bicyclo<3.3.1>nonan-3-one | 10036-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bicyclo<3.3.1>nonan-3-one
• 英文别名: Bicyclo<3.3.1>-3-on；bicyclo[3.3.1]nonan-3-one；(1S,5R)-bicyclo[3.3.1]nonan-3-one
• CAS: 10036-09-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: ANFLIDKLELMAAQ-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  bicyclo<3.3.1>nonan-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 endo-Bicyclo[3.3.1]nonan-3-ol
  参考文献：
  名称：

  Bicyclo[3.3.1]nonanes as synthetic intermediates. IV. Behavior of bicyclo[3.n.1]alkan-3-ones toward the Baeyer-Villiger oxidation.

  摘要：

  描述了双环[3.n.1]烷-3-酮和相关系统的拜耳-维利格氧化。双环[3.3.1]壬烷-2-酮（8）被氧化成相应的内酯，发现通过后续的甲醇解转化为顺式-1,3-二取代环己烷系统。同时，3-氧代系统（2）表现出异常的抗氧化性。假设C-7处的轴向（内）质子引起的“背面空间位阻”是不活跃的根源。在双环系统（2、3、4）的拜耳-维利格反应中，酮

  DOI：

  10.1248/cpb.27.222
• 作为产物：
  描述：

  endo-Bicyclo[3.3.1]nonan-3-ol 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 作用下， 生成 bicyclo<3.3.1>nonan-3-one
  参考文献：
  名称：

  Conformational analysis and chromic acid oxidation. The rationalization of the rates of oxidation of secondary alcohols

  摘要：

  DOI：

  10.1021/ja00442a016

文献信息

• [EN] SUBSTITUTED-QUINOXALINE-TYPE BRIDGED-PIPERIDINE COMPOUNDS AND THE USES THEREOF<br/>[FR] COMPOSÉS PIPÉRIDINE À LIAISON ET SUBSTITUÉS PAR UNE QUINOXALINE, ET LEURS UTILISATIONS
  申请人：PURDUE PHARMA LP

  公开号：WO2010010458A1

  公开（公告）日：2010-01-28

  The invention relates to Substituted-Quinoxaline-Type Bridged-Piperidine Compounds, compositions comprising an effective amount of a Substituted-Quinoxaline- Type Bridged-Piperidine Compound and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Substituted-Quinoxaline-Type Bridged-Piperidine Compound.

  这项发明涉及取代喹喔啉型桥式哌啶化合物，包括有效量的取代喹喔啉型桥式哌啶化合物的组合物，以及治疗或预防疼痛等疾病的方法，包括向需要治疗的动物施用有效量的取代喹喔啉型桥式哌啶化合物。
• Momose, Takefumi; Muraoka, Osamu; Masuda, Kikuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 9, p. 3730 - 3733
  作者：Momose, Takefumi、Muraoka, Osamu、Masuda, Kikuo

  DOI：——

  日期：——
• Momose,T.; Muraoka,O., Chemical and pharmaceutical bulletin, 1978, vol. 26, p. 2589 - 2593
  作者：Momose,T.、Muraoka,O.

  DOI：——

  日期：——
• Asymmetric functionalization of conformationally distinctive Cs-symmetric cis-[n.3.1] bicyclic ketones. Definition of the absolute course of enantio- and diastereodifferentiation
  作者：Theodore L. Underiner、Leo A. Paquette

  DOI：10.1021/jo00046a028

  日期：1992.9

  The four C(s)-symmetric cis[n.3.1] bicyclic ketones where n = 3, 5, 7, and 9 were acetalized with (R,R)-2,4-pentanediol, and the resulting derivatives were cleaved with triisobutylaluminum (TRIBAL). The first three examples, all of which have their polymethylene chain rigidly fixed in a diaxial orientation, undergo ring opening with very high diastereoselectivity to give 5. In the fourth case (n = 9), the chain is sufficiently long to be attached in a diequatorial manner. The response of 4d to TRIBAL is to deliver a 1:1 mixture of 11 and 12. The stereochemical course of epoxidation and cyclopropanation reactions of these enol ethers has been assessed. Where 5 and 11 are concerned, these functionalization reactions are 100% pi-facially selective. Only 12 is the exception. Also examined in this study was the enantioselective deprotonation of the same ketones with the enantiomerically pure lithium amide base 27. The resulting enolates were trapped as their silyl enol ethers and transformed directly into optically active alpha-hydroxy ketones and alpha,beta-unsaturated enones by epoxidation and selenenylation-oxidative elimination, respectively. The sense of the observed enantioselectivity was the same irrespective of the diaxial or diequatorial disposition of the (CH2)n loop. However, the asymmetry induced by this means was consistently opposite to that realized by TRIBAL-promoted acetal cleavage. When these complementary processes are compared at the alpha-hydroxy ketone stage, the acetal cleavage-epoxidation option was invariably 100% enantioselective; greater variability in optical purity was seen via the deprotonation-silylation-epoxidation option. The possible mechanistic basis of these observations is explored.
• Conformational analysis and chromic acid oxidation. The rationalization of the rates of oxidation of secondary alcohols
  作者：Paul Mueller、Jean C. Perlberger

  DOI：10.1021/ja00442a016

  日期：1976.12