3-氮杂双环[3.2.1]辛烷-2-酮 | 16994-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 3-氮杂双环[3.2.1]辛烷-2-酮
• 英文名称: 3-aza-2-oxobicyclo<3.2.1>octane
• 英文别名: 3-azabicyclo[3.2.1]octan-2-one；3-aza-bicyclo[3.2.1]octan-2-one；3-Aza-bicyclo<3.2.1>octanon-(2)；3-Azabicyclo<3.2.1>octane-2-one；3-Azabicyclo<3.2.1>octanon-(2)；3-Azabicyclo<3.2.1>octan-2-on
• CAS: 16994-00-6
• 化学式: C₇H₁₁NO
• mdl: MFCD11502568
• 分子量: 125.17
• InChiKey: VIJCSXWSAGILRP-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174.5 °C
• 沸点：
  297.4±9.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  3-氮杂双环[3.2.1]辛烷-2-酮 在 potassium permanganate 作用下， 生成 (1S,3R)-环戊烷-1,3-二甲酸
  参考文献：
  名称：

  Schmidt and Beckmann Reactions of Norcamphor and Cyclopentanonorcamphor¹

  摘要：

  DOI：

  10.1021/jo01065a004
• 作为产物：
  描述：

  3-((R)-1-Phenyl-ethyl)-3-aza-bicyclo[3.2.1]octan-2-one 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以70%的产率得到3-氮杂双环[3.2.1]辛烷-2-酮
  参考文献：
  名称：

  Syntheses and rearrangements of spirocyclic oxaziridines derived from unsymmetrical ketones

  摘要：

  Oxaziridines provide useful alternatives to the Beckmann rearrangement and Schmidt reaction for ring enlargement of cyclic ketones. The procedure involves the condensation of the ketone in question with optically active alpha-methylbenzylamine, oxidation of the resultant imine, and photolysis to afford ring-expanded lactams. The alpha-phenylethyl substituent can be removed after photolysis to yield the N-unsubstituted lactam. When a distal ketone substituent is present, the oxaziridines can be synthesized stereoselectively. Thus, optically active ketones can be converted to either ring-expanded lactam by choice of either enantiomer of optically active alpha-methylbenzylamine. Ketones bearing adjacent substitution are generally not amenable to such regiocontrol because the resident substituent is the key stereocontrol element for the oxaziridine synthesis, although a notable exception is 2-methoxycyclohexanone. Stereogenic centers present in such compounds undergo epimerization during the couse of the reaction sequence; in addition, substrates containing substantial amounts of enamine give rise to novel doubly oxygenated products upon oxidation. Finally, the conformational behavior of the side chains in both oxaziridines and their product lactams permits some key stereochemical assignments to be made, on the basis of chemical shift trends in the NMR spectra of these materials.

  DOI：

  10.1021/jo00002a006

文献信息

• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：——

  公开号：US20020045747A1

  公开（公告）日：2002-04-18

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  公开了抑制β-淀粉样肽释放和/或其合成的化合物，因此可用于治疗阿尔茨海默病。还公开了包含抑制β-淀粉样肽释放和/或其合成的化合物的药物组合物，以及使用这些药物组合物预防性和治疗性治疗阿尔茨海默病的方法。
• [EN] CENTRALLY ACTIVE AND ORALLY BIOAVAILABLE ANTIDOTES FOR ORGANOPHOSPHATE EXPOSURE AND METHODS FOR MAKING AND USING THEM<br/>[FR] ANTIDOTES CENTRALEMENT ACTIFS ET BIO-DISPONIBLES PAR VOIE ORALE UTILISABLES EN CAS D'EXPOSITION AUX ORGANOPHOSPHATES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV CALIFORNIA

