allyl 3-aminocrotonate | 14205-41-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: allyl 3-aminocrotonate
• 英文别名: prop-2-enyl 3-aminobut-2-enoate
• CAS: 14205-41-5
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: ZQQKPYARJDTPAI-UHFFFAOYSA-N

物化性质

• 沸点：
  122 °C(Press: 0.13 Torr)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  allyl 3-aminocrotonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 27.0h， 生成 [allyl-2,3-(3)H]-MN-92019
  参考文献：
  名称：

  Synthesis of [allyl-2,3-3H]-MN-9201

  摘要：

  Key step of the synthesis of calcium antagonist MN-9201 was the cyclizing addition of the allyl-3-amino-crotonate onto methyl 2-[(3-nitrophenyl) methylene]-3-oxobutanoate. It was then used to synthesize [Allyl-2,3-H-3]-MN-9201 by the catalytic addition of tritium gas. Its radiochemical purity and specific activity were 98% and 2.1TBq/mmol, respectively.

  DOI：

  10.1002/(sici)1099-1344(1998090)41:9<785::aid-jlcr133>3.0.co;2-d
• 作为产物：
  描述：

  乙酰乙酸烯丙酯 在 氨 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到allyl 3-aminocrotonate
  参考文献：
  名称：

  Synthesis of [allyl-2,3-3H]-MN-9201

  摘要：

  Key step of the synthesis of calcium antagonist MN-9201 was the cyclizing addition of the allyl-3-amino-crotonate onto methyl 2-[(3-nitrophenyl) methylene]-3-oxobutanoate. It was then used to synthesize [Allyl-2,3-H-3]-MN-9201 by the catalytic addition of tritium gas. Its radiochemical purity and specific activity were 98% and 2.1TBq/mmol, respectively.

  DOI：

  10.1002/(sici)1099-1344(1998090)41:9<785::aid-jlcr133>3.0.co;2-d

文献信息

• Tailor-made synthesis of fully alkylated/arylated nicotinates by FeCl₃-mediated condensation of enamino esters with enones
  作者：Sho Hirai、Yurie Horikawa、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1039/c7cc00051k

  日期：——

  A new method for synthesizing polyalkylated/arylated nicotinates is established using a condensation of enamino esters with enones in the presence of FeCl3. This method facilitates the introduction of alkyl or...

  在FeCl3存在下，使用烯胺酯与烯酮的缩合，建立了一种合成多烷基化/芳基烟酸酯的新方法。这种方法有助于引入烷基或...
• Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.
  作者：IWAO MORITA、KATSUTOSHI KUNIMOTO、MASAMI TSUDA、SHIN-ICHI TADA、MASAHIRO KISE、KIYOSHI KIMURA

  DOI：10.1248/cpb.35.4144

  日期：——

  A series of 1, 4-dihydropyridine-5-cyclic phosphonate derivatives, designed as analogues of 1, 4- dihydropyridine-3, 5-dicarboxylate calcium antagonists, was synthesized and examined for antihypertensive activity. Several compounds were proved to have activities superior or comparable to that of nifedipine in lowering blood pressure in normotensive and spontaneously hypertensive rats (SHR). Among these compounds, methyl 2, 6-dimethyl-5- (2-oxo-1, 3, 2-dioxaphosphorinan-2-yl) -4- (2-nitrophenyl) -1, 4-dihydropyridine-3-carboxylate (31, DHP-218) was approximately 7 times more active than nifedipine in SHR and was selected for further development and clinical evaluation. The structure-activity relationships are discussed.

