phenylmethyl 3--2(R)-fluoropropanoate | 82770-45-4

• 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: phenylmethyl 3--2(R)-fluoropropanoate
• 英文别名: benzyl (2R)-3-(dibenzylamino)-2-fluoropropanoate
• CAS: 82770-45-4
• 化学式: C₂₄H₂₄FNO₂
• 分子量: 377.458
• InChiKey: LWZWKAWTHAMCLH-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenylmethyl 3--2(R)-fluoropropanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以93%的产率得到(R)-3-(dibenzylamino)-2-fluoropropanoic acid
  参考文献：
  名称：

  Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

  摘要：

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.

  DOI：

  10.1021/jm00080a005
• 作为产物：
  描述：

  N,N-二苯甲基-L-丝氨酸苯甲酯 、 二乙胺基三氟化硫 以90%的产率得到
  参考文献：
  名称：

  SOMEKH, L.;SHANZER, A., J. AMER. CHEM. SOC., 1982, 104, N 21, 5836-5837

  摘要：

  DOI：

文献信息

• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE FLUOROAMINE
  申请人：Central Glass Company, Limited

  公开号：EP2243769B1

  公开（公告）日：2017-06-28
• Process for Producing Alpha-Fluoro-Beta-Amino Acids
  申请人：Ishii Akihiro

  公开号：US20110015428A1

  公开（公告）日：2011-01-20

  By reacting a β-hydroxy-α-amino acid with sulfuryl fluoride (SO 2 F 2 ) in the presence of an organic base, it is possible to produce an α-fluoro-β-amino acid of the formula [2]. By using a C8-12 tertiary amine having two or more alkyl groups of C3 or higher, and especially diisopropylethylamine, as the organic base, by-production of quantery ammonium salts is effectively suppressed. By applying the production process of the present invention, it is possible to very easily produce (2R)-3-(dibenzylamino)-2-fluoropropionic acid methyl ester, which is extremely important as a pharmaceutical intermediate, with high positional selectivity even on an industrial scale.
• Process for Production of Optically Active Fluoroamine
  申请人：Ishii Akihiro

  公开号：US20110034732A1

  公开（公告）日：2011-02-10

  Disclosed is a process for producing a protected optically active fluoroamine, which comprises the step of reacting an imine-protected optically active hydroxyamine, an oxazolidine-protected optically active hydroxyamine, or a mixture of the imine-protected optically active hydroxyamine and the oxazolidine-protected optically active hydroxyamine, with sulfuryl fluoride (SO 2 F 2 ) in the presence of a tertiary amine having a carbon number of 7 to 18 (produced by substituting all of three hydrogen atoms in ammonia by alkyl groups). The desired optically active fluoroamine can be produced by hydrolyzing the protected optically active fluoroamine under acidic conditions.
• US8217196B2
  申请人：——

  公开号：US8217196B2

  公开（公告）日：2012-07-10
• US8426645B2
  申请人：——

  公开号：US8426645B2

  公开（公告）日：2013-04-23