CAS: 105746-47-2; Methyl (Trans-4-Isopropylcyclohexane-1-Carbonyl)-D-Phenylalaninate

该化合物是属于氨酸衍生物类的合成化合物.该物质具有苯丙氨基骨,是一种必要的氨基酸,经过添加环己基组和碳酰胺而修改.环氧环上存在的异丙基组会助长其疏水特性,影响其溶解性及其与生物膜的相互作用.甲基酯的功能会增强其亲脂性,有可能影响其生物利用率和药用植物.该化合物可能展示出有趣的生物活动,使其成为医药化学和药物设计的兴趣主体.其结构复杂性允许与生物目标进行各种互动,可以用于治疗用途.与许多合成化合物一样,了解其稳定性,反应性和潜在毒性对于其研发应用至关重要.

英文名称Methyl (Trans-4-Isopropylcyclohexane-1-Carbonyl)-D-Phenylalaninate
中文名称N-[(反式-4-异丙基环己基)羰基]-D-苯丙氨酸甲酯
IUPAC名称methyl ((1r,4R)-4-isopropylcyclohexane-1-carbonyl)-D-phenylalaninate
其它别名Nateglinide Methyl Ester; Nateglinide Impurity; (R)-Methyl 2-((1R,4R)-4-Isopropylcyclohexanecarboxamido)-3-Phenylpropanoate; Nateglinide Impurity 1/nateglinide Methyl Ester/methyl (2S)-3-Phenyl-2-{[(1R,4R)-4-(Propan-2-yl)Cyclohexyl]Formamido}Propanoate; Nateglinide Impurity 8; D-Phenylalanine, N-[[trans-4-(1-Methylethyl)Cyclohexyl]Carbonyl]-, Methyl Ester; Nateglinide Methyl Reference; Methyl (4-Isopropylcyclohexane-1-Carbonyl)-D-Phenylalaninate
CAS编号105746-47-2
MFCD编号:MFCD29079114
分子式:C20H29NO3分子量:331.46
产品CID: 98308
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

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产品信息参考;;;
InChIKey: LUSNEIVFFXOKHW-KZNAEPCWSA-N
InChI=1S/C20H29NO3/c1-14(2)16-9-11-17(12-10-16)19(22)21-18(20(23)24-3)13-15-7-5-4-6-8-15/h4-8,14,16-18H,9-13H2,1-3H3,(H,21,22)/t16-,17-,18-/m1/s1
计算化学: 氢键受体数3.0氢键供体数1.0可旋转键数6.0

MSDS等安全信息

警示词Warning
危险描述H302-H315-H319-H335-
防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338-

上下游产品

trans-4-isopropylcyclohexane-1-carboxylic acid D-phenylalanine methyl ester p-menthan-7-oic acid methyl esterp-menthan-7-oic acid methyl ester D-phenylalanine methyl ester hydr°Chloridenateglinide 19H26NO3(1-)*K(1+)C19H26NO3(1-)*K(1+) 19H26NO3(1-)*Na(1+)C19H26NO3(1-)*Na(1+)

合成工艺路线路线简述

📜D-苯丙氨酸甲酯盐酸盐置于氨,1-羟基苯并三唑体系中,用二氯甲烷,水用作溶剂,化学反应 4.0H,反应生成N-[(反式-4-异丙基环己基)羰基]-D-苯丙氨酸甲酯
参考文献: A Process For The Preparation Of Nateglinide[fr] Procédé De Préparation De Natéglinide
标题: A Process For The Preparation Of Nateglinide[fr] Procédé De Préparation De Natéglinide
摘要:本发明涉及一种制备几乎纯的分子式(i)的那格列奈的方法,该方法基本上不含顺式异构体和l-对映体,并且直接从对映纯的那格列奈b形式的制备,通过在酮溶剂或水或二者混合物中水解(-)-N-(反式-4-异丙基环己基-1-羰基)-D-苯丙氨酸烷基酯制备.

专利信息

专利号:US-6861553-B2
优先权日:2002-07-03
标题:Process for preparing nateglinide and intermediates thereof
发明人：YAHALOMI RONIT; SHAPIRO EVGENY; DOLITZKY BEN-ZION; GOZLAN YIGAEL
权利人:TEVA PHARMA
摘要:Provided is a process for preparation of an intermediate in the synthesis of nateglinide. Trans-4-isopropylcyclohexane acid chloride is formed by reacting 4-isopropylcyclohexanecarboxyl acid with thionyl chloride in the presence of an effective amount of an organic amide.Also provided are processes for preparation of nateglinide by acylation of a suitable salt of D-phenylalanine with trans-4-isopropylcyclohexane acid chloride in both a single and a two phase system, and in water free of a co-solvent.