β-Aminocrotonic acid dodecyl ester | 43107-10-4

• 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: β-Aminocrotonic acid dodecyl ester
• 英文别名: dodecyl 3-aminobut-2-enoate；3-aminobut-2-enoic acid dodecyl ester；3-Amino-but-2-enoic acid dodecyl ester
• CAS: 43107-10-4
• 化学式: C₁₆H₃₁NO₂
• 分子量: 269.428
• InChiKey: PAAFSFGSAAGRCK-UHFFFAOYSA-N

物化性质

• 沸点：
  379.0±15.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  β-Aminocrotonic acid dodecyl ester 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 甲醇 、 丙醇 为溶剂， 反应 0.23h， 生成 1,1`-[(3,5-bis(dodecyloxycarbonyl)-4-[4-(trifluoromethyl)phenyl]-1,4-dihydropyridin-2,6-diyl)bis(methylene)] bis(pyridinium) bromide
  参考文献：
  名称：

  使用NMR和ITC技术研究单核苷酸与1,4-二氢吡啶囊泡的相互作用†

  摘要：

  1,4-二氢吡啶（DHP）囊泡作为药物输送剂的使用可以改善核苷和核苷酸前药通过细胞膜的扩散而不会降解。不同NMR研究：在旋转框架自旋-晶格弛豫（Ť 1 ρ），饱和转移双差（STDD），1个1 H NMR化学位移滴定，以及等温滴定量热法（ITC）的实验中，显示单核苷酸结合1 ，4-DHP囊泡。研究了单核苷酸的结构以及1,4-DHP的衍生物对络合参数的影响。

  DOI：

  10.1039/c8nj00160j

文献信息

• Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates
  作者：Brigita Vigante、Martins Rucins、Aiva Plotniece、Karlis Pajuste、Iveta Luntena、Brigita Cekavicus、Egils Bisenieks、Rufus Smits、Gunars Duburs、Arkadij Sobolev

  DOI：10.3390/molecules201119697

  日期：——

  ethoxycarbonylmethyl esters of 1,4-dihydropyridines were directly converted into carbamoylmethyl esters in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in good to excellent yields under mild conditions. The use of TBD is crucial for the successful aminolysis of ethoxycarbonylmethyl ester of 1,4-dihydropyridines with secondary amines as without it the reaction does not proceed at all. The aminolysis reaction

  在温和条件下，在 1,5,7-三氮杂双环 [4.4.0]dec-5-烯 (TBD) 存在下，1,4-二氢吡啶的乙氧基羰基甲酯直接转化为氨基甲酰基甲酯，产率良好至极好。TBD 的使用对于 1,4-二氢吡啶的乙氧基羰基甲酯与仲胺的成功氨解至关重要，因为没有它，反应根本不会进行。氨解反应区域选择性地进行，因为与 1,4-二氢吡啶循环共轭的烷基酯不参与反应。筛选其他含氮碱，如三乙胺 (TEA)、吡啶、4-(N,N-二甲氨基)吡啶 (DMAP)、1,8-二氮杂双环[5.4.0]十一碳烯 (DBU)、 1,5-二氮杂双环[4.3.0]非5-烯(DBN)、咪唑、四甲基胍(TMG)和7-甲基-1,5,7-三氮杂双环[4.4。
• Synthesis of 1,4-Dihydropyridine-5-phosphonates and Their Calcium-Antagonistic and Antihypertensive Activities. Novel Calcium-Antagonist 2-(Benzyl(phenly)amino)ethyl 5-(5,5-Dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate Hydrochloride Ethanol(NZ-105) and Its Crystal Structure.
  作者：Ryozo SAKODA、Yoshimasa KAMIKAWAJI、Kiyotomo SETO

  DOI：10.1248/cpb.40.2362

  日期：——

  The effect of the 3-carboxylic-ester variation in 2, 2-dimethyltrimethylene 3-alkoxycarbonyl-4-aryl-1, 4-dihydro-2, 6-dimethyl-5-pyridinephosphonates (1) was investigated with relation to the calcium-antagonistic and antihypertensive activities : the analogs contaning the alkyl groups of not more than 12 carbons and an amino functionality in the carboxylic-ester moiety were synthesized to be examined for biological activities. Among them, 2-[benzyl(phenyl)amino]-ethyl 5(5, 5-dimethyl-2-oxo-1, 3, 2-dioxaphosphorinan-2-yl)-1, 4-dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3-phridine-carboxylate hydrochloride ethanol (NZ-105) showed particularly beneficial activities and was selected for further pharmacological studies and clinical development. Some aspects of the structure-activity relationships and solid-state structure of NZ-105 by X-ray crystallographic analysis were described.

