tert-butyl 5-oxo-6-(p-tolylsulfonyl)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate | 227454-54-8

• 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: tert-butyl 5-oxo-6-(p-tolylsulfonyl)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate
• 英文别名: 5-Oxo-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester；Tert-butyl 5-(4-methylphenyl)sulfonyl-6-oxo-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate
• CAS: 227454-54-8
• 化学式: C₁₈H₂₁NO₅S
• 分子量: 363.434
• InChiKey: HSHUICMDSLHIBV-UHFFFAOYSA-N

物化性质

• 沸点：
  546.9±50.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-oxo-6-(p-tolylsulfonyl)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以85%的产率得到tert-butyl (1SR,4RS,5SR,6RS)-5-hydroxy-6-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 1,2-Diamine Derivatives of 7-Azabicyclo[2.2.1]heptane. New Leads as Glycosidase Inhibitors and Rigid Scaffolds for the Preparation of Peptide Analogues

  摘要：

  Enantiomerically pure alcohols (-)- and (+)-7-tert-butoxycarbonyl-6-endo-p-toluenesulfonyl-7azabicyclo[2.2.1]hept-2-en-5-endo-ol ((-)-11 and (+)-11) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrroel and 2-bromo-1-p-toluenesulfonylacetylene, including a resolution method. These two alcohols were converted into (+)- and (-)-5-exo-amino-7-(tertbutoxycarbonyl))-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane ((+)-18 and (-)-18) and (+)and (-)-5-endo-amino-7-(tert-butoxycarbonyl)-2,3-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane ((+)-19 and (-)-19) after adequate fanctionalization and desulfonylation steps. The corresponding conformationally constrained bicyclic 1,2-diamines (+)-4, (-)-4, (+/-)-5, (+/-)-6, (+)-7, and (-)-7 were obtained from the protected precursors 18 and 19 and evaluated as glycosidase inhibitors. Diamines (+)-4, (-)-4, (+)-6, and (-)-6 can be seen as new nonpeptide molecular scaffolds for the design of peptide analogues.

  DOI：

  10.1021/jo0301088
• 作为产物：
  描述：

  1-吡咯甲酸叔丁酯 在 盐酸 、 水 、 二乙胺 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 tert-butyl 5-oxo-6-(p-tolylsulfonyl)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate
  参考文献：
  名称：

  2-Bromoethynyl aryl sulfones as versatile dienophiles: a formal synthesis of epibatidine

  摘要：

  我们开发了一种 2-溴乙炔基芳基砜的简便合成方法；介绍了这些多用途亲二烯化合物在 [4+2] 环加成反应中的反应活性以及在表巴丁正式合成中的应用。

  DOI：

  10.1039/a900970a

文献信息

• Synthesis of 5-endo-, 5-exo-, 6-endo- and 6-exo-hydroxylated analogues of epibatidine
  作者：Zhi-Liang Wei、Clifford George、Alan P. Kozikowski

  DOI：10.1016/s0040-4039(03)00737-8

  日期：2003.5

  A convenient, high-yield synthesis of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (7) was developed by SmI2-mediated desulfonylation of 6. Thus, 5-endo-, 5-exo-, 6-endo-, and 6-exo-hydroxylated epibatidine analogues 2a,b and 3a,b were synthesized from 7 by using a Pd(PPh3)4-catalyzed reductive Heck coupling reaction and SmI2-mediated reduction of the carbonyl group as the key steps. Other reaction conditions

  N -Boc-7-氮杂双环[2.2.1] hept-5-en-2-one（7）的一种便捷，高产率的合成方法是通过SmI 2介导的6的脱磺酰作用开发的。因此，通过使用Pd（PPh 3）4催化的还原性Heck偶联从7合成了5-内-，5-外-，6-内-和6-外-羟基化的依巴替丁类似物2a，b和3a，b。反应和SmI 2-介导的羰基还原是关键步骤。还研究了还原性Heck方法和还原步骤的其他反应条件。
• Ligands for Nicotinic Acetylcholine Receptors, and Methods of Making and Using Them
  申请人：Kozikowski Alan P.

  公开号：US20080132486A1

  公开（公告）日：2008-06-05

  One aspect of the present invention relates to heterocyclic compounds that are ligands for nicotinic acetylcholine receptors. A second aspect of the invention relates to the use of a compound of the invention for modulation of a mammalian nicotinic acetylcholine receptor. The present invention also relates to the use of a compound of the invention for treating a mammal suffering from Alzheimer's disease, Parkinson's disease, dyskinesias, Tourette's syndrome, schizophrenia, attention deficit disorder, anxiety, pain, depression, obsessive compulsive disorder, chemical substance abuse, alcoholism, memory deficit, pseudodementia, Ganser's syndrome, migraine pain, bulimia, obesity, premenstrual syndrome or late luteal phase syndrome, tobacco abuse, post-traumatic syndrome, social phobia, chronic fatigue syndrome, premature ejaculation, erectile difficulty, anorexia nervosa, disorders of sleep, autism, mutism or trichtillomania.

  本发明的一个方面涉及杂环化合物，其是乙酰胆碱受体的配体。本发明的第二个方面涉及使用本发明的化合物来调节哺乳动物的乙酰胆碱受体。本发明还涉及使用本发明的化合物来治疗患有阿尔茨海默病、帕金森病、运动障碍、抽动症、精神分裂症、注意力缺陷障碍、焦虑、疼痛、抑郁症、强迫症、化学物质滥用、酗酒、记忆力障碍、假性痴呆、甘瑟综合征、偏头痛疼痛、贪食症、肥胖症、月经前综合征或黄体酮期后综合征、烟草滥用、创伤后应激障碍、社交恐惧症、慢性疲劳综合征、早泄、勃起障碍、厌食症、睡眠障碍、自闭症、哑症或拔毛癖的哺乳动物。
• BETA-HYDROXY HETEROCYCLIC AMINES AND THEIR USE IN THE TREATMENT OF HYPERGLYCAEMIA
  申请人：ATROGI AB

  公开号：US20200277259A1

  公开（公告）日：2020-09-03

  There is herein provided a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein X, R 1 , ring A, m and n have meanings as provided in the description.
• US8030300B2
  申请人：——

  公开号：US8030300B2

  公开（公告）日：2011-10-04
• [EN] LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, AND METHODS OF MAKING AND USING THEM<br/>[FR] LIGANDS POUR LES RECEPTEURS DE L'ACETYLCHOLINE NICOTINIQUE, ET PROCEDES DE PRODUCTION ET D'UTILISATION DE CES LIGANDS
  申请人：UNIV GEORGETOWN

  公开号：WO2005000806A2

  公开（公告）日：2005-01-06

  One aspect of the present invention relates to heterocyclic compounds that are ligands for nicotinic acetylcholine receptors. A second aspect of the invention relates to the use of a compound of the invention for modulation of a mammalian nicotinic acetylcholine receptor. The present invention also relates to the use of a compound of the invention for treating a mammal suffering from Alzheimer's disease, Parkinson's disease, dyskinesias, Tourette's syndrome, schizophrenia, attention deficit disorder, anxiety, pain, depression, obsessive compulsive disorder, chemical substance abuse, alcoholism, memory deficit, pseudodementia, Ganser's syndrome, migraine pain, bulimia, obesity, premenstrual syndrome or late luteal phase syndrome, tobacco abuse, post-traumatic syndrome, social phobia, chronic fatigue syndrome, premature ejaculation, erectile difficulty, anorexia nervosa, disorders of sleep, autism, mutism or trichtillomania.