N-methyl-3-amino-3-phenylpropionamide | 180264-40-8

• 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: N-methyl-3-amino-3-phenylpropionamide
• 英文别名: 3-amino-N-methyl-3-phenylpropanamide
• CAS: 180264-40-8
• 化学式: C₁₀H₁₄N₂O
• mdl: MFCD09945160
• 分子量: 178.234
• InChiKey: RWXOHDDTUTYSHC-UHFFFAOYSA-N

物化性质

• 沸点：
  384.4±35.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-3-amino-3-phenylpropionamide 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 rac-trans-1-benzoyl-2,6-diphenyl-3-methylperhydropyrimidin-4-one
  参考文献：
  名称：

  X-ray Crystallographic Study of Substituted Perhydropyrimidinones. Extreme Changes in Ring Conformation

  摘要：

  X-ray crystal structures of 20 differently substituted perhydropyrimidin-4-ones are presented. Analysis of these data reveal a remarkable conformational sensitivity of a six-membered ring to substitution. Thus half-chair; envelope, boat, twist-boat, and intermediate conformations are found for the six-membered heterocycle, providing evidence for a relatively flat conformational energy surface in this ring, interpretation of the preferred conformations is advanced in terms of steric interactions among substituents and, in some cases, as the result of particular conformational (A(1,3) strain, anomeric) effects.

  DOI：

  10.1021/jo991297q
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 乙酰氯 作用下， 以 水 为溶剂， 反应 2.5h， 生成 N-methyl-3-amino-3-phenylpropionamide
  参考文献：
  名称：

  通过碰撞诱导解离的异构体分化：质子化的α-，β2-和β3-苯丙氨酸及其衍生物

  摘要：

  电喷雾电离（ESI），多级和高分辨率质谱实验的组合被用于检查三种同分异构的苯丙氨酸衍生物，α苯丙氨酸的气相碎裂反应，β 2 -苯丙氨酸和β 3 -苯丙氨酸。在碰撞诱导解离（CID）条件下，每个质子化的苯丙氨酸异构体的碎片均不同，从而可以区分。例如，质子化的β 3个经由NH的损失-苯丙氨酸片段几乎完全3中，只有β 2通过H的损失-苯丙氨酸2 O，而α-和β 2 -苯丙氨酸片段主要通过H的结合损失2O + CO。进行了密度泛函理论（DFT）计算，以检查每种质子化苯丙氨酸异构体的NH 3损失与H 2 O和CO的合并损失之间的竞争。研究了三种潜在的NH 3损失途径：（i）芳基辅助的邻近基团；（ii）1，2氢化物迁移；（iii）相邻基团被羧基所参​​与。最后，我们已经表明，异构体分化，也可以当CID上的α-质子化甲酯和甲基酰胺衍生物进行的，β 2 -和β 3 -phenylalanines。版权所有©2010

  DOI：

  10.1002/rcm.4576

文献信息

• [EN] RACEMIC PREPARATION METHOD FOR CHIRAL β-AMINO ACID AND DERIVATIVE THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION RACÉMIQUE POUR UN ACIDE β-AMINÉ CHIRAL ET UN DÉRIVÉ DE CE DERNIER<br/>[ZH] 一种手性β-氨基酸及其衍生物的消旋制备方法
  申请人：ZHEJIANG JIUZHOU PHARM CO LTD

  公开号：WO2021017645A1

  公开（公告）日：2021-02-04

  本发明属于医药合成领域，涉及制备手性β-氨基酸及其衍生物的消旋制备方法，特别是涉及一种西格列汀中间体的消旋方法。(I), (II) 其中，R1为氢、烷基或芳基；R2为氢、烷基或芳基；R3为氢、烷基、芳基或酰基；R4为烷基、芳基、OR'、SR'、NHR'或NR'R"。其中R'，R"为氢、烷基或芳基。
• SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES
  申请人：BRITISH BIOTECH PHARMACEUTICALS LIMITED

  公开号：EP0861226B1

  公开（公告）日：2000-02-23
• US5986132A
  申请人：——

  公开号：US5986132A

  公开（公告）日：1999-11-16
• [EN] SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES<br/>[FR] SYNTHESE DE DERIVES D'ACIDE CARBOXYLIQUE
  申请人：BRITISH BIOTECH PHARMACEUTICALS LIMITED

