4-(溴甲基)二环[2.2.1]庚烷 | 61192-17-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 4-(溴甲基)二环[2.2.1]庚烷
• 英文名称: 1-(Bromomethyl)bicyclo<2.2.1>heptane
• 英文别名: 1-Bromomethyl-norbornan；1-Brommethyl-bicyclo<2.2.1>heptan；1-(Bromomethyl)bicyclo[2.2.1]heptane
• CAS: 61192-17-4
• 化学式: C₈H₁₃Br
• mdl: MFCD20624214
• 分子量: 189.095
• InChiKey: AWCGALZJVRGRBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  4-(溴甲基)二环[2.2.1]庚烷 在 三正丁基氢锡 作用下， 反应 1.0h， 生成 4-甲基二环[2.2.1]庚烷
  参考文献：
  名称：

  Synthesis of bridgehead-substituted bicyclo[2.2.1]heptanes by radical cyclization

  摘要：

  A kinetic investigation shows that the rate of cyclization (k(C)) of the (4-methylenecyclohexyl)methyl radical 3 at 25-degrees-C is 4.4 x 10(2) s-1, which is considerably slower than that (2.3 x 10(5) s-1) of the parent 5-hexenyl radical. The energy of activation for the process 3 - 4 is 12.8 kcal mol-1, which is in excellent agreement with theoretical values derived from force-field calculations. Ring-closure of appropriately substituted (4-methylenecyclohexyl)methyl radical precursors allows the synthesis of bicyclo[2.2.1]heptyl systems with useful functionality at the bridgehead to be achieved readily and in high yield. An interesting example is given of the application of an iodine-atom-transfer cyclization to the synthesis of a bicyclo[2.2.1]heptane functionalized at C7 and C1.

  DOI：

  10.1021/jo00060a029
• 作为产物：
  描述：

  1-(羟甲基)双环(2.2.1)庚烷 在 吡啶 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 144.0h， 生成 4-(溴甲基)二环[2.2.1]庚烷
  参考文献：
  名称：

  Synthesis of bridgehead-substituted bicyclo[2.2.1]heptanes by radical cyclization

  摘要：

  A kinetic investigation shows that the rate of cyclization (k(C)) of the (4-methylenecyclohexyl)methyl radical 3 at 25-degrees-C is 4.4 x 10(2) s-1, which is considerably slower than that (2.3 x 10(5) s-1) of the parent 5-hexenyl radical. The energy of activation for the process 3 - 4 is 12.8 kcal mol-1, which is in excellent agreement with theoretical values derived from force-field calculations. Ring-closure of appropriately substituted (4-methylenecyclohexyl)methyl radical precursors allows the synthesis of bicyclo[2.2.1]heptyl systems with useful functionality at the bridgehead to be achieved readily and in high yield. An interesting example is given of the application of an iodine-atom-transfer cyclization to the synthesis of a bicyclo[2.2.1]heptane functionalized at C7 and C1.

  DOI：

  10.1021/jo00060a029

文献信息

• HETEROCYCLIC P2X7 ANTAGONISTS
  申请人：AXXAM S.p.A.

  公开号：EP3398941A1

  公开（公告）日：2018-11-07

  The present invention refers to compounds, and to pharmaceutical compositions containing said compounds, of the following formula (I) or a pharmaceutically acceptable salt thereof: including any stereochemically isomeric form thereof, wherein: R1 is independently selected from the group consisting of aliphatic, aromatic or heteroaromatic ring, optionally substituted by one or more substituents chosen from the group consisting of C1-C4 alkyl optionally substituted by one or more halogen atom(s), halogen, C1-C4 alkoxy; R2 is independently selected from the group consisting of aliphatic, heteroaliphatic, aromatic or heteroaromatic ring, bicyclic aliphatic, heteroaromatic or aromatic ring, C1-C6 alkyl, alkenyl or alkynyl chain, optionally substituted by one or more substituents chosen from the group consisting of C1-C4 alkyl optionally substituted by one or more halogen atom(s), halogen, C1-C4 alkoxy, cyano, C1-C4 alkylthio, SO-C1-C4 alkyl, SO2-C1-C4 alkyl, N(C1-C4 alkyl)2; n is 0, 1 or 2; R3 and R4 can be, independently, -H, -F, C1-C4 alkyl, -OH, -OC1-C4 alkyl; X is O, S, CH2, CH-C1-C4 alkyl, -NH or -NC1-C4 alkyl; R5 is -H or -CH3 optionally substituted by one or more fluorine atoms. The compounds of the invention can be used in treatment of conditions or diseases mediated by P2X7 receptor.

