diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate | 5440-57-3

• 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: diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate
• 英文别名: diethyl (1-methylnaphthyl)acetamidomalonate；acetylamino-[1]naphthylmethyl-malonic acid diethyl ester；Acetamino-(naphthyl-(1)-methyl)-malonsaeure-diaethylester；Acetylamino-[1]naphthylmethyl-malonsaeure-diaethylester；DIETHYL 2-[(1-NAPHTHYL)METHYL]-2-ACETAMIDOMALONATE；Acetamino--malonsaeure-diethylester；Diethyl acetamido[(naphthalen-1-yl)methyl]propanedioate；diethyl 2-acetamido-2-(naphthalen-1-ylmethyl)propanedioate
• CAS: 5440-57-3
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: LGRLDHYLVHVRRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.17h， 生成 3-(1-萘基)-L-丙氨酸
  参考文献：
  名称：

  Synthesis and biological activities of cholecystokinin analogues substituted in position 30 by 3-(1-naphthyl)-l-alanine [Nal(1)] or 3-(2-naphthyl)-l-alanine [Nal(2)]

  摘要：

  Acetyl derivatives of ethyl esters of 3-(1-naphthyl)-D,L-alanine and 3-(2-naphthyl)-D,L-alanine were synthesized through a malonic condensation. Resolution of these derivatives by subtilisin Carlsberg followed by acid hydrolysis afforded the 2 optical isomers of 3-(1-naphthyl)-alanine [Nal(1)] and 3-(2-naphthyl)-alanine [Nal(2)]. The L enantiomers of these amino acids were incorporated into the sequence of cholecystokinin in place of the tryptophan in position 30. The cholecystokinin analogues thus obtained behaved as full agonists, with reduced potencies on rat pancreatic acini and on guinea pig brain membranes, by about one order of magnitude for the Nal(2) derivative and by 2 orders of magnitude for the Nal(1) derivative, as compared to the potent parent compound Boc-Tyr(SO3H)-Nle-Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/0223-5234(91)90056-s
• 作为产物：
  描述：

  (氯甲基)萘 、 乙酰氨基丙二酸二乙酯 在 sodium 作用下， 以 乙醇 为溶剂， 以79%的产率得到diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate
  参考文献：
  名称：

  Tricyclic amides

  摘要：

  该发明涉及一种选择自以下公式(I)的化合物：##STR1## 其中R.sub.7，R.sub.8，Y，n和A如描述中定义，并含有相同化合物的药物产品，适用于治疗褪黑激素系统障碍。

  公开号：

  US05712312A1

文献信息

• Tricyclic amides
  申请人：Adir et Compagnie

  公开号：US05712312A1

  公开（公告）日：1998-01-27

  The invention relates to a compound selected from these of formula (I): ##STR1## in which R.sub.7, R.sub.8, Y, n and A are as defined in the description, and medicinal product containing the same useful for treating a disorder of the melatoninergic system.

  该发明涉及一种选择自以下公式(I)的化合物：##STR1## 其中R.sub.7，R.sub.8，Y，n和A如描述中定义，并含有相同化合物的药物产品，适用于治疗褪黑激素系统障碍。
• Palladium-Catalyzed Benzylation of Active Methine Compounds without Additional Base:  Remarkable Effect of 1,5-Cyclooctadiene
  作者：Ryoichi Kuwano、Yutaka Kondo

  DOI：10.1021/ol048540e

  日期：2004.9.1

  The palladium complex prepared from DPPF and Cp(eta(3)-C3H5)Pd is an effective catalyst for the alkylation of active methine compounds with benzylic carbonates under neutral conditions. The addition of 1,5-cyclooctadiene brought about remarkable improvement in the lifetime of the palladium catalyst, which led to high yields of the desired benzylation products.
• Substituted Acetamidomalonic Esters and dl-2-Acetamido Acids as Antitumor Agents
  作者：John Andrako、J. Doyle Smith、Walter H. Hartung

  DOI：10.1002/jps.2600500413

  日期：1961.4
• �ber die Synthese von zwei mit Tryptophan isosteren Verbindungen: ?-[Cumaronyl-(3)]-alanin und ?-[Naphtyl-(1)]-alanin
  作者：H. Erlenmeyer、W. Grubenmann

  DOI：10.1002/hlca.19470300138

  日期：1947.2.1
• PORTER, JOHN;DYKERT, JOHN;RIVIER, JEAN, INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 1, 13-21
  作者：PORTER, JOHN、DYKERT, JOHN、RIVIER, JEAN

  DOI：——

  日期：——