  研究了3-羧酸酯变体在2,2-二甲基三甲基烯-3-烷氧羰基-4-芳基-1,4-二氢-2,6-二甲基-5-吡啶膦酸酯(1)中与钙拮抗和降压活性相关的影响：合成了含有不超过12个碳的烷基和羧酸酯部分含有氨基功能团的类似物，以检测其生物活性。其中，2-[苄基(苯基)氨基]乙基5-(5,5-二甲基-2-氧-1,3,2-二氧膦杂环己烷-2-基)-1,4-二氢-2,6-二甲基-4-(3-硝基苯基)-3-吡啶羧酸酯盐酸盐乙醇(NZ-105)显示出特别有益的活性，并被选中进行进一步的药理学研究和临床开发。描述了通过X射线晶体学分析获得的NZ-105的结构-活性关系和固态结构的一些方面。
• Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative
  作者：Karlis Pajuste、Aiva Plotniece、Kintija Kore、Liva Intenberga、Brigita Cekavicus、Dainis Kaldre、Gunars Duburs、Arkadij Sobolev

  DOI：10.2478/s11532-010-0132-x

  日期：2011.2.1

  AbstractThe synthesis of cationic amphiphilic 1,4-dihydropyridine derivative, potential gene delivery agent is achieved via an efficient multi-step sequence. The key step of this approach is a two-component Hantzsch type cyclisation of 3-oxo-2-[1-phenylmethylidene]-butyric acid dodecyl ester and 3-amino-but-2-enoic acid dodecyl ester utilising bis(2-hydroxyethyl)ether as a solvent and 1-butyl-4-methylpyridinium

  摘要 阳离子两亲性 1,4-二氢吡啶衍生物，潜在的基因传递剂的合成是通过高效的多步骤序列实现的。该方法的关键步骤是利用双（2-羟乙基）酯对 3-氧代-2-[1-苯基亚甲基]-丁酸十二烷基酯和 3-氨基-丁-2-烯酸十二烷基酯进行双组分 Hantzsch 型环化反应。 )醚作为溶剂，1-丁基-4-甲基氯化吡啶鎓作为催化剂。在 1,4-DHP 环的 3 和 5 位具有长烷基酯链的 1,4-二氢吡啶衍生物——3,5-双（十二烷氧基羰基）-2,6-二甲基-4-苯基-1,4-二氢吡啶相对于经典的 Hantzsch 合成以显着更高的产率获得。将该化合物溴化，然后用吡啶亲核取代溴，得到所需的阳离子两亲性 1,4-二氢吡啶。
• Synthesis and pharmacological activity of some derivatives of condensed 1,4-dihydropyridines
  作者：R. O. Vitolinya、É. I. Stankevich、É. É. Grinshtein、A. Ya. Dreimane

  DOI：10.1007/bf00765716

  日期：1981.1
• Synthesis and antihypertensive activity evaluation in spontaneously hypertensive rats of nitrendipine analogues
  作者：Kai Zhou、Xiao-meng Wang、Yi-zhi Zhao、Yong-xiao Cao、Qiang Fu、San-qi Zhang

  DOI：10.1007/s00044-010-9477-0

  日期：2011.11

  The antihypertensive activity of nitrendipine analogues can be improved by properly lengthening its alkyl chain in 3- or 5-position. Nitrendipine and its seven analogues were synthesized, and their antihypertensive activities in spontaneously hypertensive rats (SHR) were evaluated by ig administration. It was found that 5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [(+/-)-5] exhibited the strongest antihypertensive effect amongst eight compounds. (+)-5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [(+)-5] was also prepared. Antihypertensive activities of (+/-)-5 and (+)-5 in SHR were compared. The results showed that (+/-)-5 and (+)-5 had a higher potency than nitrendipine, and (+)-isomer was 1.79-fold the raceme at a dose of 2 mg/kg.