二乙基(3-氧代丙基)丙二酸酯 | 19515-61-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 二乙基(3-氧代丙基)丙二酸酯
• 英文名称: diethyl 2-(3-oxo-propyl)malonate
• 英文别名: Diethyl (3-oxopropyl)malonate；diethyl 2-(3-oxopropyl)propanedioate
• CAS: 19515-61-8
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: FGQNJWQEVPVFIN-UHFFFAOYSA-N

物化性质

• 沸点：
  76-79 °C(Press: 0.04-0.07 Torr)
• 密度：
  1.0986 g/cm3
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  二乙基(3-氧代丙基)丙二酸酯 在 manganese(IV) oxide 、 次氯酸叔丁酯 、 sodium methylate 作用下， 生成 ethyl 4-oxo-7,12-dihydro-6H-indolo[2,3-a]quinolizine-3-carboxylate
  参考文献：
  名称：

  在吲哚生物碱中，其核苷为；醇苷内酰胺的结构修饰，合成和仿生转化

  摘要：

  Nauclea吲哚生物碱nauclefidine的结构根据合成研究结果被修改为分子式12，并根据所建议的生物遗传途径对长春菊酰胺内酰胺（14）进行了仿生转化。

  DOI：

  10.1016/s0040-4039(00)78505-4
• 作为产物：
  描述：

  diethyl 2-(2-(1,3-dioxolan-2-yl)ethyl)malonate 生成 二乙基(3-氧代丙基)丙二酸酯
  参考文献：
  名称：

  Sex pheromone of oriental beetle,Exomala orientalis: Identification and field evaluation

  摘要：

  A gas chromatograph coupled with a behavioral bioassay was used to identify two sex pheromone components, 7-(Z)- and 7-(E)-tetradecen-2-one of the Oriental beetle (OB), Exomala orientalis. Field experiments showed that the blend of the two isomers (Z:E, 7:1) was not significantly more attractive than the Z component alone. The best performance of traps baited with the synthetic sex pheromone was achieved when they were set with the pheromone device at 30 cm above the ground. Catches in traps baited with 1 and 10 mg were not significant[y different, but they were higher (2.9-fold) than captures in traps loaded with 0.1 mg of the pheromone. Further investigations by GC-EAD revealed the presence of a possible minor component, but the small amount of material prevented its identification. 2-(E)-Nonenol, with the same retention time as the natural product, did not affect the attractancy of the synthetic sex pheromone. GC-EAD screening of previously identified sex pheromones of scarab beetles showed that male antennae of the Oriental beetle responded to japonilure, but it showed neither synergism nor inhibition to the OB sex pheromone.

  DOI：

  10.1007/bf02059892

文献信息

• Synthesis of methaprogerol analogs
  作者：G. V. Kryshtal、G. M. Zhdankina、A. G. Konoplyannikov、V. A. Tartakovsky、E. P. Serebryakov、B. B. Smirnov、O. A. Konoplyannikova、E. V. Agaeva、S. G. Zlotina

  DOI：10.1007/s11172-012-0036-3

  日期：2012.2

  Novel synthetic approaches towards analogs of methaprogerol, the efficient wound healing drug, were developed. Several hitherto unknown compounds obtained exhibited in vivo activity similar to methaprogerol. 2-(3-Dimethylaminopropyl)-5-methylhex-4-enoic acid enhanced the efficacy of the treatment of diseases of various etiologies and different organ injuries by transplantation of mesenchymal stem cells (MSC) and MSC-derived cardiomyoblasts.

  开发了新的合成方法，用于制备类似甲基普格洛的药物，这是一种高效的伤口愈合药物。获得了几种迄今未知的化合物，它们在体内的活性与甲基普格洛相似。2-（3-二甲基氨基丙基）-5-甲基己-4-烯酸通过移植间充质干细胞（MSC）和MSC衍生的心肌成纤维细胞，增强了治疗各种病因和不同器官损伤疾病的治疗效果。
• Enantioselective Synthesis of Substituted δ-Lactones by Cooperative Oxidative N-Heterocyclic Carbene and Lewis Acid Catalysis
  作者：Srikrishna Bera、Constantin G. Daniliuc、Armido Studer

  DOI：10.1021/acs.orglett.5b01932

  日期：2015.10.16

  Efficient construction of complex cylcopentane- or cyclohexane-fused δ-lactones employing redox activation of enals using a chiral N-heterocyclic carbene and LiCl as cooperative catalysts is described. The organocascade proceeds with excellent diastereo- (>99:1) and enantioselectivity (up to >99% ee) and comprises the formation of three bonds with three contiguous stereocenters.

