dimethyl 2-(prop-2-en-1-yl)butanedioate | 1069-40-5

• 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: dimethyl 2-(prop-2-en-1-yl)butanedioate
• 英文别名: methyl 3-(methoxycarbonyl)-5-hexenoate；dimethyl 2-(2-propenyl)butanedioate；dimethyl 2-allylsuccinate；Allylbernsteinsaeure-dimethylester；Dimethyl 2-prop-2-enylbutanedioate
• CAS: 1069-40-5
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: XEXRJAYCKWSRCL-UHFFFAOYSA-N

物化性质

• 沸点：
  56-59 °C
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  dimethyl 2-(prop-2-en-1-yl)butanedioate 以80%的产率得到
  参考文献：
  名称：

  GUIBE-JAMPEL, E.;ROUSSEAU, G.;SALAUN, J., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 14, 1080-1081

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴丙烯 、 丁二酸二甲酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到dimethyl 2-(prop-2-en-1-yl)butanedioate
  参考文献：
  名称：

  Large Scale Structural Rearrangement of a Serine Hydrolase from Francisella tularensis Facilitates Catalysis

  摘要：

  Tularemia is a deadly, febrile disease caused by infection by the Gram-negative bacterium, Francisella tularensis. Members of the ubiquitous serine hydrolase protein family are among current targets to treat diverse bacterial infections. Herein we present a structural and functional study of a novel bacterial carboxylesterase (FTT258) from F. tularensis, a homologue of human acyl protein thioesterase (hAPT1). The structure of FTT258 has been determined in multiple forms, and unexpectedly large conformational changes of a peripheral flexible loop occur in the presence of a mechanistic cyclobutanone ligand. The concomitant changes in this hydrophobic loop and the newly exposed hydrophobic substrate binding pocket suggest that the observed structural changes are essential to the biological function and catalytic activity of FTT258. Using diverse substrate libraries, site-directed mutagenesis, and liposome binding assays, we determined the importance of these structural changes to the catalytic activity and membrane binding activity of FTT258. Residues within the newly exposed hydrophobic binding pocket and within the peripheral flexible loop proved essential to the hydrolytic activity of FTT258, indicating that structural rearrangement is required for catalytic activity. Both FTT258 and hAPT1 also showed significant association with liposomes designed to mimic bacterial or human membranes, respectively, even though similar structural rearrangements for hAPT1 have not been reported. The necessity for acyl protein thioesterases to have maximal catalytic activity near the membrane surface suggests that these conformational changes in the protein may dually regulate catalytic activity and membrane association in bacterial and human homologues.

  DOI：

  10.1074/jbc.m112.446625

文献信息

• Chemoselectivity in the conjugate addition of allylsilane to Michael acceptors
  作者：George Majetich、Ada M. Casares、D. Chapman、M. Behnke

  DOI：10.1016/s0040-4039(00)81803-1

  日期：1983.1

  The allylic carbanion species generated by treatment of allylsilane with fluoride ion undergoes highly chemoselective conjugate addition to a series of Michael acceptors for which alternative known allylation procedures proved less general.

  通过用氟离子处理烯丙基硅烷而生成的烯丙基碳负离子要经历高度化学选择性的共轭加成反应，添加到一系列迈克尔受体上，对于这些受体，其他已知的烯丙基化方法被证明不那么普遍。
• Rhodium-catalysed addition of organotrialkoxysilanes to α-substituted acrylic esters
  作者：Jonathan D. Hargrave、Jennifer Herbert、Gerwyn Bish、Christopher G. Frost

  DOI：10.1039/b606977k

  日期：——

  The cationic rhodium complex [Rh(cod)2][BF4] effectively catalyses the 1,4-addition of organotrialkoxysilanes to alpha-substituted acrylic esters. The reactions are promoted by heating in an oil-bath or more conveniently in a microwave reactor allowing rapid access to a useful range of functionalised products including 2-alkyl succinates and alpha-amino acid derivatives.

  阳离子铑配合物[Rh（cod）2] [BF4]有效地催化有机三烷氧基硅烷与α-取代的丙烯酸酯的1,4-加成反应。通过在油浴中加热或更方便地在微波反应器中加热来促进反应，从而允许快速获得有用范围的官能化产物，包括琥珀酸2-烷基酯和α-氨基酸衍生物。
• [EN] POLYHEDRAL OLIGOMERIC SILSESQUIOXANE NANOCRYSTAL STABILIZATION LIGANDS<br/>[FR] LIGANDS DE STABILISATION DE NANOCRISTAL DE SILSESQUIOXANE OLIGOMÉRIQUE POLYÉDRIQUE
  申请人：NANOSYS INC

  公开号：WO2014159936A1

  公开（公告）日：2014-10-02

  Quantum-dot binding ligands with silsesquioxane moieties are provided. The quantum-dot binding ligands include a multiplicity of amine or carboxy binding ligands in combination with silsesquioxane moieties providing improved stability for the ligated quantum dots. The ligands and coated nanostructures of the present invention are useful for close packed nanostructure compositions, which can have improved quantum confinement and/or reduced cross-talk between nanostructures.

  本发明提供了具有硅倍半氧烷部分的量子点结合配体。这些量子点结合配体包括多种胺或羧基结合配体，与硅倍半氧烷部分组合在一起，为配体化的量子点提供了改进的稳定性。本发明的配体和涂层纳米结构对于紧密堆积的纳米结构组合非常有用，这些组合可以具有改进的量子限制和/或减少纳米结构之间的串扰。
• Electrochemical coupling of activated olefins and alkyl dihalides: formation of cyclic compounds
  作者：Yu Wei Lu、Jean Yves Nedelec、Jean Claude Folest、Jacques Perichon

  DOI：10.1021/jo00295a048

  日期：1990.4
• 955. The constitution of marrubiin. Part II. Synthesis of 3-tetrahydrofurylacetaldehyde
  作者：Wesley Cocker、Peter H. Boyle

  DOI：10.1039/jr9640004972

  日期：——