  公开号：WO2014127315A1

  公开（公告）日：2014-08-21

  In alternative embodiments, the invention provides nucleophilic hydroxyimino- acetamido alkylamine antidotes that cross the blood-brain barrier (BBB) to catalyze the hydrolysis of organophosphate (OP)-inhibited human acetylcholinesterase (hAChE) in the central nerve system (CNS). The hydroxyimino-acetamido alkylamines of the invention are designed to fit within AChE active center gorge dimensions, bind with reasonable affinity, and react with the conjugated phosphate atom in the gorge. The hydroxyimino- acetamido alkylamines of the invention are also designed to possess ionization states that govern affinity and reactivity for the two linked hAChE re-activation steps. In alternative embodiments, the invention provides pumps, devices, subcutaneous infusion devices, continuous subcutaneous infusion devices, infusion pens, needles, reservoirs, ampoules, a vial, a syringe, a cartridge, a disposable pen or jet injector, a prefilled pen or a syringe or a cartridge, a cartridge or a disposable pen or jet injector, a two chambered or multi- chambered pump, a syringe, a cartridge or a pen or a jet injector, comprising a compound of the invention.

  在另一种实施方式中，该发明提供了能够穿过血脑屏障（BBB）的亲核羟亚胺-乙酰胺基烷胺解毒剂，用于催化有机磷（OP）抑制的人类乙酰胆碱酯酶（hAChE）在中枢神经系统（CNS）中的水解。该发明的羟亚胺-乙酰胺基烷胺设计成适合AChE活性中心峡谷尺寸，具有合理的亲和力，并与峡谷中的共轭磷原子发生反应。该发明的羟亚胺-乙酰胺基烷胺还设计成具有调控两个连接的hAChE重新激活步骤的亲和力和反应性的电离态。在另一种实施方式中，该发明提供了泵、装置、皮下输注装置、连续皮下输注装置、输注笔、针头、储液器、安瓿、小瓶、注射器、笔式注射器或喷射器、预装笔或注射器或装置、装置或一次性笔或喷射器、两室或多室泵、注射器、装置或笔或喷射器，其中包括该发明的化合物。
• Beckmann rearrangements in the bicyclo[2.2.1]heptan-2-one series
  作者：Peter A. Hunt、Christopher J. Moody

  DOI：10.1016/s0040-4039(01)93944-9

  日期：1989.1

  In contrast to norcamphor oxime (2), the E-oxime (6), derived from the acetonide of 5,6-dihydroxybicyclo[2.2.1]heptan-2-one, undergoes regiospecific Beckmann rearrangement to give the lactam (7).

  与正樟脑肟（2）相反，衍生自5，6-二羟基双环[2.2.1]庚-2-的丙酮化物的E-肟（6）经过区域特异性贝克曼重排而得到内酰胺（7）。
• [EN] PIPERIDIN-1- YL-N-PYRYDI NE-3-YL-2-OXOACET AM IDE DERIVATIVES USEFUL FOR THE TREATMENT OF MTAP-DEFICIENT AND/OR MT A-ACCUMULATING CANCERS<br/>[FR] DÉRIVÉS DE PIPÉRIDIN-1-YL-N-PYRYDINE-3-YL-2-OXO-ACÉTAMIDE UTILES POUR LE TRAITEMENT DE CANCERS DÉFICIENTS EN MTAP ET/OU ACCUMULANT MTA
  申请人：TANGO THERAPEUTICS INC

  公开号：WO2022026892A1

  公开（公告）日：2022-02-03

  Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R6, R7, R8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式（I）提供化合物及其药用盐，以及药物组合物；其中R1、R2、R3、R4、R6、R7、R8和n的定义如本文所述。本发明的化合物被认为对预防和治疗各种疾病条件有用。
• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting B-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：——

  公开号：US20020173504A1

  公开（公告）日：2002-11-21

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  本发明涉及抑制&bgr;-淀粉样肽的释放和/或合成的化合物，因此具有治疗阿尔茨海默病的效用。还公开了包含抑制&bgr;-淀粉样肽释放和/或合成的化合物的药物组合物，以及使用这种药物组合物预防和治疗阿尔茨海默病的方法。