5-bromo-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene | 1345203-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-bromo-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene
• 英文别名: 3-bromo-11-(dichloromethylidene)tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene
• CAS: 1345203-43-1
• 化学式: C₁₂H₉BrCl₂
• 分子量: 304.013
• InChiKey: PLOBBIWKDISZAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromo-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 6.0h， 生成 N-{[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]methyl}cyclopropanamine
  参考文献：
  名称：

  [EN] N-CYCLOALKYL-N-[(FUSEDPHENYL)METHYLENE]-(THIO)CARBOXAMIDE DERIVATIVES
  [FR] DÉRIVÉS DE N-CYCLOALKYL-N-[(PHÉNYLE CONDENSÉ)MÉTHYLÈNE]-(THIO)CARBOXAMIDE

  摘要：

  本发明涉及杀真菌的N-环烷基-N-[(融合苯基)亚甲基]羧酰胺衍生物及其硫代羰基衍生物，其制备过程和制备中间体，其作为杀真菌剂的用途，尤其是以杀真菌组合物的形式和使用这些化合物或其组合物控制植物的植物病原真菌的方法。

  公开号：

  WO2014206954A1
• 作为产物：
  描述：

  9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-amine 在 氢溴酸 、 sodium nitrite 、 copper(I) bromide 作用下， 以 水 为溶剂， 反应 2.5h， 以30%的产率得到5-bromo-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene
  参考文献：
  名称：

  [EN] N-CYCLOALKYL-N-[(FUSEDPHENYL)METHYLENE]-(THIO)CARBOXAMIDE DERIVATIVES
  [FR] DÉRIVÉS DE N-CYCLOALKYL-N-[(PHÉNYLE CONDENSÉ)MÉTHYLÈNE]-(THIO)CARBOXAMIDE

  摘要：

  本发明涉及杀真菌的N-环烷基-N-[(融合苯基)亚甲基]羧酰胺衍生物及其硫代羰基衍生物，其制备过程和制备中间体，其作为杀真菌剂的用途，尤其是以杀真菌组合物的形式和使用这些化合物或其组合物控制植物的植物病原真菌的方法。

  公开号：

  WO2014206954A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES<br/>[FR] PROCÉDÉ D'ÉLABORATION D'AMIDES D'ACIDES CARBOXYLIQUES DE PYRAZOLES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011131546A1

  公开（公告）日：2011-10-27

  The invention relates to a process for the preparation of formula (I) which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species to (III), wherein X is chloro or bromo; reacting the halobenzyne with a fulvene (IV), to a compound of formula(V) wherein X is chloro or bromo; b) hydrogenating V in the presence of a suitable metal catalyst to a compound of formula (VI) wherein X is chloro or bromo; and either c1) reacting the compound of formula VI with NH3 in the presence of a catalyst comprising palladium and at least one ligand to the compound of formula (VII); and d) reacting the compound of formula VII in the presence of a base with a compound of formula (VIII), to the compound of formula I; or c2 reacting the compound of formula (VI) in the presence of a copper catalyst and a ligand with the compound of formula (VIIIa), to the compound of formula (I).

  本发明涉及一种制备式(I)的方法，该方法包括：a)将式(II)的化合物与有机金属物种反应，得到式(III)，其中X为氯或溴；将卤代苯与富烯(VI)反应，得到式(V)，其中X为氯或溴；b)在合适的金属催化剂存在下，氢化V得到式(VI)，其中X为氯或溴；并且c1)在钯和至少一种配体的催化剂存在下，将式VI的化合物与NH3反应，得到式(VII)的化合物；和d)在碱的存在下，将式(VII)的化合物与式(VIII)的化合物反应，得到式(I)的化合物；或者c2)在铜催化剂和配体的存在下，将式(VI)的化合物与式(VIIIa)的化合物反应，得到式(I)的化合物。
• [EN] PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'AMIDES D'ACIDE PYRAZOLECARBOXYLIQUE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011131545A1

  公开（公告）日：2011-10-27

  The invention relates to a process for the preparation of the compound of formula (I), which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species in an inert atmosphere to a halobenzyne of formula (X), reacting the halobenzyne of formula X so formed with cyclopentadiene to (III), b) reacting III in the presence of an inert solvent with an oxidant to (IV), c) reacing IV in the presence of a Lewis acid and a hydride source to (V), d) reacting V in the presence of an oxidizing agent, a base and an inert solvent to (VI), e) converting VI in the presence of a phosphane and CCl4 or CHCl3 to (VII), and either f1) reacting VII with NH3 in the presence of a catalyst to the compound of formula (VIII); and g) reacting VIII in the presence of a base with a compound of formula (IX), to the compound of formula (I); or f2) reacting the compound of formula (VII), in the presence of a solvent, a base, a copper catalyst and at least one ligand with the compound of formula (IXa), to the compound of formula (I).