  公开号：WO1997019050A1

  公开（公告）日：1997-05-29

  (EN) Compounds of formula (I) wherein R1, R2, R3, R4, X are as defined in the specification and are prepared by elimination of one of the groups X1 and X2 from a compound of formula (II) wherein X1 and X2 each independently represent a carboxylic acid group or salt thereof, or a protected carboxylic acid group, the non-eliminated group X1 or X2 corresponding to the group X in the desired compound of formula (I).(FR) Composés de formule (I) dans laquelle R1, R2, R3, R4, X sont tels que définis dans la description du brevet. Pour préparer ces composés on élimine un des groupes X1 et X2 d'un composé de formule (II) dans laquelle X1 et X2 représentent chacun indépendamment un groupe acide carboxylique ou un sel de ce dernier, ou bien un groupe acide carboxylique protégé, le groupe X1 ou X2 non éliminé correspondant au groupe X dans le composé désiré de formule (I).
• [EN] AMINO ACID DERIVATIVES AS INHIBITORS OF MAMMALIAN SODIUM CHANNELS<br/>[FR] DERIVES D'ACIDES AMINES EN TANT QU'INHIBITEURS DES CANAUX SODIQUES DE MAMMIFERES
  申请人：IONIX PHARMACEUTICALS LTD

  公开号：WO2004087125A1

  公开（公告）日：2004-10-14

  Use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for use in the treatment or prevention of a condition selected from chronic and acute pain, tinnitus, bowel disorders, bladder dysfunctions and demyelinating diseases, Formula (I) wherein: - R1 is Cl-C6 alkyl, C6-C10 aryl, a 5- to 10- membered heteroaryl group, a 5- to 10- membered heterocyclyl group or a C3-C6 carbocyclyl group; each R2 is the same or different and represents Cl-C6 alkyl, halogen, Cl-C6 alkoxy, Cl-C6 alkythio, hydroxy, nitro, cyano, amino, (Cl-C6 alkyl)amino or di-( Cl-C6 alkyl)amino; - R3 represents hydrogen, Cl-C6 alkyl, or together with R4 represents a C2-C4 alkylene group; - R4 is hydrogen, Cl-C6 alkyl, C6-C10 aryl, C3-C6 carbocyclyl, a 5- to 10­membered heteroaryl group, a 5- to 10- membered heterocyclyl group, -( Cl-C6 alkyl)-(C6-C10 aryl), -(C1-C6 alkyl)-(C3-C6 carbocyclyl), -(C1-C6 alkyl)-(5-to 10- membered heteroaryl), - ( Cl-C6 alkyl)-(5- to 10- membered heterocyclyl) or, together with R3 represents a C2-C4 alkylene group; - R5 and R6 are the same or different and each represent hydrogen or a Cl-C6 alkyl group; - n is 0,1, 2, 3 or 4; X1 represents a direct bond or a methylene group; and X2 represents a -CH2-, -CO-, -SO- or -S(O)2- group, wherein: the alkyl and alkylene groups and moieties in the substituents R1 to R6 and X, are unsubstituted or are substituted by 1, 2 or 3 substituents which are the same or different and are selected from hydroxy, amino, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino and di(C1-C4 alkyl)amino substituents; and the aryl, heteroaryl, heterocyclyl and carbocyclyl groups and moieties in the substituents R1 and R4 are unsubstituted or are substituted by 1, 2 or 3 substituents which are the same or different and are selected from halogen, Cl-C6 alkyl, Cl-C6 alkoxy, Cl-C6 alkylthio, hydroxy, amino, Cl-C6 alkylamino, di-( Cl-C6 alkyl)amino, Cl-C6 haloalkyl, Cl-C6 haloalkoxy and Cl-C6 haloalkylthio substituents. provided that, when n is 1, 2, 3 or 4, R4 is other than hydrogen and when n is 0, X2 is -CH2- and R1 is an aryl or heteroaryl group, then either: (a) R, is a phenyl group which carries at least one -SCF3 substituent or is a thienyl group which carries at least one chloro substituent; (d) R1 is a phenyl group which carries at least one -CF3 substituent or at least two halogen substituents; or (e) R4 is benzyl or hydroxybenzyl and R1 is a phenyl group which carries a fluorine or -OCH3 substituent.