9-Acetyl-9-azabicyclo<3.3.1>nonan-3-on | 36146-88-0

• 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: 9-Acetyl-9-azabicyclo<3.3.1>nonan-3-on
• 英文别名: 9-Acetyl-norgranatanon-(3)；N-Acetyl-nor-pseudopelletierin；9-acetyl-9-aza-bicyclo[3.3.1]nonan-3-one；9-Acetyl-9-aza-bicyclo[3.3.1]nonan-3-on；9-Acetyl-9-azabicyclo[3.3.1]nonan-3-one；9-acetyl-9-azabicyclo[3.3.1]nonan-3-one
• CAS: 36146-88-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: LQVTXXUZTMGSJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  9-氮杂双环[3.3.1]壬烷-3-酮	9-azabicyclo[3.3.1]nonan-3-one	4390-39-0	C8H13NO	139.197

反应信息

• 作为反应物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 9-Acetyl-9-azabicyclo<3.3.1>nonan-3-on 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives

  摘要：

  The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine with an exo-tropanyl unit led to the identification of compound 15 which provides a combination of excellent potency against human and murine receptors, drug-like properties and pharmacokinetics, thus providing a valuable tool for the evaluation of CXCR3 antagonists in models of human disease. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.109
• 作为产物：
  描述：

  9-氮杂双环[3.3.1]壬烷-3-酮 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到9-Acetyl-9-azabicyclo<3.3.1>nonan-3-on
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives

  摘要：

  The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine with an exo-tropanyl unit led to the identification of compound 15 which provides a combination of excellent potency against human and murine receptors, drug-like properties and pharmacokinetics, thus providing a valuable tool for the evaluation of CXCR3 antagonists in models of human disease. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.109

文献信息

• Beiträge zur Tropanchemie, 1. Mitt. 3β-Substituierte Tropan-Derivate
  作者：W. Schneider、B. Lang、F. Schumann

  DOI：10.1002/ardp.19753080509

  日期：——

  Es wird über Synthesen von 3β‐substituierten Tropan‐Derivaten berichtet, die zum Aufbau der Nortropan‐3β‐essigsäure (1a) und deren Folgeprodukte geeignet sind. Während die isomere‐3α‐Verbindung 2a leicht zugänglich ist, lassen sich Nortropan‐3β‐Derivate wie 5h am besten über N‐Benzyl‐nortropane herstellen. In der 3β‐Tropan‐Reihe scheitert die Kettenverlängerung des β‐ständigen Substituenten an der

  报道了适用于合成去甲托烷 3β-乙酸 (1a) 及其衍生物的 3β-取代的托烷衍生物的合成。虽然异构体 3α 化合物 2a 很容易获得，但最好通过 N-苄基-去甲托烷制备去甲托烷 3β 衍生物，例如 5h。在 3β-托烷系列中，由于环铵盐 7 的形成，β-取代基的扩链失败。所示托烷的构型由 1H NMR 光谱证实。
• Alder et al., Justus Liebigs Annalen der Chemie, 1959, vol. 620, p. 73,87
  作者：Alder et al.

  DOI：——

  日期：——
• Polonovski; Polonovski, Bulletin de la Societe Chimique de France, 1927, vol. <4>41, p. 1206
  作者：Polonovski、Polonovski

  DOI：——

  日期：——
• Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives
  作者：Robert J. Watson、Daniel R. Allen、Helen L. Birch、Gayle A. Chapman、Frances C. Galvin、Louise A. Jopling、Roland L. Knight、Dorica Meier、Kathryn Oliver、Johannes W.G. Meissner、David A. Owen、Elizabeth J. Thomas、Neil Tremayne、Sophie C. Williams

  DOI：10.1016/j.bmcl.2007.10.109

  日期：2008.1

  The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine with an exo-tropanyl unit led to the identification of compound 15 which provides a combination of excellent potency against human and murine receptors, drug-like properties and pharmacokinetics, thus providing a valuable tool for the evaluation of CXCR3 antagonists in models of human disease. (C) 2007 Elsevier Ltd. All rights reserved.