2-氨基丙二酸二甲酯 | 53704-09-9

• 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
• 中文名称: 2-氨基丙二酸二甲酯
• 英文名称: dimethyl 2-aminomalonate
• 英文别名: dimethyl aminomalonate；2-aminomalonic acid dimethyl ester；dimethyl 2-aminopropanedioate
• CAS: 53704-09-9
• 化学式: C₅H₉NO₄
• mdl: MFCD00829425
• 分子量: 147.131
• InChiKey: MHDFJESNGMDHQD-UHFFFAOYSA-N

物化性质

• 沸点：
  155.7±20.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  2-氨基丙二酸二甲酯 在 氢气 作用下， 180.0 ℃ 、9.5 MPa 条件下， 以96%的产率得到丝氨醇
  参考文献：
  名称：

  一种非贵金属连续加氢还原制备丝氨醇的方法

  摘要：

  本发明属于有机合成反应领域，公开了一种非贵金属连续加氢还原制备丝氨醇的方法，其特征在于包括以下步骤：将丙二酸二甲酯亚经过硝化和还原，制备得出2‑氨基‑1,3‑丙二酸二甲酯；将包括有2‑氨基‑1,3‑丙二酸二甲酯、反应催化剂、非均相金属型负载催化剂的原料加入到反应器中进行氧化还原反应，得到混合溶液，在制得的混合溶液中加氢气发生反应，制得产品2‑氨基‑1,3‑丙二醇。本发明改用普通非均相金属铜锌基合金的三元至四元催化剂，大大提高了反应收率，降低了反应压力、提高了反应的安全性、降低了生产成本，为一种清洁、高效、安全、环保、连续的新型加氢工艺技术。

  公开号：

  CN109535014A
• 作为产物：
  描述：

  丙二酸二甲酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-氨基丙二酸二甲酯
  参考文献：
  名称：

  Porphyrins with exocyclic rings. 2. Synthesis of geochemically significant tetrahydrobenzoporphyrins from 4,5,6,7-tetrahydro-2H-isoindoles

  摘要：

  Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum. Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins. Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described. Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone. Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield. Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and/or 37b gave a series of a,c-biladiene dihydrobromides. Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15% sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield. This work provides a general route for the synthesis of these important porphyrin molecular fossils.

  DOI：

  10.1021/jo00044a013

文献信息

• Scaffold-Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin-3,2′-oxindoles] with Structural Diversity through Catalytic Isatin-Derived 1,3-Dipolar Cycloadditions
  作者：Feng Shi、Zhong-Lin Tao、Shi-Wei Luo、Shu-Jiang Tu、Liu-Zhu Gong

  DOI：10.1002/chem.201200358

  日期：2012.5.29

  Catalytic asymmetric construction of the biologically important spiro[pyrrolidin‐3,2′‐oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee) has been established by using an organocatalytic 1,3‐dipolar cycloaddition of isatin‐based azomethine ylides. This protocol represents the first example of catalytic asymmetric 1,3‐dipolar

  通过使用有机催化1,3，已经建立了具有重要立体选择性（具有高达99：1 dr，98％ee的连续性）的具有重要季螺立体构象中心的重要生物学螺旋[pyrrolidin-3,2'-oxindole]支架的催化不对称结构。 基于靛红的甲亚胺烷基化物的偶极环加成。该方案代表了催化不对称1,3-偶极环加成反应的第一个例子，涉及不对称环酮就地生成的甲亚胺基化物。另外，对反应的过渡态进行了理论计算以了解立体化学。使用这些螺[吡咯烷酮-3,2'-羟吲哚]的初步生物测定显示，几种化合物对SW116细胞显示中等程度的细胞毒性。
• Electron field emission from Ar⁺ ion-treated thick-film carbon paste
  作者：Gillian A. M. Reynolds、Lap-Tak Cheng、Robert Bouchard、Paul Moffett、Howard Jones、Linda F. Robinson、S. Ismat Shah、Daniel I. Amey