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。
• Cardiovascular Profile of Xanthone-Based 1,4 Dihydropyridines Bearing a Lidoflazine Pharmacophore Fragment
  作者：Alessandra Bisi、Matteo Micucci、Silvia Gobbi、Federica Belluti、Roberta Budriesi、Angela Rampa

  DOI：10.3390/molecules23123088

  日期：——

  As a follow-up to our previous studies on differently substituted 1,4-dihydropyridines endowed with a peculiar cardiac selectivity, in this paper, a small series of hybrid compounds bearing the pharmacophore fragment of lidoflazine in position 2 or 3 on a 4-(xanthen-9-one)-dihydropyridine core was reported. Lidoflazine was selected due to our promising previously reported data, and the xanthen-9-one substituent was introduced in position 4 of the dihydropyridine scaffold based on the cardiac selectivity observed in several of our studies. The new hybrid compounds were tested to assess cardiac and vascular activities, and the data were evaluated in comparison with those previously obtained for 4-(xanthen-9-one)-dihydropyridines and lidoflazine–nifedipine hybrid compounds. The functional studies indicated an interesting peculiar selectivity for the cardiac parameter inotropy, in particular when the lidoflazine fragment was introduced in position 2 of the dihydropyridine scaffold (4a–e), and thus a possible preferential binding with the Cav 1.2 isoform of l-type calcium channels, which are mainly involved in cardiac contractility.

  作为我们之前对不同取代的1,4-二氢吡啶具有特殊心脏选择性的研究的后续，本文报告了一系列小型混合化合物，这些化合物在4-(黄酮-9-酮)-二氢吡啶核心上携带了利多氟嗪的药效团片段，该片段位于位置2或3。利多氟嗪是由于我们之前报告的有希望的数据而被选择，而黄酮-9-酮取代基是基于我们几项研究中观察到的心脏选择性，在二氢吡啶骨架的位置4引入的。对新的混合化合物进行了测试以评估其对心血管活动的影响，并将数据与先前获得的4-(黄酮-9-酮)-二氢吡啶和利多氟嗪-硝苯地平混合化合物的数据进行比较。功能研究表明，在心脏参数肌力方面存在有趣的特殊选择性，特别是当利多氟嗪片段被引入到二氢吡啶骨架的位置2时（4a-e），因此可能与主要参与心脏收缩的l-型钙通道的Cav 1.2亚型发生优先结合。
• Process for making amlodipine, derivatives therof, and precursors therefor
  申请人：——

  公开号：US20020143046A1

  公开（公告）日：2002-10-03

  Amlodipine and related analogues thereof are prepared by the following general reaction scheme: 1 R 1 and R 2 each independently represent a C 1 -C 4 alkyl group. The process provides for the formation of compounds of formula (1) in good yield and purity. Further, the compounds of formula (1) can be used as calcium channel blockers or as reference standards or reference markers for checking the purity of amlodipine.

  氨氯地平及其相关类似物是通过以下一般反应方案制备的：1R1和R2各自独立表示C1-C4烷基基团。该过程提供了以良好产率和纯度形成化合物的方法。此外，化合物的公式（1）可用作钙通道阻滞剂，或用作氨氯地平纯度检查的参考标准或参考标记。
• [EN] PROCESS FOR THE PREPARATION OF 4 -SUBSTITUTED -1, 4-DIHYDROPYRIDINES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE 1,4-DIHYDROPYRIDINES SUBSTITUÉES EN POSITION 4
  申请人：ARCH PHARMALABS LTD

  公开号：WO2012123966A1

  公开（公告）日：2012-09-20

  4-Substituted-l,4-dihydropyridines of formula I are prepared by a cycloaddition reaction in which the cyclization is driven to completion at ambient temperature optionally in water without any catalyst. For exemplary purposes, the invention is described in particular detail with respect to the preparation of felodipine of formula II. Felodipine, a vasodilator, is prepared by a cycloaddition reaction of alkyl 3- aminocrotonate with dichlorobenzylidene under reaction conditions whereby the product crystallizes out of the reaction solution and may be directly isolated by filtration.

  通过环加成反应制备公式I的4-取代-1,4-二氢吡啶，该环化反应在室温下可在水中无需任何催化剂的情况下完全进行。为了举例说明，本发明特别详细地描述了制备公式II的非洛地平的方法。非洛地平是一种血管扩张剂，通过烷基3-氨基丙烯酸酯与二氯苯甲醛进行环加成反应制备，反应条件下产物结晶出来并可通过过滤直接分离。