2-Acetylamino-3-naphthalen-1-yl-propionic acid methyl ester | 24758-27-8

• 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: 2-Acetylamino-3-naphthalen-1-yl-propionic acid methyl ester
• 英文别名: Methyl 2-(acetylamino)-3-(1-naphthyl)propanoate；methyl 2-acetamido-3-naphthalen-1-ylpropanoate
• CAS: 24758-27-8
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: ZDDZHYTXGKVGSJ-UHFFFAOYSA-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：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Acetylamino-3-naphthalen-1-yl-propionic acid methyl ester 、 盐酸 生成 (2S)-2-acetamido-3-(naphthalen-1-yl)propanoic acid
  参考文献：
  名称：

  PORTER, JOHN;DYKERT, JOHN;RIVIER, JEAN, INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 1, 13-21

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2-Acetylamino-3-naphthalen-1-yl-acrylic acid methyl ester 在 甲醇 、 indium 、 (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)quinoxaline 、 溶剂黄146 、 cobalt(II) iodide 作用下， 生成 2-Acetylamino-3-naphthalen-1-yl-propionic acid methyl ester
  参考文献：
  名称：

  钴催化 α-氨基丙烯酸酯的不对称氘化用于 α,β-二氘化 α-氨基酸的立体选择性合成

  摘要：

  使用氘化甲醇作为廉价的氘源，钴催化的对映选择性氘化以优异的对映选择性和几乎完全的氘化提供 α,β-二氘-α-氨基酸。

  DOI：

  10.1002/anie.202301091

文献信息

• Synthesis of α-amino acid derivatives by copper(I)-catalyzed conjugate addition of grignard reagents to methyl 2-acetamidoacrylate
  作者：C. Cardellicchio、V. Fiandanese、G. Marchese、F. Naso、L. Ronzini

  DOI：10.1016/s0040-4039(00)98742-2

  日期：1985.1

  The reactions of Grignard reagents with methyl 2-acetamidoacrylate in the presence of CuI give fair to good yields of α-amino esters; the corresponding α-deutero- or α-methyl-derivatives are obtained upon quenching with D+ or CH3I, respectively.

  在CuI的存在下，格氏试剂与2-乙酰氨基丙烯酸甲酯的反应可以使α-氨基酯的收率达到中等水平。分别用D +或CH 3 I淬灭得到相应的α-氘代或α-甲基衍生物。
• Efficient Access to Alanine Derivatives by 1,4-Additions of Potassium Trifluoro(organo)borates
  作者：Laure Navarre、Sylvain Darses、Jean-Pierre Genet

  DOI：10.1002/ejoc.200300462

  日期：2004.1

  Potassium trifluoro(organo)borates, highly stable and easily prepared organoboron derivatives, were able to react with a great variety of dehydroamino esters. This reaction, catalyzed by rhodium complexes, allowed the formation of alanine derivatives bearing a great variety of amino protecting groups in good to high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  三氟（有机）硼酸钾是一种高度稳定且易于制备的有机硼衍生物，能够与多种脱氢氨基酯反应。该反应由铑配合物催化，能够以良好到高产率形成带有多种氨基保护基团的丙氨酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Synthesis of Functionalised Phenylalanines Using Rhodium Catalysis in Water
  作者：Christopher J. Chapman、Christopher G. Frost

  DOI：10.1002/adsc.200390039

  日期：2003.3

  The efficient synthesis of substituted phenylalanine-type amino acids using a rhodium-catalysed, conjugate addition of arylboronic acids is described. The reactions are run in water and use a low loading (0.5 mol %) of rhodium catalyst.

  描述了使用铑催化的芳基硼酸的共轭加成来有效合成取代的苯丙氨酸型氨基酸。反应在水中进行，并使用低负载量（0.5mol％）的铑催化剂。
• Nonapeptide and decapeptide derivatives of luteinizing hormone releasing hormone, their preparation and pharmaceutical compositions containing them
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0021234A1

  公开（公告）日：1981-01-07

  Nonapeptide and decapeptide analogs of LH-RH of the formula (pyro)Glu-His-V-Ser-W-X-Y-Arg-Pro-Z (I) and the pharmaceutically acceptable salt thereof wherein: V is tryptophyl, phenylalanyl or 3-(1-naphthyl)-L-alanyl; W is tyrosyl, phenylalanyl or 3-(1-pentafluorophenyl)-L-alanyl; X is a D-amino acid residue wherein R is (a) a carbocyclic aryl-containing radical selected from the group consisting of naphthyl, anthryl, fluorenyl, phenanthryl, biphenylyl, benzhydryl and phenyl substituted with three or more straight chain lower alkyl groups; or (b) a saturated carbocyclic radical selected from the group consisting of cyclohexyl substituted with three or more straight chain lower alkyl groups, perhydronaphthyl, perhydrobiphenylyl, perhydro-2,2-diphenylmethyl and adamantyl; Y is leucyl, isoleucyl, nor-leucyl or N-methyl-leucyl; Z is glycinamide or-NH-R1, wherein R' is lower alkyl, cycloalkyl, fluoro lower alkyl or wherein R2 is hydrogen or lower alkyl, are disclosed. These compounds exhibit potent LH-RH agonist properties.

