2-Fluor-2-phenylmalonamid | 1547-97-3

• 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-Fluor-2-phenylmalonamid
• 英文别名: 2-Fluor-2-phenylmalondiamid；2-Fluor-2-phenyl-malonsaeure-diamid；fluoro-phenyl-malonic acid diamide；Fluor-phenyl-malonsaeure-diamid；2-Fluoro-2-phenylpropanediamide
• CAS: 1547-97-3
• 化学式: C₉H₉FN₂O₂
• 分子量: 196.181
• InChiKey: UDDFTUHEZQVJCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Fluor-2-phenylmalonamid 在 伯吉斯试剂 作用下， 以 乙腈 为溶剂， 以80%的产率得到cyano-fluorophenylacetamide
  参考文献：
  名称：

  Realization of the synthesis of α,α-disubstituted carbamylacetates and cyanoacetates by either enzymatic or chemical functional group transformation, depending upon the substrate specificity of Rhodococcus amidase

  摘要：

  Substrate specificity and enantioselectivity of nitrile hydratase and amidase from R. rhodochrous IFO 15564 has been studied by applying a series of alpha,alpha-disubstituted malononitriles and related substrates. The amidase preferentially hydrolyzed the pro-(R) carbamyl group (amide) of the prochiral diamides, an intermediate resulting from the action of nitrile hydratase in a nonenantiotopic group-selective manner. The introduction of a fluorine atom at the alpha-position caused an inhibitory effect on amidase. By a combination of this microbial transformation and the subsequent Hofmann rearrangement, an important precursor of (S)methyldopa with 98.4% ee has been prepared. For the enzymatically poor substrate, the action on HO3SONO-H2O on the carbamyl group was effective, leaving the cyano group intact. This conversion is demonstrated as the key step for the expeditious preparation of (+/-)-alpha-cyano-alpha-fluoro-alpha-phenylacetic acid (CFPA) from diethyl alpha-fluoro-alpha-phenylmalonate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.047
• 作为产物：
  描述：

  diethyl 2-fluoro-2-phenylmalonate 在 氨 、 sodium amide 作用下， 生成 2-Fluor-2-phenylmalonamid
  参考文献：
  名称：

  Reactions of Perchloryl Fluoride with Organic Compounds. II. Fluorination of Certain Active Methylene Compounds¹

  摘要：

  DOI：

  10.1021/ja01557a019

文献信息

• Reactions of Perchloryl Fluoride with Organic Compounds. II. Fluorination of Certain Active Methylene Compounds¹
  作者：C. E. Inman、R. E. Oesterling、E. A. Tyczkowski

  DOI：10.1021/ja01557a019

  日期：1958.12
• PYRROLOTRIAZINE KINASE INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1761268A2

  公开（公告）日：2007-03-14
• EP1761268A4
  申请人：——

  公开号：EP1761268A4

  公开（公告）日：2009-07-08
• [EN] PYRROLOTRIAZINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE A BASE DE PYRROLOTRIAZINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2006004833A2

  公开（公告）日：2006-01-12

  In general, the instant invention comprises compounds of Formulas I and II including pharmaceutically acceptable salts thereof. The compounds of the invention are useful as protein kinase inhibitors and therefore are useful for treating cancer and other protein kinase mediated diseases.
• Realization of the synthesis of α,α-disubstituted carbamylacetates and cyanoacetates by either enzymatic or chemical functional group transformation, depending upon the substrate specificity of Rhodococcus amidase
  作者：Masahiro Yokoyama、Mieko Kashiwagi、Masakazu Iwasaki、Ken-ichi Fuhshuku、Hiromichi Ohta、Takeshi Sugai

  DOI：10.1016/j.tetasy.2004.04.047

  日期：2004.9

  Substrate specificity and enantioselectivity of nitrile hydratase and amidase from R. rhodochrous IFO 15564 has been studied by applying a series of alpha,alpha-disubstituted malononitriles and related substrates. The amidase preferentially hydrolyzed the pro-(R) carbamyl group (amide) of the prochiral diamides, an intermediate resulting from the action of nitrile hydratase in a nonenantiotopic group-selective manner. The introduction of a fluorine atom at the alpha-position caused an inhibitory effect on amidase. By a combination of this microbial transformation and the subsequent Hofmann rearrangement, an important precursor of (S)methyldopa with 98.4% ee has been prepared. For the enzymatically poor substrate, the action on HO3SONO-H2O on the carbamyl group was effective, leaving the cyano group intact. This conversion is demonstrated as the key step for the expeditious preparation of (+/-)-alpha-cyano-alpha-fluoro-alpha-phenylacetic acid (CFPA) from diethyl alpha-fluoro-alpha-phenylmalonate. (C) 2004 Elsevier Ltd. All rights reserved.