butane-1,1,4,4-tetracarboxylic acid tetraethyl ester | 4450-43-5

• 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
• 英文名称: butane-1,1,4,4-tetracarboxylic acid tetraethyl ester
• 英文别名: tetraethyl butane-1,1,4,4-tetracarboxylate
• CAS: 4450-43-5
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: KNTOEBNUVAIYKF-UHFFFAOYSA-N

物化性质

• 沸点：
  170-180 °C(Press: 2 Torr)
• 密度：
  1.1094 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2917190090

反应信息

• 作为反应物：
  描述：

  butane-1,1,4,4-tetracarboxylic acid tetraethyl ester 在 sodium ethanolate 作用下， 生成 顺式-环丁烷-1,2-二羧酸
  参考文献：
  名称：

  Lennon; Perkin, Journal of the Chemical Society, 1928, p. 1524

  摘要：

  DOI：
• 作为产物：
  描述：

  tetraethyl ethylenebisbromomalonate 在 水 、 silver(l) oxide 作用下， 以 乙醇 为溶剂， 生成 butane-1,1,4,4-tetracarboxylic acid tetraethyl ester
  参考文献：
  名称：

  Reactions of alkylenebisbromomalonates with nucleophiles

  摘要：

  Treatment of alkylenebisbromomalonates with nucleophiles (AcOK, AgOH, KHCO3, 1,8-diazabicyclo[5.4.0]undec-7-ene, or Ph(3)P) results mainly in their debromination to give cycloalkane-1,1,2,2-tetracarboxylates. When H2O and acids are present, the reaction gives products of the substitution of one or two bromine atoms by hydrogen. Alkaline hydrolysis results in oxacycloalkane-alpha,alpha,alpha',alpha'-tetracarboxylic acids. The reaction mechanism is discussed.

  DOI：

  10.1007/bf00700171

文献信息

• Self-assembly of cage structures. Paper 12: The synthesis and crystal structures of 2,5-diazabicyclo[2.2.2]octane-3,6-dione-1,4-dicarboxylic acids and their diesters
  作者：Konstantin A. Lyssenko、Denis A. Lenev、Remir G. Kostyanovsky

  DOI：10.1016/s0040-4020(02)01022-0

  日期：2002.10

  determination. Packing of the diacids (±)-2 and (−)-2 dihydrates differed from that of esters, with H2O molecules linking homochiral spirals, into corrugated homochiral layers, observed in both structures. The crystal structure of enantiomeric diester (−)-1 contained spirals similar to those observed in diacids with participation of the ester carbonyl groups in H-bonding.

  描述了外消旋和对映体2,5-二氮杂双环[2.2.2]辛烷-3,6-二酮-二羧酸及其二酯的合成，作为超分子化学的功能化构建基块。研究表明，具有外消旋涂层的R 2 2（8）图和带有非极性涂层的分子“砖墙”的杂手性H键曲折带是外消旋二烷基2，5-二氮杂双环[2.2]晶体结构中的持久且稳定的基序。 0.2]辛烷-3,6-二酮-1,4-二羧酸酯（1，5，11）。该稳定性通过准外消旋体[CD（-）230] -1 · 4的形成和晶体结构的确定来确认。二酸（±）-2和（-）- 2的堆积二水合物与酯的二水合物不同，H 2 O分子将同手性螺旋连接成波纹状的同手性层，在两种结构中均观察到。对映体二酯（-）- 1的晶体结构具有类似于在二酸中观察到的螺旋，并且在H键中酯羰基的参与。
• Nitric Oxide Inactivates Glyoxalase I in Cooperation with Glutathione
  作者：A. Mitsumoto、K.-R. Kim、G. Oshima、M. Kunimoto、K. Okawa、A. Iwamatsu、Y. Nakagawa

  DOI：10.1093/oxfordjournals.jbchem.a022797

  日期：2000.10.1

  We previously found that glyoxalase I (Glo I) is inactivated upon exposure of human endothelial cells to extracellular nitric oxide (NO), and this event correlates with an increase in its pI on two-dimensional gels. In this study, we demonstrate that NO can modulate Glo I activity in cooperation with cellular glutathione (GSH). Severe depletion of intracellular GSH prevents the inactivation of Glo I in response to NO, although such depletion enhances the inactivation of glyceraldehyde-3-phosphate dehydrogenase (G3PDH), a well-known enzyme susceptible to NO-induced oxidation. S-Nitrosoglu-tathione (GSNO), an adduct of GSH and NO, lowers the activity of purified human Glo I, while S-nitrosocysteine (CysNO) inactivates the enzyme only in the presence of GSH. This indicates that a dysfunction in Glo I would require the formation of GSNO in situ. Competitive inhibitors of Glo I, S-(4-bromobenzyl)glutathione and its membrane-permeating form, completely abolish the NO action in vitro and inside cells, respectively. Taken together, these results reveal that Glo I can interact directly with GSNO, and that the interaction converts Glo I into an inactive form. Moreover, the data suggest that the substrate recognition site of Glo I might be involved in the interaction with GSNO.

