diethyl bis(methoxymethyl)malonate | 83385-58-4

• 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: diethyl bis(methoxymethyl)malonate
• 英文别名: bis-methoxymethyl-malonic acid diethyl ester；β.β'-Dimethoxy-dimethylmalonsaeure-diaethylester；Bis-methoxymethyl-malonsaeure-diaethylester；Diethyl 2-(dimethoxymethyl)malonate；diethyl 2,2-bis(methoxymethyl)propanedioate
• CAS: 83385-58-4
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: MWZYXNWXQHQNHM-UHFFFAOYSA-N

物化性质

• 沸点：
  85-86 °C(Press: 3.5 Torr)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl bis(methoxymethyl)malonate 在 吡啶 、 盐酸 、 氯化亚砜 、 lithium aluminium deuteride 、 碘代三甲硅烷 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 为溶剂， 反应 31.0h， 生成 3,3-bis(chloromethyl-d2)oxetane
  参考文献：
  名称：

  Selectively deuterated and optically active cyclic ethers

  摘要：

  DOI：

  10.1021/jo00139a049
• 作为产物：
  描述：

  氯甲基甲基醚 、 丙二酸二乙酯 在 sodium 作用下， 生成 diethyl bis(methoxymethyl)malonate
  参考文献：
  名称：

  Selectively deuterated and optically active cyclic ethers

  摘要：

  DOI：

  10.1021/jo00139a049

文献信息

• Preparation of Diethyl 2-Alkoxymethyl-, 2-Phenylselenomethyl-and 2-Phenylthiomethylmalonate
  作者：Jean-Louis Delépine、Pascal Pecquet、Marie-christine Betton、François Huet

  DOI：10.1080/00397919608005216

  日期：1996.8

  Abstract Title compounds were obtained either by alkylation of the sodium derivative of diethyl malonate or by the conjugate addition to diethyl methylenemalonate 4. When reactions with 4 were run in basic medium two successive Michael additions occured.

  摘要 通过丙二酸二乙酯的钠衍生物的烷基化或通过与亚甲基丙二酸二乙酯4的共轭加成获得标题化合物。当与4在碱性介质中进行反应时，发生了两次连续的迈克尔加成。
• 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。
• Kleber, Justus Liebigs Annalen der Chemie, 1888, vol. 246, p. 100
  作者：Kleber

  DOI：——

  日期：——
• Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles
  作者：Brad R. Henke、Andrew J. Kouklis、Clayton H. Heathcock

  DOI：10.1021/jo00052a015

  日期：1992.12

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.
• Henke Brad R., Kouklis Andrew J., Heathcock Clayton H., J. Org. Chem., 57 (1992) N 26, S 7056-7066
  作者：Henke Brad R., Kouklis Andrew J., Heathcock Clayton H.

  DOI：——

  日期：——