2-bromo-2, 2-difluoro-N-methyl-N-phenylacetamide | 2792-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-2, 2-difluoro-N-methyl-N-phenylacetamide
• 英文别名: 2-bromo-2,2-difluoro-N-methyl-N-phenylacetamide
• CAS: 2792-02-1
• 化学式: C₉H₈BrF₂NO
• 分子量: 264.069
• InChiKey: VXOOBCBXNYMPJL-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  232.8±40.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-2, 2-difluoro-N-methyl-N-phenylacetamide 在 dipotassium hydrogenphosphate 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以93%的产率得到3,3-difluoro-1-methylindolin-2-one
  参考文献：
  名称：

  Visible-light photoredox intramolecular difluoroacetamidation: facile synthesis of 3,3-difluoro-2-oxindoles from bromodifluoroacetamides

  摘要：

  已经通过可见光照射下的分子内氨基羰基二氟甲基自由基加成到芳烃的方式高效合成了3,3-二氟-2-氧代吲哚。

  DOI：

  10.1039/c5ob02121a
• 作为产物：
  描述：

  N-Methyl-N-<1,2,2-trifluor-vinyl>-anilin 生成 2-bromo-2, 2-difluoro-N-methyl-N-phenylacetamide
  参考文献：
  名称：

  Yakubovich,A.Ya. et al., Journal of general chemistry of the USSR, 1966, vol. 36, p. 1332 - 1339

  摘要：

  DOI：

文献信息

• Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: synthesis of quinazolinones containing the CF₂R group
  作者：Jin Yang、Bin Sun、Hao Ding、Pan-Yi Huang、Xiao-Li Tang、Rong-Cheng Shi、Zhi-Yang Yan、Chuan-Ming Yu、Can Jin

  DOI：10.1039/d0gc03761c

  日期：——

  A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the Csp3–Br bond homolysis of alkyl bromides via a substrate (quinazolinones)

  已经开发了一种新颖的光引发自催化的含未活化烯烃的喹唑啉酮的氟烷基化/环化反应，并带有各种氟烷基溴化物。相对于两个偶联配偶体，这种转化表现出优异的底物通用性。值得注意的是，这是第一个通过基质（喹唑啉酮）诱导的能量转移过程描述烷基溴化物的C sp 3 -Br键均质的例子。此外，温和的条件，对各种官能团的耐受性和操作简便性使该方案可用于合成含氟环稠合的喹唑啉酮。
• Copper-Catalyzed Cyclopropanol Ring Opening C_sp³–C_sp³ Cross-Couplings with (Fluoro)Alkyl Halides
  作者：Zhishi Ye、Kristen E. Gettys、Xingyu Shen、Mingji Dai

  DOI：10.1021/acs.orglett.5b03096

  日期：2015.12.18

  copper-catalyzed cyclopropanol ring opening cross-coupling reactions with difluoroalkyl bromides, perfluoroalkyl iodides, monofluoroalkyl bromides, and 2-bromo-2-alkylesters to synthesize various β-(fluoro)alkylated ketones are reported. The reactions feature mild conditions and excellent functional group compatibility and can be scaled up to gram scale. Preliminary mechanistic studies suggest the involvement

  报道了新型和通用的铜催化环丙醇与二氟烷基溴、全氟烷基碘、单氟烷基溴和2-溴-2-烷基酯的开环交叉偶联反应，合成各种β-(氟)烷基化酮。该反应条件温和，官能团相容性好，可放大至克级。初步的机理研究表明自由基中间体的参与。利用环丙醇开环产生的羰基，二氟烷基-烷基交叉偶联产物还可以很容易地转化为更有价值和更多样化的含偕二氟化合物。
• Novel heterocyclic compound
  申请人：Kodo Toru

  公开号：US20070191447A1

  公开（公告）日：2007-08-16

  A drug having a high affinity for benzodiazepine ω 3 receptors and showing curative and preventive effects for anxiety and depression, which comprises as the active ingredient, for example, a compound of the formula (1): wherein R 1 and R 2 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., R 3 and R 4 are independently a hydrogen atom, an optionally substituted alkyl group, etc., R 5 , R 6 , R 7 and R 8 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., X is an oxygen atom, a sulfur atom, NR 10 , etc. (in which R 10 is a hydrogen atom, an optionally substituted alkyl group, etc.)

  一种对苯二氮平ω3受体具有高亲和力，对焦虑和抑郁具有治疗和预防效果的药物，其包括作为活性成分的化合物，例如式（1）的化合物： 其中R1和R2分别为氢原子，可选取代烷基，可选取代芳基等； R3和R4分别为氢原子，可选取代烷基等； R5、R6、R7和R8分别为氢原子，可选取代烷基，可选取代芳基等； X为氧原子、硫原子、NR10等（其中R10为氢原子、可选取代烷基等）。
• Nickel/Photo-Cocatalyzed Three-Component Alkyl-Acylation of Aryl-Activated Alkenes
  作者：Pei Fan、Zhe Chen、Chuan Wang

  DOI：10.1021/acs.orglett.3c03669

  日期：2023.12.15

  with aldehydes and electron-withdrawing-group-activated alkyl bromides, providing straightforward access to various ketones under mild and ligand-free conditions. The photocatalyst TBADT plays a dual role in activating the acyl C–H bond of aldehydes via hydrogen atom transfer and reducing the C–Br bond of alkyl bromides via single-electron transfer. While the terminal C–C bond is forged through polarity-matched

  在此，我们公开了芳基取代的烯烃与醛和吸电子基团活化的烷基溴的镍/光共催化三组分烷基酰化，提供了在温和且无配体的条件下直接获得各种酮的方法。光催化剂TBADT发挥双重作用，通过氢原子转移激活醛的酰基C-H键，并通过单电子转移还原烷基溴的C-Br键。虽然末端 C-C 键是通过极性匹配的自由基型加成形成的，但镍可能参与酰化步骤。
• NOVEL HETEROCYCLIC COMPOUND
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1719761A1

  公开（公告）日：2006-11-08

  A drug having a high affinity for benzodiazepine ω3 receptors and showing curative and preventive effects for anxiety and depression, which comprises as the active ingredient, for example, a compound of the formula (1): wherein R1 and R2 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., R3 and R4 are independently a hydrogen atom, an optionally substituted alkyl group, etc., R5, R6, R7 and R8 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., X is an oxygen atom, a sulfur atom, NR10, etc. (in which R10 is a hydrogen atom, an optionally substituted alkyl group, etc.)

  一种对苯二氮卓ω3 受体具有高亲和力并对焦虑症和抑郁症具有治疗和预防作用的药物，其活性成分包括例如式（1）的化合物： 其中 R1 和 R2 独立地为氢原子、任选取代的烷基、任选取代的芳基等、 R3 和 R4 独立地为氢原子、任选取代的烷基等、 R5、R6、R7 和 R8 独立地为氢原子、任选取代的烷基、任选取代的芳基等、 X 是氧原子、硫原子、NR10 等（其中 R10 是氢原子、任选取代的烷基等）