(R)-3-benzamido-3-phenylpropanoic acid | 263247-50-3

• 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)-3-benzamido-3-phenylpropanoic acid
• 英文别名: (R)-N-benzoyl-phenylpropanoic acid；(R)-3-benzoylamino-3-phenyl-propionic acid；(R)-3-Benzoylamino-3-phenyl-propionsaeure；N-Benzoyl-beta-phenylalanine；(3R)-3-benzamido-3-phenylpropanoic acid
• CAS: 263247-50-3
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: VRZBLYAGRWDUPY-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-benzamido-3-phenylpropanoic acid 在 盐酸 、 氯化亚砜 、 碘 、 lithium hexamethyldisilazane 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸甲酯
  参考文献：
  名称：

  A Stereoselective Synthesis of (2R,3S)-N-Benzoylphenylisoserine Methyl Ester

  摘要：

  DOI：

  10.1021/jo9714066
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 青霉素(酰胺)酶 、 Eupergit 、 三乙胺 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 14.0h， 生成 (R)-3-benzamido-3-phenylpropanoic acid
  参考文献：
  名称：

  A Stereoselective Synthesis of (2R,3S)-N-Benzoylphenylisoserine Methyl Ester

  摘要：

  DOI：

  10.1021/jo9714066

文献信息

• First Asymmetric Synthesis of a 6-Alkoxy-5,6-dihydro-1,3-oxazine:  A Promising Enantioselective Route to β-Amido Aldehydes
  作者：Patricia Gizecki、Robert Dhal、Loïc Toupet、Gilles Dujardin

  DOI：10.1021/ol991326j

  日期：2000.3.1

  [reaction: see text] The 1,3-oxazine route to enantiopure beta-amido aldehydes was investigated. Heterocycloaddition of the N-acyl imine 1 with (R)-O-vinylpantolactone provided the stable dihydroxazine 4c. High diastereocontrols were observed when using Yb(fod)3-catalyzed or SnCl4-mediated conditions, thus leading after quantitative hydrolysis to (R)-N-benzoyl-3-phenylpropanal with >98% ee.

  [反应：见正文]研究了1,3-恶嗪合成对映体纯的β-酰胺基醛的途径。N-酰基亚胺1与（R）-O-乙烯基泛内酯的杂环加成提供了稳定的二氢恶嗪4c。当使用Yb（fod）3催化或SnCl4介导的条件时，观察到较高的非对映异构控制，因此在定量水解为ee> 98％的（R）-N-苯甲酰基-3-苯基丙醛后会导致高非对映异构。
• One‐Pot Synthesis of Enantioenriched β‐Amino Secondary Amides via an Enantioselective [4+2] Cycloaddition Reaction of Vinyl Azides with <i>N</i> ‐Acyl Imines Catalyzed by a Chiral Brønsted Acid
  作者：Taishi Nakanishi、Jun Kikuchi、Atsushi Kaga、Shunsuke Chiba、Masahiro Terada

  DOI：10.1002/chem.202002049

  日期：2020.7.2

  catalytic enantioselective synthesis of β‐amino secondary amides was achieved using vinyl azides as the enamine‐type nucleophile and chiral N‐Tf phosphoramide as the chiral Brønsted acid catalyst through a five‐step sequential transformation in one pot. The established sequential transformation involves an enantioselective [4+2] cycloaddition reaction of vinyl azides with N‐acyl imines as the key stereo‐determining

  通过在一个罐中进行五步顺序转化，将乙烯基叠氮化物用作烯胺型亲核试剂，将手性N- Tf磷酰胺用作手性布朗斯台德酸催化剂，实现了β-氨基仲酰胺的催化对映选择性合成。建立的顺序转化涉及叠氮化物与N-酰基亚胺的对映选择性[4 + 2]环加成反应，这是关键的立体确定步骤，可通过手性N来有效地加速‐Tf磷酰胺催化剂在大多数情况下都具有高度对映选择性。通过环加成产物的开环和随后涉及施密特型1,2-芳基迁移的骨架重排以及随后的腈离子的再环化，也进一步引发了亚氨基重氮离子中间体的生成。在同一罐中对循环产物进行最终的酸水解，通过在仲酰胺的α位形成C-C键，产生了对映体富集的β-氨基酰胺。
• Processes For Preparing Optically Active (S Or R-)-Beta-Amino Acid And Optically Active (R Or S)-Beta-Amino Acid Ester, And Beta-Amino Acid 2-Alkoxyethyl Ester And Optically Active (S Or R)-Beta Amino Acid 2-Alkoxyethyl Ester
  申请人：Konegawa Tadayoshi