  DOI：10.1557/jmr.2002.0375

  日期：2002.10

  Ion bombardment was used to produce electron-emitting microscale features on surfaces of thick films printed with carbon pastes. This technology can potentially enable the development of large-area field emission displays. Systematic investigations using microscopy and electron field emission experiments have demonstrated a close link among paste formulation, ion processing parameters, and the development of surface microstructures. These investigations were also useful in understanding the fundamentals of microstructure formation under ion bombardment and the field emission characteristics of the carbon-based emitters. Several device concepts aimed toward achieving a low-voltage switchable triode were also tested with varying degrees of success. In this paper, we discuss various technological issues related to the materials, processes, and devices.

  利用离子轰击技术在印有碳浆的厚膜表面产生电子发射微观特征。这项技术有可能实现大面积场发射显示器的开发。利用显微镜和电子场发射实验进行的系统研究表明，浆料配方、离子处理参数和表面微结构的发展之间存在密切联系。这些研究还有助于了解离子轰击下微结构形成的基本原理以及碳基发射器的场发射特性。我们还测试了几种旨在实现低压可切换三极管的器件概念，并取得了不同程度的成功。在本文中，我们讨论了与材料、工艺和器件有关的各种技术问题。
• Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: access to the synthesis of chromeno[4,3-<i>b</i>]pyrroles
  作者：Xiaohu Li、You Huang

  DOI：10.1039/d1cc04199a

  日期：——

  A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.

  已开发出膦催化的 γ-烯丙酸乙烯酯与醛亚胺酯的级联 (2+3)/(2+4) 环化反应，以提供一系列包含三个连续立体中心的色基[4,3- b ] 吡咯衍生物. 该方法在温和条件下具有良好的收率、优异的化学选择性和非对映选择性。
• Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
  作者：P Brungs、K Danielmeier、J Jakobi、C Nothhelfer、A Stahl、A Zietlow、E Steckhan

  DOI：10.1051/jcp/1996930575

  日期：——

  Three different electrochemical methods have been applied for the synthesis of chiral building blocks for diastereoselective amidoalkylation reactions. These are A. the direct anodic α-methoxylation of amides and carbamates; B. anodic methoxylative decarboxylation of α-amino acid derivatives (Hofer-Moest reaction) C. indirect NaCl mediated anodic α-methoxylation of α-amino acid derivatives. The application of these building blocks for the synthesis of enantiomerically pure α-amino acids, dichiral 1,2-amino alcohols and chiral 1,3-diamines is described.

  已经应用了三种不同的电化学方法来合成用于二分立体选择性氨基烷基化反应的手性构建块。这些方法包括：A. 酰胺和碳酸酯的直接阳极α-甲氧基化；B. α-氨基酸衍生物的阳极甲氧基化脱羧（Hofer-Moest反应）C. 间接NaCl介导的α-氨基酸衍生物的阳极α-甲氧基化。描述了这些构建块在合成手性纯α-氨基酸、二分手性1,2-氨基醇和手性1,3-二胺中的应用。
• Organocatalytic Enantioselective 1,3‐Dipolar [6+4] Cycloadditions of Tropone
  作者：Giulio Bertuzzi、David McLeod、Lisa‐Marie Mohr、Karl Anker Jørgensen

  DOI：10.1002/chem.202003329

  日期：2020.12

  A highly stereoselective 1,3‐dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2‐aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2‐aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series

  已经开发出一种高度立体选择性的1,3-偶极[6 + 4]环加成反应成桥连的双氮杂双环[4.3.1]癸烷骨架，可以在温和条件下，在手性磷酸催化剂的存在下，使醛，2-氨基丙二酸酯和tropone反应。证明了适用于一系列醛和2-氨基丙二酸酯的范围，反应以高收率，> 95：5 dr和高达99％  ee进行。提出了一系列的转换，以及一个机械的建议。