(S)-2-(furan-2-carboxamido)-3-phenylpropanoic acid | 354136-02-0

• 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: (S)-2-(furan-2-carboxamido)-3-phenylpropanoic acid
• 英文别名: N-furoyl-L-phenylalanine；(2S)-2-(furan-2-carbonylamino)-3-phenylpropanoic acid
• CAS: 354136-02-0
• 化学式: C₁₄H₁₃NO₄
• mdl: MFCD08483640
• 分子量: 259.262
• InChiKey: FRQFNSRFSXTHII-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(furan-2-carboxamido)-3-phenylpropanoic acid 、 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以60%的产率得到(S)-N-{1-[(1-hydroxy-1,3-dihydro-2,1-benzoxaborol-6-yl)amino]-1-oxo-3-phenylpropan-2-yl}furan-2-carboxamide
  参考文献：
  名称：

  A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

  摘要：

  We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.

  DOI：

  10.1055/s-0033-1339550
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-2-(furan-2-carboxamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

  摘要：

  We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.

  DOI：

  10.1055/s-0033-1339550

文献信息

• PROCESS FOR PREPARING OPTICALLY ACTIVE (S OR R)-ALPHA-AMINO ACID AND OPTICALLY ACTIVE (R OR S)-ALPHA-AMINO ACID ESTER
  申请人：Yamamoto Yasuhito

  公开号：US20090042260A1

  公开（公告）日：2009-02-12

  The present invention discloses a process for preparing an optically active (S or R)-α-amino acid represented by the formula (II): wherein R represents an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aralkyl group, heteroarylalkyl group, aryl group or heteroaryl group, each of which may have a substituent(s), and * represents an asymmetric carbon atom, and an optically active (R or S)-α-amino acid ester represented by the formula (III): wherein R 1 represents an alkyl group which may have a substituent(s), and * represents an asymmetric carbon atom, provided that it has an opposite absolute configuration to that of the compound of the formula (II), which comprises selectively reacting water with one of enantiomers of an α-amino acid ester which is a racemic mixture and represented by the formula (I): wherein R and R 1 have the same meanings as defined above, in the presence of a lipase or a protease in an organic solvent.

  本发明揭示了一种制备光学活性（S或R）-α-氨基酸的方法，其表示为式（II）：其中R表示烷基，烯基，炔基，环烷基，芳基烷基，杂芳基烷基，芳基或杂芳基，每个基团都可以有取代基，而*表示不对称碳原子；以及光学活性（R或S）-α-氨基酸酯，其表示为式（III）：其中R1表示烷基，可以有取代基，而*表示不对称碳原子，前提是它的绝对构型与式（II）的化合物相反；所述方法包括在有机溶剂中，在脂肪酶或蛋白酶的存在下，选择性地将水与由式（I）表示的混合的α-氨基酸酯的对映体之一反应，其中R和R1的含义如上所定义。
• Process for preparing carboxylic acid using surfactant-modified enzyme
  申请人：Miyata Hiroyuki

  公开号：US20090117626A1

  公开（公告）日：2009-05-07

  The present invention relates to a process for preparing a carboxylic acid using a surfactant-modified enzyme which comprises selectively reacting water and a carboxylic acid ester, provided that triglyceride is excluded, in an organic solvent in the presence of a surfactant-modified enzyme.

  本发明涉及一种使用表面活性剂修饰的酶制备羧酸的过程，包括在有机溶剂中，在表面活性剂修饰的酶的存在下，选择性地反应水和羧酸酯，但排除甘油三酯。
• PROCESS FOR PRODUCTION OF CARBOXYLIC ACID USING SURFACTANT-MODIFYING ENZYME
  申请人：Ube Industries, Ltd.

  公开号：EP1887086A1

  公开（公告）日：2008-02-13

  The present invention relates to a process for preparing a carboxylic acid using a surfactant-modified enzyme which comprises selectively reacting water and a carboxylic acid ester, provided that triglyceride is excluded, in an organic solvent in the presence of a surfactant-modified enzyme.

  本发明涉及一种使用表面活性剂改性酶制备羧酸的工艺，该工艺包括在有机溶剂中，在表面活性剂改性酶的存在下，选择性地使水和羧酸酯反应，但不包括甘油三酯。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE (S OR R)-a-AMINO ACID OR OPTICALLY ACTIVE (S OR R)-a -AMINO ACID ESTER
  申请人：Ube Industries, Ltd.

  公开号：EP1942193A1

  公开（公告）日：2008-07-09

  The present invention discloses a process for preparing an optically active (S or R)-α-amino acid represented by the formula (II): wherein R represents an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aralkyl group, heteroarylalkyl group, aryl group or heteroaryl group, each of which may have a substituent(s), and * represents an asymmetric carbon atom, and an optically active (R or S)-α-amino acid ester represented by the formula (III): wherein R1 represents an alkyl group which may have a substituent(s), and * represents an asymmetric carbon atom, provided that it has an opposite absolute configuration to that of the compound of the formula (II), which comprises selectively reacting water with one of enantiomers of an α-amino acid ester which is a racemic mixture and represented by the formula (I): wherein R and R1 have the same meanings as defined above, in the presence of a lipase or a protease in an organic solvent.

  本发明公开了一种制备由式（II）代表的光学活性（S 或 R）-α-氨基酸的工艺： 其中 R 代表烷基、烯基、炔基、环烷基、芳烷基、杂芳烷基、芳基或杂芳基，每个基团可以有一个或多个取代基，* 代表不对称碳原子、 以及由式（III）代表的光学活性（R 或 S）-α-氨基酸酯： 其中 R1 代表一个烷基，该烷基可以有一个或多个取代基，* 代表一个不对称碳原子，但其绝对构型必须与式 (II) 所示化合物的绝对构型相反、 其中包括选择性地使水与α-氨基酸酯的对映体之一反应，α-氨基酸酯是外消旋混合物，由式（I）表示： 其中 R 和 R1 的含义与上述定义相同、 在脂肪酶或蛋白酶存在下，在有机溶剂中进行。
• The Dynamic Kinetic Resolution of Azlactones with Thiol Nucleophiles Catalyzed by Arylated, Deoxygenated Cinchona Alkaloids
  作者：Zaida Rodríguez-Docampo、Cormac Quigley、Sean Tallon、Stephen J. Connon

  DOI：10.1021/jo202662d

  日期：2012.3.2

  A significant improvement of the available organocatalytic methods (in terms of product substrate scope and product enantiomeric excess) for the generation of enantioenriched alpha-amino acid thioesters via the dynamic kinetic resolution of azlactones is reported. C-9 arylated cinchona alkaloid catalysts have been found to be considerably superior to other bifunctional alkaloid catalysts as the promoters of this asymmetric process.