rac-7,7-ethylenodioxy-3-trifluoromethanesulfonyloxybicyclo[3.3.1]non-2-ene | 206259-87-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: rac-7,7-ethylenodioxy-3-trifluoromethanesulfonyloxybicyclo[3.3.1]non-2-ene
• 英文别名: Spiro[1,3-dioxolane-2,7'-bicyclo[3.3.1]non-2-ene]-3'-yl trifluoromethanesulfonate
• CAS: 206259-87-2
• 化学式: C₁₂H₁₅F₃O₅S
• 分子量: 328.309
• InChiKey: DSQADQIDRCBZJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  rac-7,7-ethylenodioxy-3-trifluoromethanesulfonyloxybicyclo[3.3.1]non-2-ene 在 盐酸 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 7-ethylbicyclo[3.3.1]non-6-en-3-one
  参考文献：
  名称：

  Enantioselective synthesis of tacrine–huperzine A hybrids. Preparative chiral MPLC separation of their racemic mixtures and absolute configuration assignments by X-ray diffraction analysis

  摘要：

  A new synthesis of racemic 7-substituted bicyclo[3.3.1]non-6-en-3-ones, rac-4, whose key-step involves the reaction of a vinyl triflate, rac-7, with an organometallic reagent, has been developed. This procedure has been applied to the enantioselective synthesis of (+)- and (-)-7-ethylbicyclo[3.3.1]non-6-en-3-one, (+)- and (-)-4b, from which both enantiomers of the cholinesterase inhibitor, tacrine-huperzine A hybrid, 9b, have been obtained. Rac-9b and its related compounds rac-9a and rac-10a were separated into their enantiomers on a preparative scale by medium pressure liquid chromatography (MPLC) using microcrystalline cellulose triacetate as the chiral stationary phase. X-ray diffraction analysis of (-)-10a as the o-iodobenzoic acid salt, allowed us to establish its absolute configuration and deduce those of other enantiopure tacrine-huperzine A hybrids. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00029-9
• 作为产物：
  描述：

  三氟甲烷磺基苯胺 、 spiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-7-one 在 lithium diisopropyl amide 作用下， 生成 rac-7,7-ethylenodioxy-3-trifluoromethanesulfonyloxybicyclo[3.3.1]non-2-ene
  参考文献：
  名称：

  Enantioselective synthesis of tacrine–huperzine A hybrids. Preparative chiral MPLC separation of their racemic mixtures and absolute configuration assignments by X-ray diffraction analysis

  摘要：

  A new synthesis of racemic 7-substituted bicyclo[3.3.1]non-6-en-3-ones, rac-4, whose key-step involves the reaction of a vinyl triflate, rac-7, with an organometallic reagent, has been developed. This procedure has been applied to the enantioselective synthesis of (+)- and (-)-7-ethylbicyclo[3.3.1]non-6-en-3-one, (+)- and (-)-4b, from which both enantiomers of the cholinesterase inhibitor, tacrine-huperzine A hybrid, 9b, have been obtained. Rac-9b and its related compounds rac-9a and rac-10a were separated into their enantiomers on a preparative scale by medium pressure liquid chromatography (MPLC) using microcrystalline cellulose triacetate as the chiral stationary phase. X-ray diffraction analysis of (-)-10a as the o-iodobenzoic acid salt, allowed us to establish its absolute configuration and deduce those of other enantiopure tacrine-huperzine A hybrids. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00029-9

文献信息

• 7-AZAINDOLE DERIVATIVES AND THEIR USE IN THE INHIBITION OF C-JUN N-TERMINAL KINASE
  申请人：GRACZYK Piotr Pawel

  公开号：US20100069354A1

  公开（公告）日：2010-03-18

  The present invention provides a compound of formula (I); or a pharmaceutically acceptable salt thereof, the use of a compound of formula (I) or a pharmaceutically acceptable salt thereof in the inhibition of c-Jun N-terminal kinase (JNK) activity and the use in medicine and particularly in the treatment of neurodegenerative disorders, inflammatory diseases and/or and autoimmune diseases. The invention also provides processes for the manufacture of said compounds of formula (I) or a pharmaceutically acceptable salt thereof and compositions containing them.

  本发明提供了公式（I）的化合物；或其药学上可接受的盐，使用公式（I）的化合物或其药学上可接受的盐来抑制c-Jun N末端激酶（JNK）活性，并用于医药学，特别是用于治疗神经退行性疾病、炎症性疾病和/或自身免疫性疾病。本发明还提供了制备所述公式（I）的化合物或其药学上可接受的盐的方法和含有它们的组合物。
• NOVEL POLYCYCLIC AMINOPYRIDINE COMPOUNDS AS ACETYLCHOLINESTERASE INHIBITORS, PREPARATION PROCESS AND USE THEREOF
  申请人：Medichem, S.A.

  公开号：EP0796849B1

  公开（公告）日：2003-11-19
• US5965569A
  申请人：——

  公开号：US5965569A

  公开（公告）日：1999-10-12
• US8178552B2
  申请人：——

  公开号：US8178552B2

  公开（公告）日：2012-05-15
• [EN] 7-AZAINDOLE DERIVATIVES AND THEIR USE IN THE INHIBITION OF C-JUN N-TERMINAL KINASE<br/>[FR] DÉRIVÉS DE 7-AZAINDOLE ET LEUR UTILISATION DANS L'INHIBITION DE C-JUN N-TERMINAL KINASE
  申请人：EISAI LONDON RES LAB LTD

  公开号：WO2008095944A1

  公开（公告）日：2008-08-14

  [EN] The present invention provides a compound of formula (I); or a pharmaceutically acceptable salt thereof, the use of a compound of formula (I) or a pharmaceutically acceptable salt thereof in the inhibition of c-Jun N-terminal kinase (JNK) activity and the use in medicine and particularly in the treatment of neurodegenerative disorders, inflammatory diseases and/or and autoimmune diseases. The invention also provides processes for the manufacture of said compounds of formula (I) or a pharmaceutically acceptable salt thereof and compositions containing them.
  [FR] La présente invention porte sur un composé de formule (I) ou un sel pharmaceutiquement acceptable de celui-ci ; sur l'utilisation de composé de formule (I) ou d'un sel pharmaceutiquement acceptable de celui-ci dans l'inhibition de l'activité C-Jun N-terminal kinase (JNK) ; et sur l'utilisation en médecine et, en particulier, dans le traitement de troubles neurodégénératifs, de maladies inflammatoires et/ou de maladies auto-immunes. L'invention porte également sur des procédés de fabrication desdits composés de formule (I) ou sur un sel pharmaceutiquement acceptable de ceux-ci, et sur des compositions les contenant.