acetoacetic acid β-propoxyethyl ester | 39562-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: acetoacetic acid β-propoxyethyl ester
• 英文别名: propoxyethyl 3-oxobutanoate；acetoacetic acid 2-propoxyethyl ester；Acetessigsaeure-2-(propoxy)ethylester；2-Propoxyethyl acetoacetate；2-propoxyethyl 3-oxobutanoate
• CAS: 39562-61-3
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: BBBJXPCSKOPGLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetoacetic acid β-propoxyethyl ester 在 哌啶 、 氢氧化钾 、 溶剂黄146 、 磷脂酶B 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 29.5h， 生成 (+)-3-methyl 5-(2-propoxyethyl) (4S)-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Effect of Acyl Chain Length and Branching on the Enantioselectivity of Candida rugosa Lipase in the Kinetic Resolution of 4-(2-Difluoromethoxyphenyl)-Substituted 1,4-Dihydropyridine 3,5-Diesters

  摘要：

  Since 2,6-dimethyl-4-aryl-1,4-dihydropyridine 3,5-diesters themselves are not hydrolyzed by commercially available hydrolases, derivatives with spacers containing a hydrolyzable group were prepared. Seven acyloxymethyl esters of 5-methyl- and 5-(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate were synthesized and subjected to Candida rugosa lipase (CRL) catalyzed hydrolysis in wet diisopropyl ether. A methyl ester at the 5-position and a long or branched acyl chain at C3 gave the highest enantiomeric ratio (E values). The most stereoselective reaction (E = 21) was obtained with 3-[(isobutyryloxy)methyl] 5-methyl 4-(2-difluoromethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, and this compound was used to prepare both enantiomers of 3-methyl 5-(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate. The absolute configuration of the enzymatically produced carboxylic acid was established to be 4R by X-ray crystallographic analysis of its 1-(R)-phenylethyl amide.

  DOI：

  10.1021/jo0104025
• 作为产物：
  描述：

  双乙烯酮 、 乙二醇单正丙醚 在 三乙胺 作用下， 生成 acetoacetic acid β-propoxyethyl ester
  参考文献：
  名称：

  Bossert; Horstmann; Meyer, Arzneimittel-Forschung/Drug Research, 1979, vol. 29, # 2, p. 226 - 229

  摘要：

  DOI：

文献信息

• Pharmaceutical compositions containing unsymmetrical esters of
  申请人：Farbenfabriken Bayer AG

  公开号：US03932645A1

  公开（公告）日：1976-01-13

  Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acids as the active ingredient and methods of using same. The said ingredients are unsymmetrical 1,4-dihydropyridine 3,5-dicarboxylates which are substituted at position-4 of the dihydropyridine nucleus by phenyl which contains at least one nitro, cyano, azido, alkylthio, or alkylsulphonyl substituent. The compositions have a cardiovascular activity which makes them useful for effecting coronary vascular dilation and, also, they have utility in the treatment of hypertension.

  含有不对称酯化的1,4-二氢吡啶-3,5-二羧酸的药物组合物作为活性成分，并使用方法。所述成分是在二氢吡啶核的4位被苯基取代的不对称1,4-二氢吡啶-3,5-二羧酸酯，该苯基含有至少一个硝基、氰基、叠氮基、烷基硫醚或烷基磺酰基取代基。这些组合物具有心血管活性，可用于促进冠状血管扩张，并且在治疗高血压方面具有用途。
• Synthesis of new water-soluble dihydropyridine vasodilators.
  作者：MASARU IWANAMI、TADAO SHIBANUMA、MASAHARU FUJIMOTO、RYUTARO KAWAI、KAZUHARU TAMAZAWA、TOICHI TAKENAKA、KOZO TAKAHASHI、MASUO MURAKAMI

  DOI：10.1248/cpb.27.1426

  日期：——

  Several kinds of water-soluble dihydropyridine vasodilators were prepared and their vasodilating activities were evaluated. Among them, 2-(N-benzyl-N-methylamino)-ethyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate hydrochloride (YC-93) was found to have outstanding activity and bioavailability. Various synthetic routes for this compound were examined.