  描述了使用手性N-杂环卡宾和LiCl作为协同催化剂，通过烯类的氧化还原活化，高效构建复杂的环戊烷或环己烷稠合的δ-内酯的方法。有机级联反应具有出色的非对映异构体（> 99：1）和对映选择性（高达> 99％ee），并包括三个连续的立体中心的三个键的形成。
• Synthetic Studies on Spiroketal Natural Products. IV. A Stereoselective Synthesis of (3S,5S,6R,9R,Rs)-3-Benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro(5.5)undecane, a Key Intermediate for Talaromycins.
  作者：Chuzo IWATA、Naoyoshi MAEZAKI、Kohji HATTORI、Masahiro FUJITA、Yasunori MORITANI、Yoshiji TAKEMOTO、Tetsuaki TANAKA、Takeshi IMANISHI

  DOI：10.1248/cpb.41.339

  日期：——

  A dioxaspiro compound (4), a common intermediate for the synthesis of talaromycin A (1) and (-)-talaromycin B (2), was synthesized by two routes utilizing two kinds of asymmetric recognition of prochiral 1, 3-diols controlled by sulfinyl chirality, that is, firstly by acid promoted diastereoselective C-O bond fission of the bicyclic acetal (7) to give the dihydropyran derivative (6), which has an S-hydroxymethyl group at the C3-position (7→6), and secondly by diastereoselective intramolecular Michael addition of the diol (5), in which the three chiral centers at C5, C6, C9 were constructed in one step (5→4).

  二氧杂螺环化合物（4）是合成塔拉霉素A（1）和（-）-塔拉霉素B（2）的常见中间体，通过两条路线合成，利用了两种对非手性1,3-二醇的不对称识别，这种识别受硫酰基手性的控制，即首先通过酸促进的二羟基选择性C-O键断裂，将双环缩醛（7）转化为二氢吡喃衍生物（6），在C3位具有S-羟甲基（7→6），其次通过二醇（5）的二羟基选择性分子内迈克尔加成反应，在一步中构建了C5、C6、C9的三个手性中心（5→4）。
• Identification of rapid access to polycyclic systems via a base-catalyzed cascade cyclization reaction and their biological evaluation
  作者：Taotao Ling、Victor Hadi、John Bollinger、Fatima Rivas

  DOI：10.1016/j.bioorg.2020.103846

  日期：2020.6

  reaction between malonate esters and acrolein was developed to access complex polycyclic systems. This novel tandem reaction enables the simultaneous generation of up to seven new bonds and at least three new stereogenic centers. Mechanistic studies indicate a series of nucleophilic 1,4 and 1,6 Michael addition reactions occur, followed by an aldol condensation reaction, culminating in the formation of three

  丙二酸酯和丙烯醛之间的碱介导的级联反应被开发来访问复杂的多环系统。这种新颖的串联反应能够同时产生多达七个新的键和至少三个新的立体异构中心。机理研究表明，发生了一系列亲核的1,4和1,6迈克尔加成反应，随后发生醛醇缩合反应，最终形成三个稠合环。通过NMR研究表征化合物，并通过X射线分析证实立体化学。产生几克数量的这种复杂分子支架的能力使该方法有望用于药物化学研究。在本文中，我们还证明了先导化合物对人类癌细胞模型显示出有希望的抗增殖活性。
• Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes
  作者：Nandkishor Chandan、Amber L. Thompson、Mark G. Moloney

  DOI：10.1039/c2ob26423d

  日期：——

  Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic

  取代的吡咯啉可通过闭环反应来获得，该闭环反应是由稳定的烯醇酸酯在离去基团激活的肟的氮原子上进行亲核攻击而发起的，该过程可有效地胜过更常见的贝克曼重排。随后的还原提供非对映选择性地进入相应的吡咯烷。这提供了从容易获得的前体到饱和杂环系统的快速途径。