N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-(S)-alanine | 30037-41-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-(S)-alanine
• 英文别名: N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-(S)-phenylalanine；(S)-(-)-N-Benzoyl-3-(4-hydroxy-3-methoxyphenyl)alanin；D,L-N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-alanine；N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-alanine；(2S)-2-benzamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
• CAS: 30037-41-3
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: ODTCNJWUFHCFJB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-(S)-alanine 在 (+)*BF4(-) 氢气 作用下， 生成 (Z)-α-(benzamido)-β-(4-hydroxy-3-methoxyphenyl)acrylic acid
  参考文献：
  名称：

  新型手性双膦配体反式BIS-1,2-(二苯基膦基)环​​丁烷的合成与分离及其铑配合物的不对称氢化

  摘要：

  源自双-1,4-(二苯基膦基)丁烷的1,4-二碳负离子的氧化偶联得到(±)-反式-双-1,2-(二苯基膦基)环​​丁烷。使用通过还原分解的双膦氧化物获得的旋光双膦的铑络合物对脱氢氨基酸进行不对称氢化，以高光学产率提供氢化产物。

  DOI：

  10.1246/cl.1986.613
• 作为产物：
  描述：

  2-(Benzoylamino)-3-(4-hydroxy-3-methoxyphenyl)acrylsaeure 在 <(2R,3R)-2,3-Bis(diphenylphosphino)butan>(ϖ-norbornadien)rhodium(I)-perchlorate 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以98%的产率得到N-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-(S)-alanine
  参考文献：
  名称：

  Koettner, Johann; Greber, Gerd, Chemische Berichte, 1980, vol. 113, # 6, p. 2323 - 2325

  摘要：

  DOI：

文献信息

• Process for the preparation of l-dopa
  申请人：Hoffmann-La Roche Inc.

  公开号：US03969397A1

  公开（公告）日：1976-07-13

  The present invention is directed to preparing L-Dopa, an agent effective in the treatment of Parkinson's Disease, from a D,L-N-benzoyl-3-(4-hydroxy-3-methoxyphenyl) alanine utilizing dehydroabietylamine as a resolving agent and intermediates in this process.

  本发明涉及利用去氢阿比特胺作为分离剂，从D，L-N-苯甲酰-3-(4-羟基-3-甲氧基苯基)丙氨酸制备对帕金森病治疗有效的L-多巴胺，并涉及该过程中的中间体。
• Catalytic asymmetric hydrogenation
  申请人：Monsanto Company

  公开号：US04261919A1

  公开（公告）日：1981-04-14

  Process for the homogeneous catalytic hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids which yields, after hydrogenation, an optically active mixture. The process comprises the hydrogenation of .beta.-substituted-.alpha.-acylamidoacrylic acids in the presence of an optically active coordinated metal complex hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum. This process is a generalized process for any asymmetric hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in which one .alpha.-amino acid enantiomorph is the desired end-product. It is especially useful for the preparation of .alpha.-amino acids found in nature which possess optical activity and which have a hydrogen attached to the asymmetric center. This invention also relates to new optically active coordinated metal complex hydrogenation catalysts.

  .beta.-取代-.alpha.-酰胺基丙烯酸催化氢化的均相催化过程，氢化后产生一种光学活性混合物。该过程包括在光学活性配位金属复合物氢化催化剂的存在下，对.beta.-取代-.alpha.-酰胺基丙烯酸进行氢化，其中金属选自铑、铱、钌、锇、钯和铂的群。该过程是任何不对称氢化.beta.-取代-.alpha.-酰胺基丙烯酸的广义过程，其中一种.alpha.-氨基酸对映异构体是期望的最终产品。它特别适用于制备天然存在、具有光学活性并且在不对称中心附着氢的.alpha.-氨基酸。本发明还涉及新的光学活性配位金属复合物氢化催化剂。
• Methylcyclohexyl-O-anisylphosphine
  申请人：Monsanto Company

  公开号：US04294989A1

  公开（公告）日：1981-10-13

  Process for the homogeneous catalytic hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids which yields, after hydrogenation, an optically active mixture. The process comprises the hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in the presence of an optically active coordinated metal complex hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum. This process is a generalized process for any asymmetric hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in which one .alpha.-amino acid enantiomorph is the desired end-product. It is especially useful for the preparation of .alpha.-amino acids found in nature which possess optical activity and which have a hydrogen attached to the asymmetric center. This invention also relates to new optically active coordinated metal complex hydrogenation catalysts.

  .beta.-取代-.alpha.-酰胺基丙烯酸的均相催化氢化过程，氢化后产生一个光学活性混合物。该过程包括在光学活性配位金属催化剂的存在下，氢化.beta.-取代-.alpha.-酰胺基丙烯酸，其中金属选自铑、铱、钌、锇、钯和铂组成的一组。该过程是任何不对称氢化.beta.-取代-.alpha.-酰胺基丙烯酸的广义过程，其中一个.alpha.-氨基酸对映异构体是期望的最终产物。它特别适用于制备天然存在的具有光学活性并在不对称中心附有氢的.alpha.-氨基酸。本发明还涉及新的光学活性配位金属催化剂。
• Metal coordination complexes containing optically active phosphine or
  申请人：Monsanto Company

  公开号：US04124533A1

  公开（公告）日：1978-11-07

  Process for the homogeneous catalytic hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids which yields, after hydrogenation, an optically active mixture. The process comprises the hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in the presence of an optically active coordinated metal complex hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum. This process is a generalized process for any asymmetric hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in which one .alpha.-amino acid enantiomorph is the desired end-product. It is especially useful for the preparation of .alpha.-amino acids found in nature which possess optical activity and which have a hydrogen attached to the asymmetric center. This invention also relates to new optically active coordinated metal complex hydrogenation catalysts.

  .beta.-取代-.alpha.-酰胺基丙烯酸的均相催化氢化过程，经过氢化后，产生一个旋光性混合物。该过程包括在旋光性配位金属复合催化剂的存在下进行.beta.-取代-.alpha.-酰胺基丙烯酸的氢化，其中金属选自铑、铱、钌、锇、钯和铂的群体。该过程是用于任何不对称氢化的.beta.-取代-.alpha.-酰胺基丙烯酸的广义过程，其中一个.alpha.-氨基酸对映异构体是期望的最终产物。它特别适用于制备在自然界中发现的具有光学活性并且在不对称中心处有氢的.alpha.-氨基酸。本发明还涉及新的旋光性配位金属复合催化剂。
• Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of .alpha.-(acylamino)acrylic acids
  作者：A. Miyashita、A. Yasuda、H. Takaya、K. Toriumi、T. Ito、T. Souchi、R. Noyori

  DOI：10.1021/ja00547a020

  日期：1980.12