to improvements in CB2/CB1 selectivity as well as physical properties. Two key compounds were examined in the rat CFA model of acute inflammatory pain. A moderately selective CB2 agonist was active in this model. A CB2 agonist lacking functional CB1 activity was inactive in this model despite high in vivo exposure both peripherally and centrally. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.078

文献信息

• Formal Alkyne Aza-Prins Cyclization: Gold(I)-Catalyzed Cycloisomerization of Mixed N,O-Acetals Generated from Homopropargylic Amines to Highly Substituted Piperidines
  作者：Cheoljae Kim、Hyo Jin Bae、Ji Hyung Lee、Wook Jeong、Haejin Kim、Vasu Sampath、Young Ho Rhee

  DOI：10.1021/ja906744r

  日期：2009.10.21

  cycloisomerization to access highly substituted piperidines has been developed. By combining a conceptually new way of generating iminium ions using cationic gold(I) complexes and an efficient cyclization reaction that can minimize a potentially competing aza-Cope rearrangement, the proposed reaction successfully circumvents a long-standing problem in the classical aza-Prins reaction. Synthetic utility of the catalytic

  已经开发出一种新的金（I）催化的环异构化来获得高度取代的哌啶。通过将使用阳离子金 (I) 络合物生成亚胺离子的概念上新方法与可以最小化潜在竞争性 aza-Cope 重排的有效环化反应相结合，所提出的反应成功地规避了经典 aza-Prins 反应中长期存在的问题. 通过合成光学活性 2-烷基-哌啶-4-one 证明了催化反应的合成效用。
• DECAHYDROQUINOLINE ANALOGS AS CB2 RECEPTOR MODULATORS, USEFUL IN THE TREATMENT OF PAIN, RESPIRATORY AND NON-RESPIRATORY DISEASES
  申请人：Bilodeau Mark T.

  公开号：US20100099673A1

  公开（公告）日：2010-04-22

  The present invention relates to compounds represented by Formula (I): and pharmaceutically acceptable salts thereof. The present invention also provides pharmaceutical compositions comprising the instant compounds. This invention further provides methods to treat and prevent pain, respiratory and non-respiratory diseases.

  本发明涉及由式（I）表示的化合物及其药学上可接受的盐。本发明还提供了包含上述化合物的制药组合物。本发明还提供了治疗和预防疼痛、呼吸和非呼吸性疾病的方法。
• WO2008/88744
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] DECAHYDROQUINOLINE ANALOGS AS CB2 RECEPTOR MODULATORS<br/>[FR] ANALOGUES DE LA DÉCAHYDROQUINOLÉINE EN TANT QUE MODULATEURS DE RÉCEPTEUR CB2
  申请人：MERCK & CO INC

  公开号：WO2008088744A1

  公开（公告）日：2008-07-24

  [EN] The present invention relates to compounds represented by Formula (I): and pharmaceutically acceptable salts thereof. The present invention also provides pharmaceutical compositions comprising the instant compounds. This invention further provides methods to treat and prevent pain, respiratory and non-respiratory diseases.
  [FR] La présente invention porte sur des composés représentés par la Formule (I) : et sur les sels pharmaceutiquement acceptables de ceux-ci. La présente invention porte également sur des compositions pharmaceutiques comprenant les présents composés. Cette invention porte en outre sur des procédés pour traiter et prévenir la douleur, les maladies respiratoires et les maladies non respiratoires.
• Decahydroquinoline amides as highly selective CB2 agonists: Role of selectivity on in vivo efficacy in a rodent model of analgesia
  作者：Peter J. Manley、Amy Zartman、Daniel V. Paone、Christopher S. Burgey、Darrell A. Henze、Kimberly Della Penna、Reshma Desai、Michael D. Leitl、Wei Lemaire、Rebecca B. White、Suzie Yeh、Mark O. Urban、Stefanie A. Kane、George D. Hartman、Mark T. Bilodeau、B. Wesley Trotter

  DOI：10.1016/j.bmcl.2011.02.078

  日期：2011.4

  A novel series of decahydroquinoline CB2 agonists is described. Optimization of the amide substituent led to improvements in CB2/CB1 selectivity as well as physical properties. Two key compounds were examined in the rat CFA model of acute inflammatory pain. A moderately selective CB2 agonist was active in this model. A CB2 agonist lacking functional CB1 activity was inactive in this model despite high in vivo exposure both peripherally and centrally. (C) 2011 Elsevier Ltd. All rights reserved.