5,5-difluoro-2-methyl-2-pentene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 5,5-difluoro-2-methyl-2-pentene
• 英文别名: 5,5-Difluoro-2-methylpent-2-ene
• 化学式: C₆H₁₀F₂
• 分子量: 120.142
• InChiKey: ADLBHXQSAPKGSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  difluoromethyl copper 、 1-氯-3-甲基-2-丁烯 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以80%的产率得到5,5-difluoro-2-methyl-2-pentene
  参考文献：
  名称：

  The preparation of HCF2CdX and HCF2ZnX via direct insertion into the carbon halogen bond of CF2HY (Y=Br, I)

  摘要：

  The difluoromethylcadmium and zinc reagents have been prepared in DMF via direct insertion of Cd-0 into the carbon halogen bond of CF2HY (Y = Br, I). These reagents are stable at 65-75 degrees C and exhibit prolonged stability and activity at room temperature. Metathesis of the difluoromethylcadmium reagents with Cu(I)X (X = Br, Cl) at -55 degrees C rapidly produces difluoromethylcopper. The copper reagent is significantly less stable than the cadmium or zinc reagent and rapidly decomposes at room temperature. The difluoromethylcadmium and copper reagents exhibit good reactivity with allylic halides, propargylic derivatives and 1-iodoalkynes to provide good yields of the corresponding difluoromethylalkenes, difluoromethylallenes and difluoromethyl-2-alkynes. Alkylation is successful only with reactive alkyl halides. Generally, the difluoromethylcopper reagent is more reactive than the difluoromethylcadmium reagent and generally exhibits higher regioselectivity in reactions that can occur by either alpha- or -gamma-attack. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.05.015

文献信息

• FLUORINATED 1,4-DISUBSTITUTED PIPERIDINE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0930298A1

  公开（公告）日：1999-07-21

  This invention relates to novel fluorine-containing 1,4-disubstituted piperidine derivatives represented by a general formula [I] and pharmaceutically acceptable salts thereof, [wherein: Ar represents an aryl group or a hetero-aryl group having 1 to 2 hetero atoms selected from a group consisting of nitrogen, oxygen and sulfur (any 1 to 3 hydrogen atoms on the ring of said aryl or heteroaryl group may be substituted with lower alkyl, etc.); R1 represents C3-C6 cycloalkyl whose any 1-4 hydrogen atmos may be substituted with fluorine atoms(s); R2 represents C5-C15 saturated or unsaturated aliphatic hydrocarbon groups whose any 1 to 6 hydrogen atoms may be substituted with fluorine atom(s), aralkyl, arylalkenyl, heteroarylalkyl or heteroarylalkenyl group having 1 to 2 hetero atoms selected from a group consisting of nitrogen, oxygen and sulfur (optionally any 1 to 3 hydrogen atoms on the ring in said aralkyl, arylalkenyl, hetero-arylalkyl or heteroarylalkenyl group may be substituted with lower alkyl, trifluoromethyl, cyano, hydroxyl, nitro, lower alkoxycarbonyl, halogen, lower alkoxy or amino, etc. ; and X stands for O or NH, provided that at least either one of R1 and R2 contains one or more fluorine atoms]. The compounds of the present invention have selective antagonistic activity for muscarinic M3 receptors, and exhibit excellent oral activity, duration of action and pharmacokinetics, so that they have little side effects and are safe and effective. Therefore they are useful for treatment or prophylaxis of respiratory diseases, urinary diseases and digestive diseases.

  本发明涉及通式[I]代表的新型含氟 1,4-二取代哌啶衍生物 及其药学上可接受的盐类、 其中 Ar 代表芳基或杂芳基，其 1 至 2 个杂原子选自氮、氧和硫组成的组 (所述芳基或杂芳基环上的任何 1 至 3 个氢原子可被低级烷基等取代)； R1 代表 C3-C6 环烷基，其任意 1-4 个氢原子可被氟原子取代； R2 代表 C5-C15 饱和或不饱和脂肪族烃基，其任意 1-6 个氢原子可被氟原子取代；R3 代表芳烷基、芳烯基、杂芳烷基或杂芳基烯基，其 1-2 个杂原子选自由氮、氧和硫组成的组、氧和硫（上述芳烷基、芳烯基、杂芳烷基或杂芳基烯基的环上任意 1 至 3 个氢原子可任选被低级烷基、三氟甲基、氰基、羟基、硝基、低级烷氧基羰基、卤素、低级烷氧基或氨基等取代）；以及和 X 代表 O 或 NH、 条件是 R1 和 R2 中至少有一个含有一个或多个氟原子]。 本发明的化合物对毒蕈碱类 M3 受体具有选择性拮抗活性，并表现出良好的口服活性、作用持续时间和药代动力学，因此副作用小且安全有效。因此，它们可用于治疗或预防呼吸系统疾病、泌尿系统疾病和消化系统疾病。
• The preparation and allylation of difluoromethylcadmium
  作者：Greg A. Hartgraves、Donald J. Burton

  DOI：10.1016/s0022-1139(00)81613-9

  日期：1988.6
• US5948792A
  申请人：——

  公开号：US5948792A

  公开（公告）日：1999-09-07
• US6040449A
  申请人：——

  公开号：US6040449A

  公开（公告）日：2000-03-21
• The preparation of HCF2CdX and HCF2ZnX via direct insertion into the carbon halogen bond of CF2HY (Y=Br, I)
  作者：Donald J. Burton、Greg A. Hartgraves

  DOI：10.1016/j.jfluchem.2007.05.015

  日期：2007.10

  The difluoromethylcadmium and zinc reagents have been prepared in DMF via direct insertion of Cd-0 into the carbon halogen bond of CF2HY (Y = Br, I). These reagents are stable at 65-75 degrees C and exhibit prolonged stability and activity at room temperature. Metathesis of the difluoromethylcadmium reagents with Cu(I)X (X = Br, Cl) at -55 degrees C rapidly produces difluoromethylcopper. The copper reagent is significantly less stable than the cadmium or zinc reagent and rapidly decomposes at room temperature. The difluoromethylcadmium and copper reagents exhibit good reactivity with allylic halides, propargylic derivatives and 1-iodoalkynes to provide good yields of the corresponding difluoromethylalkenes, difluoromethylallenes and difluoromethyl-2-alkynes. Alkylation is successful only with reactive alkyl halides. Generally, the difluoromethylcopper reagent is more reactive than the difluoromethylcadmium reagent and generally exhibits higher regioselectivity in reactions that can occur by either alpha- or -gamma-attack. (C) 2007 Elsevier B.V. All rights reserved.