(S)-(+)-α-fluorophenylacetic acid | 38345-68-5

• 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: (S)-(+)-α-fluorophenylacetic acid
• 英文别名: (S)-α-fluorophenylacetyl chloride；(S)-alpha-fluorophenylacetyl chloride；(2S)-2-fluoro-2-phenylacetyl chloride
• CAS: 38345-68-5
• 化学式: C₈H₆ClFO
• 分子量: 172.586
• InChiKey: VFWZIUUVUDYNJF-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-benzyl-3-(benzylamino)pyrrolidine 、 (S)-(+)-α-fluorophenylacetic acid 在 甲基锂 作用下， 生成
  参考文献：
  名称：

  Handy access to chiral N,N′-disubstituted 3-aminopyrrolidines.

  摘要：

  A new and rapid synthesis of (S)-3-aminopyrrolidines 7 is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the Z-protecting group, is converted to corresponding imines and readily reduced to disubstituted chiral 3-aminopyrrolidines 7. Almost no racemization (less-than-or-equal-to 5%) of the original amino-acid asymmetric center may be observed.

  DOI：

  10.1016/s0957-4166(00)82081-9
• 作为产物：
  描述：

  (S)-2-fluoro-2-phenylacetic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (S)-(+)-α-fluorophenylacetic acid
  参考文献：
  名称：

  Acide fluoro-2 phenyl-2 acetique: Synthesis, configuration absolute et emploi comme agent chiral de derivation

  摘要：

  DOI：

  10.1016/s0022-1139(00)83089-4

文献信息

• Isoindolone derivatives, their preparation and the pharmaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US05102667A1

  公开（公告）日：1992-04-07

  This invention relates to isoindolone derivatives of general formula (I) in which the radicals R are hydrogen atoms or together form a bond, the symbols R' are phenyl radicals which can be substituted by a halogen atom or a methyl radical in position 2 or 3, X is an oxygen or sulphur atom or a radical N--R.sub.3, R.sub.3 being H, optionally substituted alkyl or dialkylamino, R.sub.1 is optionally substituted phenyl or cyclohexadienyl, naphthyl or a heterocycle and R.sub.2 is H, halogen, OH, alkyl, amionoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, acyloxy, carboxyl, optionally substituted alkoxycarbonyl, benzyloxycarbonyl, amino or acylamino, in their (3aR,7aR) forms or in the (3aRS,7aRS) form or their mixtures, and if appropriate their salts where such exist, and their preparation. The new derivatives according to the invention are particularly valuable as antagonists of substance P. ##STR1##

  本发明涉及通式(I)的异吲哚酮衍生物，其中基团R为氢原子或共同形成一个键，符号R'为可被卤素原子或甲基在2或3位取代的苯基基团，X为氧或硫原子或基团N--R.sub.3，R.sub.3为H，可选择性取代的烷基或二烷基氨基，R.sub.1为可选择性取代的苯基或环己二烯基，萘基或杂环，R.sub.2为H，卤素，OH，烷基，氨基烷基，烷基氨基烷基，二烷基氨基烷基，烷氧基，烷基硫基，酰氧基，羧基，可选择性取代的烷氧羰基，苄氧羰基，氨基或酰氨基，在其(3aR,7aR)形式或(3aRS,7aRS)形式或其混合物中，以及如果存在的话，它们的盐，以及它们的制备方法。根据本发明的新衍生物特别有价值作为P物质拮抗剂。 ##STR1##
• From Bifunctional to Trifunctional (Tricomponent Nucleophile–Transition Metal–Lewis Acid) Catalysis: The Catalytic, Enantioselective α-Fluorination of Acid Chlorides
  作者：Jeremy Erb、Daniel H. Paull、Travis Dudding、Lee Belding、Thomas Lectka

  DOI：10.1021/ja2014345

  日期：2011.5.18

  fluorination of a ketene enolate intermediate. We discovered, for the first time, that a third catalyst, a Lewis acidic lithium salt, could be introduced into a dually activated system to amplify yields of aliphatic products, primarily through activation of the fluorinating agent. Through our mechanistic studies (based on kinetic data, isotopic labeling, spectroscopic measurements, and theoretical calculations)

  我们详细报告了我们对酰氯的催化不对称 α-氟化的研究，这是一种生产一系列 α-氟代羧酸衍生物的实用方法，其中通过烯酮烯醇中间体的亲电氟化来控制提高的产率和几乎完全的对映选择性. 我们第一次发现，可以将第三种催化剂路易斯酸性锂盐引入双重活化系统，主要通过氟化剂的活化来提高脂肪族产物的产量。通过我们的机理研究（基于动力学数据、同位素标记、光谱测量和理论计算），我们能够利用我们对这种“三功能”的理解
• US5102667A
  申请人：——

  公开号：US5102667A

  公开（公告）日：1992-04-07
• Handy access to chiral N,N′-disubstituted 3-aminopyrrolidines.
  作者：Jacques Maddaluno、Aline Corruble、Valéric Leroux、Gérard Plé、Pierre Duhamel

  DOI：10.1016/s0957-4166(00)82081-9

  日期：1992.10

  A new and rapid synthesis of (S)-3-aminopyrrolidines 7 is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the Z-protecting group, is converted to corresponding imines and readily reduced to disubstituted chiral 3-aminopyrrolidines 7. Almost no racemization (less-than-or-equal-to 5%) of the original amino-acid asymmetric center may be observed.
• Acide fluoro-2 phenyl-2 acetique: Synthesis, configuration absolute et emploi comme agent chiral de derivation
  作者：S. Hamman、M. Barrelle、F. Tetaz、C.G. Beguin

  DOI：10.1016/s0022-1139(00)83089-4

  日期：1987.10