  式中的 LH-RH 的非肽和十肽类似物 (焦)Glu-His-V-Ser-W-X-Y-Arg-Pro-Z (I)及其药学上可接受的盐 其中： V 是色氨酰、苯丙氨酰或 3-(1-萘基)-L-丙氨酰； W 是酪氨酰基、苯丙氨酰基或 3-(1-五氟苯基)-L-丙氨酰； X 是 D-氨基酸残基，其中 R 是 (a) 一个含碳环芳基，选自由萘基、蒽基、芴基、菲基、联苯基、苯hydryl 和被三个或三个以上直链低级烷基取代的苯基组成的组；或 (b) 饱和碳环基，选自由三个或三个以上直链低级烷基取代的环己基、全氢萘 基、全氢联苯基、全氢-2,2-二苯基甲基和金刚烷基组成的组； Y 是亮氨酰、异亮氨酰、去亮氨酰或 N-甲基亮氨酰； Z 是甘氨酰胺或-NH-R1，其中 R' 是低级烷基、环烷基、氟低级烷基或 其中 R2 是氢或低级烷基。这些化合物具有强效的 LH-RH 激动剂特性。
• Nonapeptide and decapeptide analogs of LHRH, useful as LHRH antagonists, methods of making them, and their pharmaceutical uses
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0049628A2

  公开（公告）日：1982-04-14

  Nonapeptide and decapeptide analogs of LHRH which have the formula and the pharmaceutically acceptable salts thereof, wherein: X is a D-alanyl residue wherein one hydrogen on C-3 is replaced by: a) a carbocyclic aryl-containing radical selected from the group consisting of phenyl substituted with three or more straight chain lower alkyl groups, naphthyl, anthryl, fluorenyl, phenanthryl, biphenylyl and benzhydryl; or b) a saturated carbocyclic radical selected from the group consisting of cyclohexyl substituted with three or more straight chain lower alkyl groups, perhydronaphthyl, perhydrobiphenylyl, perhydro-2,2-diphenylmethyl, and adamantyl; or c) a heterocyclic aryl containing radical selected from the group consisting of radicals represented by the following structural formulas: wherein A" and A' are independently selected from the group consisting of hydrogen, lower alkyl, chlorine, and bromine, and G is selected from the group consisting of oxygen, nitrogen, and sulfur; A is an aminoacyl residue selected from the group consisting of L-pyroglutamyl, D-pyroglutamyl, N-acyl-L-prolyl, N-acyl-D-prolyl, N-acyl-D-tryptophanyl, N-acyl-D-phenylalanyl, N-acyl-D-p-halophenylalanyl, and N-acyl-X wherein X is as defined previously; B is an amino acyl residue selected from the group consisting of D-phenylalanyl, D-p-halophenylalanyl, 2,2-diphenylglycyl, and X wherein X is as defined previously; C is an amino acyl residue selected from the group consisting of L-tryptophanyl, D-tryptophanyl, D-phenylalanyl and X wherein X is as defined above; E is glycinamide or -NH-R1, wherein R1 is lower alkyl, cycloalkyl, fluoro lower alkyl or R2 is hydrogen or lower alkyl; are disclosed. These compounds are LHRH antagonists.

  LHRH 的非肽和十肽类似物，其分子式为 及其药学上可接受的盐类，其中 X是D-丙氨酰残基，其中C-3上的一个氢被下列物质取代 a) 一个含碳环芳基，选自由三个或三个以上直链低级烷基取代的苯基、萘基、蒽基、芴基、菲基、联苯基和二苯基组成的组；或 b) 饱和碳环基，选自由三个或三个以上直链低级烷基取代的环己基、过氢萘基、过氢联苯基、过氢-2,2-二苯基甲基和金刚烷基组成的组；或 c) 杂环芳基，选自由下列结构式所代表的基团组成的组： 其中 A "和 A'独立地选自氢、低级烷基、氯和溴组成的组，G 选自氧、氮和硫组成的组； A 是氨基酰基残基，选自由 L-焦谷氨酰、D-焦谷氨酰、N-酰基-L-脯氨酰、N-酰基-D-脯氨酰、N-酰基-D-色氨酰、N-酰基-D-苯丙氨酰、N-酰基-D-对卤苯丙氨酰和 N-酰基-X 所组成的组，其中 X 如前定义； B 是选自 D-苯丙氨酰、D-对卤代苯丙氨酰、2,2-二苯基甘氨酰和 X 所组成的组的氨基酰基残基，其中 X 如前所定义； C 是氨基酰基残基，选自由 L-色氨酰、D-色氨酰、D-苯丙氨酰和 X 所组成的组，其中 X 如前所定义； E 是甘氨酰胺或-NH-R1，其中 R1 是低级烷基、环烷基、氟低级烷基或-NH-R1。 R2 是氢或低级烷基； 这些化合物是 LHRH 拮抗剂。这些化合物是 LHRH 拮抗剂。