diethyl (dipropylamino)malonate | 82697-03-8

• 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: diethyl (dipropylamino)malonate
• 英文别名: diethyl di-n-propylaminomalonate；Diethyl (dipropylamino)propanedioate；diethyl 2-(dipropylamino)propanedioate
• CAS: 82697-03-8
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: UVXPPRDKOGYPOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (dipropylamino)malonate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 仲丁基锂 、 sodium ethanolate 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 50.25h， 生成 6-(dipropylamino)-6,7-dihydro-1H,3H,5H-pyrido<1,2,3-ij>-3,1-benzoxazin-3-one
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013
• 作为产物：
  描述：

  二正丙胺 、 溴代丙二酸二乙酯 在 二丙胺氢溴酸盐 、 四氢呋喃 、 乙酸乙酯 、 sodium hydroxide 、 水 、 正己烷 、 ethyl acetate n-hexane 、 diethyl (dipropylamino)malonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以to give diethyl (dipropylamino)malonate as an oil in 80-90% yield的产率得到diethyl (dipropylamino)malonate
  参考文献：
  名称：

  Heterocyclic amines having central nervous system activity

  摘要：

  三环氮含化合物，具有下列结构式的中枢神经系统活性：##STR1##及其药学上可接受的盐，其中R.sub.1、R.sub.2和R.sub.3独立地为氢、C.sub.1-6烷基、烯基或炔基、C.sub.3-10环烷基，或R.sub.1和R.sub.2结合形成可含有额外杂原子的C.sub.3-7环胺；X为氢、C.sub.1-6烷基卤素、羟基、烷氧基、氰基、羧酰胺、羧基或羧基烷氧基；A为SO.sub.2、N、CH、CH.sub.2、CHCH.sub.3、C.dbd.O、C.dbd.S、C-SCH.sub.3、C.dbd.NH、C-NH.sub.2、C-NHCH.sub.3、C--NHCOOCH.sub.3或C--NHCN。B为CH.sub.2、CH、C.dbd.O、N、NH或N--CH.sub.3；n为0或1；D为CH、CH.sub.2、C.dbd.O、O、N、NH或N--CH.sub.3。这些新化合物适用于治疗精神分裂症、帕金森病、焦虑症、抑郁症，或作为降低动物或人体内血压的化合物。

  公开号：

  US05273975A1
• 作为试剂：
  描述：

  二正丙胺 、 溴代丙二酸二乙酯 在 二丙胺氢溴酸盐 、 四氢呋喃 、 乙酸乙酯 、 sodium hydroxide 、 水 、 正己烷 、 ethyl acetate n-hexane 、 diethyl (dipropylamino)malonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以to give diethyl (dipropylamino)malonate as an oil in 80-90% yield的产率得到diethyl (dipropylamino)malonate
  参考文献：
  名称：

  Heterocyclic amines having central nervous system activity

  摘要：

  含有三环氮化合物，具有以下结构式的中枢神经系统活性：##STR1##和其药学上可接受的盐，其中R.sub.1，R.sub.2和R.sub.3独立地是氢，C.sub.1-6烷基，烯基或炔基，C.sub.3-10环烷基，或R.sub.1和R.sub.2连接形成可以包含额外杂原子的C.sub.3-7环胺；X是氢，C.sub.1-6烷基，卤素，羟基，烷氧基，氰基，羧酰胺，羧基或羧基烷氧基；A是SO.sub.2，N，CH，CH.sub.2，CHCH.sub.3，C=O，C=S，C-SCH.sub.3，C=NH，C-NH.sub.2，C-NHCH.sub.3，CNHCOOCH.sub.3或C-NHCN。B是CH.sub.2，CH，C=O，N，NH或N-CH.sub.3；n为0或1；D是CH，CH.sub.2，C=O，0，N，NH或N-CH.sub.3。这些新化合物适用于治疗精神分裂症、帕金森病、焦虑症、抑郁症或作为降低动物或人体内血压的化合物。

  公开号：

  US05436240A1

文献信息

• Thiazolo[3,2-a]pyrimidines, derivatives thereof, processes for
  申请人：Teijin Limited

  公开号：US04421914A1

  公开（公告）日：1983-12-20

  A compound selected from thiazolo[3,2-a]pyrimidines or their enolate derivatives represented by the following general formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different, and each represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted cycloaliphatic group having 3 to 8 carbon atoms, a substituted or unsubstituted phenylalkyl group or a substituted or unsubstituted acyl group having 2 to 7 carbon atoms, provided that R.sup.1 and R.sup.2 are not simultaneously hydrogen atoms or substituted or unsubstituted acyl groups having 2 to 7 carbon atoms; and R.sup.1 and R.sup.2, when taken together, may form, with the nitrogen atom to which they are bonded, a 5- or 6-membered ring which may further contain one or more hetero atoms; and acid addition salts of these compounds. The thiazolo[3,2-a]pyrimidines may be prepared by a process comprising (a) reacting a malonic acid derivative of the following general formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined with regard to formula (I), and R.sup.4 and R.sup.5 are identical or different and each represents an alkyl group having 1 to 6 carbon atoms, with 2-aminothiazoline under heat, if desired in the presence of an inert organic solvent, to induce cyclocondensation, or (b) performing said condensation reaction in the presence of an alkali metal alkoxide, if desired in the presence of an inert organic solvent, and neutralizing the resulting enolate with an acid; and if desired, reacting the reaction product of (a) or (b) with an acid. The present invention provides also several processes for preparing enolate derivatives thereof. The thiazolo[3,2-a]pyrimidines, their enolate derivatives and acid addition compounds thereof are useful for regulating the immune function of a warm-blooded animal.

