cyano-fluorophenylacetamide | 794586-71-3

• 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: cyano-fluorophenylacetamide
• 英文别名: 2-Cyano-2-fluoro-2-phenylacetamide
• CAS: 794586-71-3
• 化学式: C₉H₇FN₂O
• 分子量: 178.166
• InChiKey: DJDUEHMSIPKSJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyano-fluorophenylacetamide 在 nitrosylsulfuric acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以72%的产率得到α-cyano-α-fluorophenylacetic acid
  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 伯吉斯试剂 、 氨 作用下， 以 乙腈 为溶剂， 生成 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

文献信息

• SEQUENCE OF 55 NEW FOUND PROTEINS AND THEIR APPLICATION
  申请人：Hoang Kieu

  公开号：US20140141488A1

  公开（公告）日：2014-05-22

  Sequence of 55 New Found Proteins—2 new proteins in Cryoprecipitate—8 new proteins in Fraction III—8 new proteins in Prothrombin Complex Concentrate—2 new found proteins in AFCC (Fraction 33)—3 new proteins in Fraction IV and 4 new found proteins in AFOD (Fraction 42)—2 in HemoRAAS®, 3 in FibroRAAS®, 5 in GammaRAAS®, 3 in AFCC®, 1 in Fraction 3-2, 2 in Fraction 3, 4 in FibingluRAAS® (Thrombin), 3 in AFOD®, 1 in AlbuRAAS®, 1 in FibingluRAAS® (High concentrate Fibrinogen), 1 in AFCC® (From fraction IV), 2 in Transferrin from Human Plasma and their name KH1 through KH55, and 16 existing proteins in which good KH healthy cells exists and their application.
• [EN] SEQUENCE OF 55 NEW FOUND PROTEINS AND THEIR APPLICATION<br/>[FR] SÉQUENCE DE 55 PROTÉINES NOUVELLEMENT DÉCOUVERTES ET LEUR APPLICATION
  申请人：HOANG KIEU

  公开号：WO2013116501A2

  公开（公告）日：2013-08-08

  Sequence of 55 New Found Proteins - 2 new proteins in Cryoprecipitate - 8 new proteins in Fraction III - 8 new proteins in Prothrombin Complex Concentrate - 2 new found proteins in AFCC [Fraction 33) - 3 new proteins in Fraction IV and 4 new found proteins in AFOD (Fraction 42) - 2 in HemoRAAS®, 3 in FibroRAAS®, 5 in GammaRAAS®, 3 in AFCC®, 1 in Fraction 3-2, 2 in Fraction 3, 4 in FibingluRAAS® (Thrombin), 3 in AFOD®, 1 in AlbuRAAS®, 1 in FibingluRAAS® (High concentrate Fibrinogen), 1 in AFCC® (From fraction IV), 2 in Transferrin from Human Plasma and their name KHl through KH55, and 16 existing proteins in which good KH healthy cells exists and their application.
• 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.