2-(3-methoxyphenyl)-1,3-diaminopropane | 78533-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenyl)-1,3-diaminopropane
• 英文别名: 2-(3-methoxyphenyl)propane-1,3-diamine；2-(3-methoxyphenyl)-1,3-propanediamine
• CAS: 78533-92-3
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: ZZJUKSRKKDZJED-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C
• 沸点：
  320.9±32.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-二羧甲基-2-甲基-2-硫代异脲 、 2-(3-methoxyphenyl)-1,3-diaminopropane 在 甲醇 作用下， 以 甲醇 为溶剂， 以to give 2.62 g of 2-methoxycarbonylamino-5-(3-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine, mp 218°-221°的产率得到2-methoxycarbonylamino-5-(3-methoxyphenyl)-1,4,5,6-tetrahydropyrimidine
  参考文献：
  名称：

  4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydro-pyrimidine derivatives

  摘要：

  特定的1,4,5,6-四氢嘧啶化合物，在2位被氨基，酰胺基或氨基甲酸酯取代，在5位或4位（当1位没有烷基时）被取代的苯基（可选取代）或当苯基在5位时，在1位可选取代为较低的烷基。这些化合物可用作中枢神经系统药物和降压药。

  公开号：

  US04322421A1
• 作为产物：
  描述：

  3-(3-methoxyphenyl)glutaramide 在 sodium hydroxide 、 溴 作用下， 以42%的产率得到2-(3-methoxyphenyl)-1,3-diaminopropane
  参考文献：
  名称：

  Synthesis and antidepressant profiles of phenyl-substituted 2-amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydropyrimidines

  摘要：

  A series of 4(6)- and 5-phenyl-substituted 2-amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydropyrimidines were prepared and evaluated for central nervous system (CNS) effects in animal models. Several 5-phenyl-substituted compounds possessed potent antidepressant activity and all compounds in this series were devoid of significant activity in any of the other CNS (anticonvulsant, muscle relaxant, and depressant) assays. The most active compound in the in vivo screen for antidepressant activity (reversal of reserpine-induced hypothermia), 2-[(methoxycarbonyl)amino]-5-phenyl-1,4,5,6-tetrahydropyrimidine was considerably more potent than tricyclic antidepressant (TCA) standards. The 2-amino parent compound on the other hand was greater than 100-fold as effective as TCA's in in vitro inhibition of norepinephrine and dopamine uptake.

  DOI：

  10.1021/jm00383a002

文献信息

• Enzymatic Desymmetrization of Prochiral 2-Substituted-1,3-Diamines: Preparation of Valuable Nitrogenated Compounds
  作者：Nicolás Ríos-Lombardía、Eduardo Busto、Eduardo García-Urdiales、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/jo8025912

  日期：2009.3.20

  A wide range of prochiral 1,3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates

  首先有效地合成了多种前手性的1,3-二胺，然后使用洋葱假单胞菌的脂肪酶作为催化剂，碳酸二烯丙酯作为烷氧基羰基化剂进行了脱对称。在所有情况下，都回收了R-构型的氨基氨基甲酸酯。N-烯丙氧羰基部分的最终选择性裂解是在温和的反应条件下进行的，这表明该化学酶促途径具有很高的通用性和潜力，可作为相关旋光性氮化衍生物合成中的中间体来源。
• 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04261995A1

  公开（公告）日：1981-04-14

  Certain 1,4,5,6-tetrahydropyrimidine compounds which are substituted with an amino, amido or carbamate at the 2-position, with an optionally substituted phenyl at the 5-position or at the 4-position when there is no alkyl at the 1-position and optionally a lower alkyl at the 1-position when the phenyl is at the 5-position are useful as CNS agents and as antihypertensives.

  某些在2位被氨基、酰胺或氨基甲酸酯取代的1,4,5,6-四氢嘧啶化合物，在5位或4位（当1位没有烷基时）可选地用取代的苯基进行取代，在5位有苯基时，1位可选地用较低的烷基进行取代，这些化合物可用作中枢神经系统药物和降压药。
• 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydro-pyrimidine derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04322421A1

  公开（公告）日：1982-03-30

  Certain 1,4,5,6-tetrahydropyrimidine compounds which are substituted with an amino, amido or carbamate at the 2-position, with an optionally substituted phenyl at the 5-position or at the 4-position when there is no alkyl at the 1-position and optionally a lower alkyl at the 1-position when the phenyl is at the 5-position are useful as CNS agents and as antihypertensives.

  特定的1,4,5,6-四氢嘧啶化合物，在2位被氨基，酰胺基或氨基甲酸酯取代，在5位或4位（当1位没有烷基时）被取代的苯基（可选取代）或当苯基在5位时，在1位可选取代为较低的烷基。这些化合物可用作中枢神经系统药物和降压药。
• 4-Phenyl and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives, pharmaceutical compositions containing said derivatives, and process for preparing said derivatives
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0024776A1

  公开（公告）日：1981-03-11

  Compounds represented by the formula wherein A is H, where R is alkyl of one through six carbon atoms; X is hydrogen, fluoro, chloro, bromo, iodo, hydroxy, alkoxy of one through four carbon atoms, benzyloxy, alkyl of one through four carbon atoms, alkylthio of one through four carbon atoms, alkylsulfinyl of one through four carbon atoms, alkylsulfonyl of one through four carbon atoms or trifluoromethyl; and Y is hydrogen or is the same as X; and R' is hydrogen or alkyl of one through four carbon atoms; the phenyl substituent carrying the X and Y is at the 4- or 5-position of the tetrahydropyrimidine ring when R' is hydrogen or is at the 5-position when R' is alkyl; and the pharmaceutically acceptable salts thereof. These compounds are pharmaceutically useful for treating depression, anxiety, convulsions, centrally-induced' skeletal muscle spasm and spasticity.

  由式表示的化合物 式中 A 是 H 其中 R 是一至六个碳原子的烷基； X 是氢、氟、氯、溴、碘、羟基、一至四个碳原子的烷氧基、苄氧基、一至四个碳原子的烷基、一至四个碳原子的烷硫基、一至四个碳原子的烷基亚磺酰基、一至四个碳原子的烷基磺酰基或三氟甲基；和 Y 是氢或与 X 相同；以及 R'为氢或一至四个碳原子的烷基；当 R' 为氢时，携带 X 和 Y 的苯基取代基位于四氢嘧啶环的 4 位或 5 位，当 R' 为烷基时，位于 5 位；及其药学上可接受的盐类。 这些化合物可用于治疗抑郁症、焦虑症、抽搐、中枢诱发的骨骼肌痉挛和痉挛。
• WEINHARDT, K.;WALLACH, M. B.;MARX, M., J. MED. CHEM., 1985, 28, N 6, 694-698
  作者：WEINHARDT, K.、WALLACH, M. B.、MARX, M.

  DOI：——

  日期：——