1-(bromomethyl)-1-fluorocyclohexane | 17171-00-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1-(bromomethyl)-1-fluorocyclohexane
• 英文别名: 1-(Bromomethyl)-1-fluorocyclohexane
• CAS: 17171-00-5
• 化学式: C₇H₁₂BrF
• mdl: MFCD20623965
• 分子量: 195.075
• InChiKey: PXTZBNRAAFANNT-UHFFFAOYSA-N

物化性质

• 熔点：
  47 °C
• 沸点：
  47 °C(Press: 1 Torr)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  1-(bromomethyl)-1-fluorocyclohexane 在 sodium azide 、 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以53%的产率得到1-azidomethyl-1-fluorocyclohexane
  参考文献：
  名称：

  A convenient approach towards the 1-aminomethyl-1-fluorocycloalkane scaffold

  摘要：

  A three-step synthesis towards 1-aminomethy1-1-fluorocycloalkanes was developed starting from methylenecycloalkanes. Methylenecyclobutane, methylenecyclopentane and methylenecyclohexane were first bromofluorinated to provide the corresponding Markovnikov products, 1-bromomethy1-1-fluorocycloalkanes, which were then converted towards the title compound via azide substitution and hydrogenation. The bromofluorination of methylenecyclopropane, however, led to both the Markovnikov and the anti-Markovnikov product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.127
• 作为产物：
  描述：

  亚甲基环己烷 在 N-溴代丁二酰亚胺(NBS) 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到1-(bromomethyl)-1-fluorocyclohexane
  参考文献：
  名称：

  富含sp3的β-氟磺酰氯的合成

  摘要：

  报道了从烯烃开始合成富含sp 3的β-氟磺酰氯的三步法。该方法已成功应用于带有环外或环内双键的各种无环和环状底物。该方法适用于多种底物，并能耐受许多官能团和保护基团。此外，以克数级的单环顺式非对映体形式获得目标环状化合物。标题化合物是用于药物发现的有希望的基础，可用于获得富含sp 3的β-氟和α，β-不饱和磺酰胺。

  DOI：

  10.1055/s-0040-1706101

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。
• Generation of Interhalogen Fluorides under Mild Conditions:  A Comparison of Sluggish and Reactive Interhalogen Fluorides
  作者：Dale F. Shellhamer、Mark J. Horney、Benjamin J. Pettus、Tobiah L. Pettus、Joy Merry Stringer、Victor L. Heasley、Robert G. Syvret、John M. Dobrolsky

  DOI：10.1021/jo972319g

  日期：1999.2.1

  Interhalogen fluorides (XF; X = I, Br, or Cl) generated from xenon difluoride (XeF2) or triethylamine trihydrofluoride (TREAT HF) with iodine (I-2), N-halosuccinimides (NXS; X = I, Br, or CI), or alkylhypohalites (ROX; R = CH3 or t-Bu, X = Br or Cl) with alkenes and aromatics are reported. A comparison of the above reactions with other methods reported in the literature to generate interhalogen fluorides is made. Interhalogens generated from direct action of elemental fluorine (F-2) or XF3 (X = I, Br, or Cl) with chlorine (Cl-2), bromine (Br-2), or iodine (I-2) give a species that can react with electron-deficient alkenes or aromatics. These reagents are too reactive for electron-rich substrates. Interhalogen fluorides from reagents like NXS or ROX with XeF2 or amine HF are much less reactive and give good yields with electron-rich akenes or aromatics.
• ACRYLIC ACID DERIVATIVE, PREPARATION METHOD AND USE IN MEDICINE THEREOF
  申请人：Zhejiang Hisun Pharmaceutical Co., Ltd.

  公开号：EP3378861B1

  公开（公告）日：2021-08-04
• [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.