  本发明涉及一种从噻唑并[3,2-a]嘧啶或其烯醇衍生物中选择的化合物，其通式如下：##STR1## 其中R1和R2相同或不同，每个代表氢原子，具有1至10个碳原子的烷基，具有3至10个碳原子的烯基，取代或未取代的苯基，具有3至8个碳原子的取代或未取代的环脂肪基，取代或未取代的苯基烷基或具有2至7个碳原子的取代或未取代的酰基，但要求R1和R2不同时为氢原子或具有2至7个碳原子的取代或未取代的酰基；当R1和R2结合时，它们可以与它们连接的氮原子形成一个5或6成员环，该环可以进一步包含一个或多个杂原子；以及这些化合物的酸盐。噻唑并[3,2-a]嘧啶可以通过以下过程制备：（a）将以下通式的丙二酸衍生物与2-氨基噻唑烷在热下反应，如果需要，在惰性有机溶剂的存在下诱导环缩合，其中R1和R2如式（I）所定义，R4和R5相同或不同，每个代表具有1至6个碳原子的烷基；或者（b）在碱金属醇的存在下进行该缩合反应，如果需要，在惰性有机溶剂的存在下，并用酸中和所得的烯醇；如果需要，反应（a）或（b）的反应产物可以与酸反应。本发明还提供了几种制备其烯醇衍生物的方法。噻唑并[3,2-a]嘧啶，其烯醇衍生物和酸加成化合物对于调节温血动物的免疫功能有用。
• Novel thiazolo(3,2-a)pyrimidines, derivatives thereof, processes for production thereof, and pharmaceutical use thereof
  申请人：TEIJIN LIMITED

  公开号：EP0049902A2

  公开（公告）日：1982-04-21

  A compound selected from thiazolo(3,2-a)pyrimidines or their enolate derivatives represented by the following general formula wherein R1 and R2 are identical or different, and each represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted cycloaliphatic group having 3 to 8 carbon atoms, a substituted or unsubstituted phenylalkyl group or a substituted or unsubstituted acyl group having 2 to 7 carbon atoms, provided that R and R2 are not simultaneously hydrogen atoms or substituted or unsubstituted acyl groups having 2 to 7 carbon atoms; and R and R2, when taken together, may form, with the nitrogen atom to which they are bonded, a 5- or 6-membered ring which may further contain one or more hetero atoms; and acid addition salts of these compounds. The thiazolo(3,2-a)pyrimidines may be prepared by a process comprising (a) reacting a malonic acid derivative of the following general formula wherein R' and R2 are as defined with regard to formula (I), and R4 and R5 are identical or different and each represents an alkyl group having 1 to 6 carbon atoms, with 2-aminothiazoline under heat, if desired in the presence of an inert organic solvent, to induce cyclocondensation, or (b) performing said condensation reaction in the presence of an alkali metal alkoxide, if desired in the presence of an inert organic solvent, and neutralizing the resulting enolate with an acid: and if desired, reacting the reaction product of (a) or (b) with an acid. The present invention provides also several processes for preparing enolate derivatives thereof. The thiazolo(3,2-a)pyrimidines, their enolate derivatives and acid addition compounds thereof are useful for regulating the immune function of a warm-blooded animal.

  选自以下通式所代表的噻唑并(3,2-a)嘧啶或其烯内酯衍生物的化合物 其中 R1 和 R2 相同或不同，且各自代表氢原子、具有 1 至 10 个碳原子的烷基、具有 3 至 10 个碳原子的烯基、取代或未取代的苯基、具有 3 至 8 个碳原子的取代或未取代的环脂族基团、取代或未取代的苯基烷基或具有 2 至 7 个碳原子的取代或未取代的酰基，但 R 和 R2 不能同时为氢原子或具有 2 至 7 个碳原子的取代或未取代的酰基；当 R 和 R2 结合在一起时，可与它们所结合的氮原子形成一个 5 或 6 元环，该环可进一步含有一个或多个杂原子；以及这些化合物的酸加成盐。 噻唑并(3,2-a)嘧啶可通过以下工艺制备：(a) 使以下通式的丙二酸衍生物发生反应 其中 R' 和 R2 如式 (I) 所定义，R4 和 R5 相同或不同，且各自代表具有 1 至 6 个碳原子的烷基，与 2-氨基噻唑啉在加热条件下（如需要，在惰性有机溶剂存在下）反应，以诱导环缩合，或 (b) 如果需要，在惰性有机溶剂存在下，在碱金属烷氧化物存在下进行所述缩合反应，并用酸中和生成的烯醇盐。 (b) 的反应产物与酸反应。 本发明还提供了几种制备其烯醇衍生物的工艺。 噻唑并(3,2-a)嘧啶及其烯醇衍生物和酸加成化合物可用于调节温血动物的免疫功能。
• HETEROCYCLIC AMINES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：EP0480939A1

  公开（公告）日：1992-04-22
• US4421914A
  申请人：——

  公开号：US4421914A

  公开（公告）日：1983-12-20
• US5273975A
  申请人：——

  公开号：US5273975A

  公开（公告）日：1993-12-28