  公开号：US20080038785A1

  公开（公告）日：2008-02-14

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

  本发明涉及一种制备光学活性的(S或R)-β-氨基酸的过程，其表示为公式(II)：其中R表示一种可以具有取代基的烷基、烯基、炔基、环烷基、芳基、芳基烷基或杂环芳基，*表示一个不对称碳原子，以及一种光学活性的(R或S)-β-氨基酸酯，其表示为公式(III)：其中R具有上述定义的相同含义，R1表示一种可以具有取代基的烷基，*表示一个不对称碳原子，前提是它具有与公式(II)化合物相反的绝对构型，其包括在有机溶剂中，在水和公式(I)表示的β-氨基酸酯的对映体之一中选择性水解，其中R和R1具有上述定义的相同含义，它是一个外消旋混合物，存在水解酶。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE (S)- OR (R)- BETA-AMINO ACIDS AND OPTICALLY ACTIVE (R)- OR (S)-BETA -AMINO ACID ESTERS, 2-ALKOXYETHYL ESTERS OF -AMINO ACIDS, AND OPTICALLY ACITVE (S)- OR (R)-2-ALKOXYETHYL ESTERS OF -AMINO ACIDS
  申请人：Ube Industries, Ltd.

  公开号：EP1840218A1

  公开（公告）日：2007-10-03

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

  本发明涉及一种制备由式（II）代表的光学活性（S 或 R）-β-氨基酸的工艺： 其中 R 代表烷基、烯基、炔基、环烷基、芳烷基、芳基或杂芳基，每个基团都可带有取代基， * 代表不对称碳原子、 以及由式（III）代表的光学活性（R 或 S）-β-氨基酸酯： 其中 R 的含义与上文所定义的相同，R1 代表烷基，可带有取代基，* 代表不对称碳原子，但其绝对构型与式 (II) 化合物的绝对构型相反、 其中包括选择性地水解水和式（I）所代表的 β-氨基酸酯的对映体之一： 其中 R 和 R1 的含义与上述定义相同、 其中 R 和 R1 的含义与上文所定义的相同。
• MONOFUNCTIONAL BRANCHED POLYETHYLENEGLYCOL AND BIO-RELATED SUBSTANCE MODIFIED BY SAME
  申请人：Xiamen Sinopeg Biotech Co., Ltd.

  公开号：EP2947111A1

  公开（公告）日：2015-11-25

  Disclosed are a monofunctional branched polyethyleneglycol and a bio-related substance modified by same. The general formula of the monofunctional branched polyethyleneglycol is shown in Formula (1), and the general formula of the bio-related substance modified by the polyethyleneglycol is shown in Formula (2), wherein X1 and X2 are respectively an alkyl group with 1 to 20 carbon atoms; n1 and n2 are respectively an integer ranging from 1 to 1000; n3 is an integer ranging from 11 to 1000; L1 and L2 are respectively a linking group stably existing in illumination, enzyme, acidic, or alkaline conditions; p is 0 or 1, and q is 0 or 1; R1 is a hydrogen atom or an alkyl group with 1 to 20 carbon atoms; D is the bio-related substance; and Z is a linking group, through which a functional group capable of reacting with the bio-related substance is linked to a symmetric axis polyethyleneglycol main chain. The bio-related substance modified by the polyethyleneglycol maintains good biological activity, and has good solubility and long metabolic half-life in an organism.

  本发明公开了一种单官能团支链聚乙二醇和由其改性的生物相关物质。单官能团支链聚乙二醇的通式如式（1）所示，由该聚乙二醇改性的生物相关物质的通式如式（2）所示，其中 X1 和 X2 分别为具有 1 至 20 个碳原子的烷基；n1 和 n2 分别为 1 至 1000 的整数；n3 为 11 至 1000 的整数；L1和L2分别为在光照、酶、酸性或碱性条件下稳定存在的连接基团；p为0或1，q为0或1；R1为氢原子或具有1至20个碳原子的烷基；D为生物相关物质；Z为连接基团，通过该连接基团，能够与生物相关物质反应的官能团被连接到对称轴聚乙二醇主链上。经聚乙二醇改性的生物相关物质可保持良好的生物活性，在生物体内具有良好的溶解性和较长的代谢半衰期。