  本发明涉及化合物及含有所述化合物的药物组合物，其化学式为(I)或其药学上可接受的盐：包括其立体化异构体形式，其中：R1独立地选自由由脂肪烃、芳香烃或杂芳环组成的基团，可选择地被来自由由C1-C4烷基、可选择地被一个或多个卤原子取代的卤素、卤素、C1-C4烷氧基的一个或多个取代基替代；R2独立地选自由由脂肪烃、杂脂肪烃、芳香烃或杂芳环、双环脂肪烃、杂芳烃或芳香环、C1-C6烷基、烯基或炔基链组成的基团，可选择地被来自由由C1-C4烷基、可选择地被一个或多个卤原子取代的卤素、卤素、C1-C4烷氧基、氰基、C1-C4烷硫基、SO-C1-C4烷基、SO2-C1-C4烷基、N(C1-C4烷基)2的一个或多个取代基替代；n为0、1或2；R3和R4可以独立地为-H、-F、C1-C4烷基、-OH、-OC1-C4烷基；X为O、S、CH2、CH-C1-C4烷基、-NH或-NC1-C4烷基；R5为-H或-CH3，可选择地被一个或多个氟原子取代。本发明的化合物可用于治疗通过P2X7受体介导的疾病或症状。
• [EN] A PROCESS OF A QUATERNARY AMMONIUM SALT USING PHOSPHATE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN SEL D'AMMONIUM QUATERNAIRE À L'AIDE D'UN PHOSPHATE
  申请人：DAINIPPON SUMITOMO PHARMA CO

  公开号：WO2011136384A1

  公开（公告）日：2011-11-03

  The present invention relates to a novel process for preparing quaternary ammonium salt derivatives.

  本发明涉及一种制备季铵盐衍生物的新工艺。
• <b>Strained Small Ring Compounds: Bridgehead Substituted Bicyclo [2.1.1]hexanes</b>
  作者：Kenneth B. Wiberg、Betty R. Lowry

  DOI：10.1021/ja00903a031

  日期：1963.10
• A PROCESS OF A QUATERNARY AMMONIUM SALT USING PHOSPHATE
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP2563791A1

  公开（公告）日：2013-03-06
• [EN] HETEROCYCLIC P2X7 ANTAGONISTS<br/>[FR] ANTAGONISTES HÉTÉROCYCLIQUES DE P2X7
  申请人：AXXAM SPA

  公开号：WO2018202694A1

  公开（公告）日：2018-11-08

  The present invention refers to compounds of the following formula (I) or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions containing them and to a process for the preparation of said compounds: Formula (I), wherein: R1 is independently selected from hydrogen atom, amine group, monocyclic or bicyclic aliphatic, aromatic, heteroaliphatic or heteroaromatic ring, optionally substituted by one or more substituents selected from C1-C4 alkyl optionally substituted by one or more halogen atom(s), halogen, C1-C4 alkoxy or phenyl group, optionally substituted by C1-C4 alkyl; R2 is independently selected from monocyclic or bicylic aliphatic, heteroaliphatic, aromatic or heteroaromatic ring, C1-C6 alkyl, alkenyl or alkynyl chain, optionally substituted by one or more substituents selected from C1-C4 alkyl optionally substituted by one or more halogen atom(s), halogen, C1-C4 alkoxy, cyano, C1-C4 alkylthio, SO-C1-C4 alkyl, SO2-C1-C4 alkyl, N(C1-C4 alkyl)2; n is 1 or 2; preferably n is 1; m is 0, 1 or 2; preferably m is 0; R3 and R4 can be, independently, -H, -F, C1-C4 alkyl, -OH, -OC1-C4 alkyl; preferably they are both -H; X is O or S; R5 is -H or -CH3 optionally substituted by one or more fluorine atoms; preferably R5 is hydrogen. The compounds of the invention can be used in the treatment of conditions or diseases mediated by P2X7 receptor.