(R)-N-benzoyl-3-(1-naphthyl)-alanine | 144790-33-0

• 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)-N-benzoyl-3-(1-naphthyl)-alanine
• 英文别名: (2R)-2-benzamido-3-naphthalen-1-ylpropanoic acid
• CAS: 144790-33-0
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: BCKUKGLIXYBCQH-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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)-N-benzoyl-3-(1-naphthyl)-alanine 在 盐酸 作用下， 反应 7.0h， 生成 3-(1-萘基)-L-丙氨酸盐酸盐 、 3-(1-萘基)-D-丙氨酸盐酸盐
  参考文献：
  名称：

  Unusual amino acids III. Asymmetric synthesis of 3-arylalanines

  摘要：

  21 (Z)-alpha-N-benzoylamino-beta-arylacrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-arylalanine derivatives with optical yields in the range of 82-95% ee using the cationic rhodium complex of ''PROPRAPHOS'' as the chiral catalyst No electronical influences of the substituents at the aryl moiety on the enantioselectivity were observed but a sterical one, proved by X-ray crystallographic analysis and computer-aided modellings. Deacylation of the hydrogenated spezies produced the hydrochlorides of the 3-arylalanines attended by a partial racemisation In this case the hydrogenation of urethane type protected dehydroaminoacid derivatives seems to be the alternative.

  DOI：

  10.1016/s0957-4166(00)86017-6
• 作为产物：
  描述：

  (Z)-2-benzamido-3-(naphthalen-1-yl)acrylic acid 在 (+)-(S)-cationic rhodium complex of "PROPHAROS" 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 以100%的产率得到(R)-N-benzoyl-3-(1-naphthyl)-alanine
  参考文献：
  名称：

  Unusual amino acids III. Asymmetric synthesis of 3-arylalanines

  摘要：

  21 (Z)-alpha-N-benzoylamino-beta-arylacrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-arylalanine derivatives with optical yields in the range of 82-95% ee using the cationic rhodium complex of ''PROPRAPHOS'' as the chiral catalyst No electronical influences of the substituents at the aryl moiety on the enantioselectivity were observed but a sterical one, proved by X-ray crystallographic analysis and computer-aided modellings. Deacylation of the hydrogenated spezies produced the hydrochlorides of the 3-arylalanines attended by a partial racemisation In this case the hydrogenation of urethane type protected dehydroaminoacid derivatives seems to be the alternative.

  DOI：

  10.1016/s0957-4166(00)86017-6

文献信息

• Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones
  作者：Joyce Z. Crich、Rosario Brieva、Peer Marquart、Rui Lin Gu、Steffen Flemming、Charles J. Sih

  DOI：10.1021/jo00064a010

  日期：1993.6

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.
• US5219731A
  申请人：——

  公开号：US5219731A

  公开（公告）日：1993-06-15
• Unusual amino acids III. Asymmetric synthesis of 3-arylalanines
  作者：Stefan Taudien、Klaus Schinkowski、Hans-Walter Krause

  DOI：10.1016/s0957-4166(00)86017-6

  日期：1993.1

  21 (Z)-alpha-N-benzoylamino-beta-arylacrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-arylalanine derivatives with optical yields in the range of 82-95% ee using the cationic rhodium complex of ''PROPRAPHOS'' as the chiral catalyst No electronical influences of the substituents at the aryl moiety on the enantioselectivity were observed but a sterical one, proved by X-ray crystallographic analysis and computer-aided modellings. Deacylation of the hydrogenated spezies produced the hydrochlorides of the 3-arylalanines attended by a partial racemisation In this case the hydrogenation of urethane type protected dehydroaminoacid derivatives seems to be the alternative.