  制备了几种水溶性二氢吡啶血管扩张剂，并评估了它们的血管扩张活性。其中，2-（N-苯基-N-甲基氨基）-乙基-甲基-2, 6-二甲基-4-（m-硝基苯基）-1, 4-二氢吡啶-3, 5-二羧酸盐盐酸盐（YC-93）被发现具有出色的活性和生物利用度。对该化合物的各种合成路线进行了研究。
• Alkoxy-and phenoxy alkyl esters of
  申请人：——

  公开号：US04845109A1

  公开（公告）日：1989-07-04

  Novel compounds, that is, alkoxy- and phenoxy-alkyl esters of 2,6-dimethyl-4-(2-difluoromethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxy li c acid have the following general formula useful for producing hypotensive and vasodilation effects. ##STR1##

  小说化合物，即2,6-二甲基-4-(2-二氟甲氧基苯基)-1,4-二氢吡啶-3,5-二羧酸的烷氧基和苯氧基烷酯具有以下通用公式，可用于产生降压和血管扩张效果。 ##STR1##
• Method of combatting coronary and vascular diseases
  申请人：Bayer Aktiengesellschaft

  公开号：US04532248A1

  公开（公告）日：1985-07-30

  1,4-Dihydropyridines of the formula ##STR1## in which n is 0,1 or 2, and R.sup.1 to R.sup.7 can have a wide variety of meanings, which possess inotropic action, and many of which are new, are useful in increasing the influx of Ca.sup.++ into cells, particularly in combatting coronary and vascular diseases, hypertension swelling in the mucous membranes and diseases involving increased blood sugar or an incorrect salt and fluid balance.

  公式为##STR1##的1,4-二氢吡啶，其中n为0、1或2，R.sup.1到R.sup.7可以有各种含义，具有肌力作用，其中许多是新的，有助于增加Ca.sup.++进入细胞，特别是对抗冠状动脉和血管疾病、高血压、粘膜肿胀和涉及血糖增高或不正确的盐和液体平衡的疾病。
• Design and Synthesis of Hepatitis B Virus (HBV) Capsid Assembly Modulators and Evaluation of Their Activity in Mammalian Cell Model
  作者：Karina Spunde、Brigita Vigante、Unda Nelda Dubova、Anda Sipola、Irena Timofejeva、Anna Zajakina、Juris Jansons、Aiva Plotniece、Karlis Pajuste、Arkadij Sobolev、Ruslan Muhamadejev、Kristaps Jaudzems、Gunars Duburs、Tatjana Kozlovska

  DOI：10.3390/ph15070773

  日期：——

  The most efficient were the HAP class compounds—dihydropyrimidine 5-carboxylic acid n-alkoxyalkyl esters, which induced the formation of incorrectly assembled capsid products and their accumulation within the cells. HBc product accumulation in the cells was not detected with the reference HAP compound Bay 41-4109, suggesting different modes of action. A significant antiviral effect and substantially

  背景：衣壳组装调节剂 (CAM) 已成为一类有前途的抗病毒药物。我们研究了 21 种新设计和合成的 CAM，包括杂芳基二氢嘧啶化合物 (HAP)、它们的类似物和标准化合物对乙型肝炎病毒 (HBV) 衣壳组装的影响。方法：由外源递送的重组甲病毒 RNA 复制子驱动的 HBV 核心 (HBc) 基因的细胞质表达被用于在哺乳动物细胞中高水平生产全长 HBc 蛋白。通过天然琼脂糖凝胶免疫印迹分析、电子显微镜检查和抑制 HepG2.2.15 HBV 产生细胞系中的病毒粒子分泌来评估 HBV 衣壳组装。诱导拟合对接模拟用于模拟合成化合物和 HBc 的结构关系。结果：n-烷氧基烷基酯，其诱导错误组装的衣壳产物的形成及其在细胞内的积累。参考 HAP 化合物 Bay 41-4109 未检测到细胞中的 HBc 产物积累，表明不同的作用模式。两种合成化合物显示出显着的抗病毒作用和显着降低的毒性。结论：两种新的 HAP