(R)-2-fluoro-2-phenylacetyl chloride | 38345-65-2

• 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: (R)-2-fluoro-2-phenylacetyl chloride
• 英文别名: (R)-(-)-α-fluoro phenyl acetyl chloride；(R)-2-fluorophenylacetyl chloride；(R)-(-)-α-fluorophenylacetic acid；(2R)-2-fluoro-2-phenylacetyl chloride
• CAS: 38345-65-2
• 化学式: C₈H₆ClFO
• 分子量: 172.586
• InChiKey: VFWZIUUVUDYNJF-SSDOTTSWSA-N

物化性质

• 沸点：
  213.2±25.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

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：

  (R)-2-fluoro-2-phenylacetyl chloride 在 甲醇 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 N-{5-[(2R)-2-fluoro-2-phenylacetyl]-1H,4H,5H,6H-pyrrolo[3,4-c]pyrazol-3-yl}-4-(4-methylpiperazin-1-yl)benzamide
  参考文献：
  名称：

  1,4,5,6-Tetrahydropyrrolo[3,4-c]pyrazoles:  Identification of a Potent Aurora Kinase Inhibitor with a Favorable Antitumor Kinase Inhibition Profile

  摘要：

  The optimization of a series of 5-phenylacetyl 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole derivatives toward the inhibition of Aurora kinases led to the identification of compound 9d. This is a potent inhibitor of Aurora kinases that also shows low nanomolar potency against additional anticancer kinase targets. Based on its high antiproliferative activity on different cancer cell lines, favorable chemico-physical and pharmacokinetic properties, and high efficacy in in vivo tumor models, compound 9d was ultimately selected for further development.

  DOI：

  10.1021/jm060897w
• 作为产物：
  描述：

  2-氨基-2-苯基乙酸 在 氯化亚砜 、 氟化氢吡啶 、 sodium nitrite 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (R)-2-fluoro-2-phenylacetyl chloride
  参考文献：
  名称：

  Barrelle, Michel; Hamman, Sylvain, Journal of Chemical Research, Miniprint, 1990, # 4, p. 701 - 715

  摘要：

  DOI：

文献信息

• 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.
• Determination of the enantiomeric purity and the configuration of β-aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to β-blockers
  作者：Marcel Apparu、Younes Ben Tiba、Pierre-Marc Léo、Sylvain Hamman、Christian Coulombeau

  DOI：10.1016/s0957-4166(00)00254-8

  日期：2000.7

  A method has been developed for determining the enantiomeric purity and the absolute configuration of beta-aminoalcohols of type ArOCH2CH(OH)CH2NHR (R = iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The F-19 NMR analysis of the derivative obtained revealed the presence of two distinctly separate signals (similar to 2.5 ppm), the one for the RS-SR pair being the most deshielded. The configuration was determined directly on the aminoalcohol by using the acid. In stoichiometric conditions, when R = iPr, the amide function was obtained very preponderantly. The F-19 NMR spectrum of the amide presented four distinct signals when derivatization was carried out by means of a reaction between the (+/-)-beta-aminoalcohol and the (R)-AFPA. The extreme signals, which were over 3.5 ppm apart, did not belong to the same diastereomer. With R = tBu essentially the ester function was obtained. The first studies revealed the presence of two signals, though not as clearly separated as in the previous cases. Each experiment was simple to perform, and purification was not necessary. Mosher's acid gave unsatisfactory results in each case. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Acide 2-fluoro-2- phenylacetique. Partie 3 [1]. Correlation entre la configuration de ses amides d'amines chirales et les deplacements chimiques du proton et du fluor
  作者：S. Hamman

  DOI：10.1016/s0022-1139(00)84998-2

  日期：1990.12

  Proton and fluorine chemical shifts of amides from PhCHFCO2H (used as a chiral derivatizing agent) and amines L1CH(NH2)L2 are correlated with configuration in order to assign configuration of chiral amines by F-19 NMR spectroscopy.
• 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
• Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M 2 receptors
  作者：Juliette Martin、Annamaria Deagostino、Cécile Perrio、François Dauphin、Christophe Ducandas、Christophe Morin、Paul-Louis Desbène、Marie Claire Lasne

  DOI：10.1016/s0968-0896(99)00307-7

  日期：2000.3

  Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carabonyl]-6H-pyrido[2,3- b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the alpha-highly sulphated cyclodextrin (alpha-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.