  我们之前发现，人类内皮细胞暴露于细胞外一氧化氮（NO）时，糖醛酸酶 I（Glo I）被失活，这一事件与其在二维胶上的等电点（pI）增加相关。在本研究中，我们证明 NO 可以与细胞内谷胱甘肽（GSH）合作调节 Glo I 活性。严重耗竭细胞内 GSH 会阻止 Glo I 对 NO 的失活，尽管这种耗竭会增强醛糖-3-磷酸脱氢酶（G3PDH）的失活，后者是一种已知对 NO 引起的氧化敏感的酶。S-亚硝基谷胱甘肽（GSNO）是 GSH 和 NO 的加合物，可降低纯化人类 Glo I 的活性，而 S-亚硝基半胱氨酸（CysNO）仅在存在 GSH 的情况下失活该酶。这表明 Glo I 的功能障碍需要在体内形成 GSNO。Glo I 的竞争抑制剂 S-(4-溴苄基)谷胱甘肽及其膜穿透形式分别在体外和细胞内完全消除 NO 的作用。综上所述，这些结果表明 Glo I 可以直接与 GSNO 互作，并且这种互作将 Glo I 转化为一种失活形式。此外，这些数据还暗示 Glo I 的底物识别位点可能参与与 GSNO 的互作。
• Syntheses of Polydifluoroboryl Chelate Compounds
  作者：Jung-Hwan Kim、Young-Il Kim

  DOI：10.2174/157017811795038322

  日期：2011.3.1

  A number of BF2-chleate compounds were developed based on 4,6-dichloropyrimidine. The electron withdrawing ability of the -BF2 group markedly enhances the reactivity of the chlorides within chloropyrimidine. Consequently the BF2-chelate compounds can be modified in a variety of ways by nucleophilic substitutions. The compounds prepared in this work consist of 4,6-dichloropyrimidine and BF2-chelate moieties separated by methylene chains of tunable lengths. Such a versatile series of compounds may provide an opportunity to study the intramolecular energy transfer processes with respect to the donor-acceptor distances. Also it is suggested that the present BF2-chelate compounds will be useful for developing various types of energy/electron transfer systems and fluorescent materials.

  以 4,6-二氯嘧啶为基础，开发出了多种 BF2-氯酸盐化合物。-BF2基团的退电子能力显著提高了氯嘧啶中氯化物的反应活性。因此，BF2-螯合物可以通过亲核取代以多种方式进行修饰。本研究制备的化合物由 4,6-二氯嘧啶和 BF2-螯合物组成，中间有长度可调的亚甲基链分隔。这种多用途的化合物系列为研究分子内能量传递过程与供体-受体距离的关系提供了机会。此外，目前的 BF2-螯合物还有助于开发各种类型的能量/电子转移系统和荧光材料。
• Bioerodible poly(ortho esters) from dioxane-based di(ketene acetals), and block copolymers containing them
  申请人：——

  公开号：US20040096506A1

  公开（公告）日：2004-05-20

  Bioerodible poly(ortho esters) useful as orthopedic implants or vehicles for the sustained delivery of pharmaceutical, cosmetic and agricultural agents from dioxane-based di(ketene acetals). Block copolymers contain these bioerodible poly(ortho esters). These block copolymers have both hydrophilic and hydrophobic blocks. They form micelles in aqueous solution, making them suitable for encapsulation or solubilization of hydrophobic or water-insoluble materials; and they also form bioerodible matrices for the sustained release of active agents.

  生物可降解的聚酯类（ortho esters）可用作骨科植入物或从二噁烷基二（酮酸酯）中提供药物、化妆品和农业剂量的持续释放载体。这些生物可降解的聚酯类是由含有这些聚酯类的嵌段共聚物组成的。这些嵌段共聚物具有亲水和疏水的嵌段。它们在水溶液中形成胶束，适用于封装或溶解疏水或不溶于水的材料；它们还形成生物可降解的基质，用于持续释放活性成分。
• [EN] METHOD OF PREPARING DI(KETENE ACETALS)<br/>[FR] PROCEDE DE PREPARATION DE DI(CETENE ACETALS)
  申请人：A P PHARMA INC

  公开号：WO2004046074A1

  公开（公告）日：2004-06-03

  Di(ketene acetals) are prepared by photoisomerizing the corresponding di(vinyl acetals).

  Di（酮烯缩醛）是通过光异构化相应的双（乙烯醇醚）制备的。