  本发明涉及一种制备式(I)化合物的方法，该方法包括a)在惰性气氛下将式(II)化合物（其中X为氯或溴）与有机金属物种反应，得到式(X)的卤代苯基，将所得的式X卤代苯基与环戊二烯反应得到式(III)，b)在惰性溶剂存在下，将III与氧化剂反应得到式(IV)，c)在路易斯酸和氢化物源存在下，将IV反应得到式(V)，d)在氧化剂、碱和惰性溶剂存在下，将V反应得到式(VI)，e)在膦和CCl4或CHCl3存在下，将VI转化为式(VII)，并且f1)在催化剂存在下，将VII与NH3反应得到式(VIII)，并且g)在碱存在下，将VIII与式(IX)化合物反应得到式(I)化合物；或f2)在溶剂、碱、铜催化剂和至少一种配体存在下，将式(VII)与式(IXa)化合物反应得到式(I)化合物。
• [EN] PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'AMIDES D'ACIDE PYRAZOLECARBOXYLIQUE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011131544A1

  公开（公告）日：2011-10-27

  The invention relates to a process for the preparation of a compound of formula (I), which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species to (III) reacting the halobenzyne of formula (III) so formed with (IV) wherein R1 and R2 are hydrogen or C1-C6alkyl; to (V), b) hydrogenating V in the presence of a metal catalyst to (VI), c) ozonising (VI) to (VII) d) converting (VII) in the presence of a phosphane and CCI4 or CHCI3 to (VIII) (VIII), and either e1 ) reacting VIII with NH3 in the presence of a catalyst to (IX) and f) reacting IX in the presence of a base with the compound of formula (X), to the compound of formula (I); or e2) reacting the compound of formula (VIII), in the presence of a solvent, a base, a copper catalyst and at least one ligand with (Xa), to the compound of formula (I).

  本发明涉及一种制备式(I)化合物的方法，该方法包括a)将式(II)化合物与有机金属物种反应，其中X为氯或溴，得到式(III)；b)在金属催化剂存在下，对V进行氢化得到式(VI)；c)将(VI)臭氧化为(VII)；d)在膦和CCI4或CHCI3存在下将(VII)转化为(VIII)，其中R1和R2为氢或C1-C6烷基；e1)在催化剂存在下，将VIII与NH3反应得到(IX)，并在碱存在下将IX与式(X)化合物反应，得到式(I)化合物；或e2)在溶剂、碱、铜催化剂和至少一种配体存在下，将式(VIII)与(Xa)反应，得到式(I)化合物。
• PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES
  申请人：Gribkov Denis

  公开号：US20130035495A1

  公开（公告）日：2013-02-07

  The invention relates to a process for the preparation of formula (I) which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species to (III), wherein X is chloro or bromo; reacting the halobenzyne with a fulvene (IV), to a compound of formula (V) wherein X is chloro or bromo; b) hydrogenating V in the presence of a suitable metal catalyst to a compound of formula (VI) wherein X is chloro or bromo; and either c1) reacting the compound of formula VI with NH3 in the presence of a catalyst comprising palladium and at least one ligand to the compound of formula (VII); and d) reacting the compound of formula VII in the presence of a base with a compound of formula (VIII), to the compound of formula I; or c2 reacting the compound of formula (VI) in the presence of a copper catalyst and a ligand with the compound of formula (VIIIa), to the compound of formula (I).

  本发明涉及一种制备式（I）的方法，该方法包括a）将式（II）的化合物与有机金属物种反应成式（III），其中X为氯或溴；将卤代苯与富烯（IV）反应成式（V），其中X为氯或溴；b）在适当的金属催化剂存在下氢化V成式（VI），其中X为氯或溴；并且c1）在钯和至少一种配体组成的催化剂存在下将式VI的化合物与NH3反应成式（VII）；并且d）在碱存在下将式VII的化合物与式（VIII）的化合物反应成式I；或者c2）在铜催化剂和配体存在下将式VI的化合物与式（VIIIa）的化合物反应成式I。
• Process for the preparation of pyrazole carboxylic acid amides
  申请人：Gribkov Denis

  公开号：US08519151B2

  公开（公告）日：2013-08-27

  The invention relates to a process for the preparation of formula (I) which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species to (III), wherein X is chloro or bromo; reacting the halobenzyne with a fulvene (IV), to a compound of formula (V) wherein X is chloro or bromo; b) hydrogenating V in the presence of a suitable metal catalyst to a compound of formula (VI) wherein X is chloro or bromo; and either c1) reacting the compound of formula VI with NH3 in the presence of a catalyst comprising palladium and at least one ligand to the compound of formula (VII); and d) reacting the compound of formula VII in the presence of a base with a compound of formula (VIII), to the compound of formula I; or c2 reacting the compound of formula (VI) in the presence of a copper catalyst and a ligand with the compound of formula (VIIIa), to the compound of formula (I).

  该发明涉及一种制备式(I)的过程，该过程包括：a)将式(II)的化合物（其中X为氯或溴）与有机金属物种反应，得到式(III)（其中X为氯或溴）；将卤代苯炔与富勒烯(IV)反应，得到式(V)的化合物（其中X为氯或溴）；b)在适当的金属催化剂存在下，将V加氢，得到式(VI)的化合物（其中X为氯或溴）；并且c1)在钯和至少一种配体组成的催化剂存在下，将式VI的化合物与NH3反应，得到式(VII)的化合物；并且d)在碱存在下，将式VII的化合物与式(VIII)的化合物反应，得到式(I)的化合物；或者c2)在铜催化剂和配体存在下，将式VI的化合物与式(VIIIa)的化合物反应，得到式(I)的化合物。