cyanoacetic acid 2-(2-cyanoacetoxy) ethyl ester | 89976-96-5

• 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: cyanoacetic acid 2-(2-cyanoacetoxy) ethyl ester
• 英文别名: ethylene glycol cyanoacetate；1,2-bis-cyanacetoxy-ethane；1,2-Bis-cyanacetoxy-aethan；Ethylene bis(cyanoacetate)；Ethylenglykol-1,2-di-(cyanoacetat)；2-(2-cyanoacetyl)oxyethyl 2-cyanoacetate
• CAS: 89976-96-5
• 化学式: C₈H₈N₂O₄
• mdl: MFCD00045635
• 分子量: 196.163
• InChiKey: UASCOHMZKHIVQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyanoacetic acid 2-(2-cyanoacetoxy) ethyl ester 、 邻甲氧基苯甲醛 生成
  参考文献：
  名称：

  Takada, Masayuki; Wada, Tatsuo; Sasabe, Hiroyuki, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 255, p. 113 - 120

  摘要：

  DOI：
• 作为产物：
  描述：

  乙二醇 、 氰乙酸甲酯 在 tetrabutoxytitanium 作用下， 反应 12.0h， 以71%的产率得到cyanoacetic acid 2-(2-cyanoacetoxy) ethyl ester
  参考文献：
  名称：

  Small Molecule Inhibitors of Dynamin I GTPase Activity:  Development of Dimeric Tyrphostins

  摘要：

  Dynamin I is a GTPase enzyme required for endocytosis and is an excellent target for the design of potential endocytosis inhibitors. Screening of a library of tyrphostins, in our laboratory, against the GTPase activity of dynamin I gave rise to a mu M potent lead, 2-cyano-3-(3,4-dihydroxyphenyl)thioacrylamide (1, IC50 70 mu M). Our initial investigations suggested that only the dimeric form of 1 displayed dynamin I GTPase inhibitory activity. Subsequent synthetic iterations were based on dimeric analogues and afforded a number of small molecules, low mu M potent, inhibitors of dynamin I GTPase, in particular, symmetrical analogues with a minimum of two free phenolic -OHs: catechol-acrylamide (9) (IC50 = 5.1 +/- 0.6 mu M), its 3,4,5-trihydroxy congener (10) (IC50 = 1.7 +/- 0.2 mu M), and the corresponding 3-methyl ether (11) (IC50 = 9 3 mu M). Increasing the length of the central alkyl spacer from ethyl to propyl (22-24) afforded essentially identical activity with IC50'S of 1.7 0.2, 1.7 0.2, and 5 +/- 1 mu M, respectively. No decrease in activity was noted until the introduction of a hexyl spacer. Our studies highlight the requirement for two free amido NHs with neither the mono-N-methyl (86) nor the bis-N-methyl (87) analogues inhibiting dynamin I GTPase. A similar effect was noted for the removal of the nitrile moieties. However, modest potency was observed with the corresponding ester analogues of 9-11: ethyl ester (90), propyl ester (91), and butyl ester (92), with IC50'S of 42 3, 38 2, and 61 2 mu M, respectively. Our studies reveal the most potent and promising dynamin I GTPase inhibitor in this series as (22), which is also known as BisT.

  DOI：

  10.1021/jm040208l

文献信息

• Reactions of isocyanates with compounds containing active methylene groups in the presence of triethylamine
  作者：Yu. G. Gololobov、O. A. Linchenko、I. R. Golding、M. A. Galkina、I. Yu. Krasnova、I. A. Garbuzova、P. V. Petrovskii

  DOI：10.1007/s11172-006-0129-y

  日期：2005.10

  Compounds containing active methylene groups react with isocyanates of different structures in the presence of triethylamine to form functionally substituted amides.

  含有活性亚甲基的化合物在三乙胺存在下与不同结构的异氰酸酯反应形成官能取代的酰胺。
• Room Temperature Dynamic Polymers Based on Diels-Alder Chemistry
  作者：P. Reutenauer、E. Buhler、P. J. Boul、S. J. Candau、J.-M. Lehn

  DOI：10.1002/chem.200802145

  日期：2009.2.9

  Polymer, heal thyself! Dynamic polymers formed by a reversible Diels–Alder reaction were formed and studied by using neutron scattering at room temperature. They were used to obtain thin films that displayed self‐healing at room temperature (see figure).

  聚合物，治愈自己！由可逆的狄尔斯-阿尔德反应形成的动态聚合物是通过在室温下使用中子散射来形成和研究的。它们被用来获得在室温下表现出自愈性的薄膜（见图）。
• US2426056
  申请人：——

  公开号：——

  公开（公告）日：——
• RADIOGRAPHIC ELEMENT
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0555465A1

  公开（公告）日：1993-08-18
• LIGHT-ABSORBING POLYMERS
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0588962A1

  公开（公告）日：1994-03-30