cyanoacetate | 23297-32-7

• 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: cyanoacetate
• 英文别名: cyanoacetic acid; deprotonated form；Cyanoacetat；2-cyanoacetate
• CAS: 23297-32-7
• 化学式: C₃H₂NO₂
• 分子量: 84.0544
• InChiKey: MLIREBYILWEBDM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyanoacetate 在 tungsten(pentacarbonyl)(cyanoacetic acid) 作用下， 以 乙二醇二甲醚 为溶剂， 生成 氰乙酸 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The catalytic decarboxylation of cyanoacetic acid: anionic tungsten carboxylates as homogeneous catalysts

  摘要：

  Cyanoacetic acid was observed to catalytically decompose to its component parts, CO2 and CH3CN, in the presence of soluble tungsten(0) carboxylates. In the case in which W(CO)5O2CCH2CN was used as the catalyst, the reaction was inhibited by the substrate via an equilibrium process in which the free acid displaced the carboxylate ligand and bound to the metal through the nitrogen atom. The equilibrium constant for this process was measured and determined to be 0.413 at 50-degrees-C, where k(f) = 6.11 x 10(-3) M-1 s-1 and k(r) = 1.48 x 10 2 M-1 s-1. Activation parameters for the decarboxylation process were determined and yielded DELTAH* = 21.0 +/- 0.7 kcal.mol-1 and DELTAS* = -3.4 +/- 1.9 eu. The rate limiting step is proposed to be loss of cis CO from the metal with concomitant formation of cis-W(CO)4(O2CCH2CN)(NCCH2COOH)-, since the free energy of activation is quite similar to that for cis carbonyl loss, 23.0 +/- 0.9 kcal.mol-1. Subsequent proton transfer and CO2 loss are fast relative to cis CO displacement. The carboxylate ligand acts as an intramolecular Lewis base, mediating the proton-transfer steps. This was demonstrated by the use of W(CO)PPh2(CH2)nX (n = 1 or 2, X = base) as catalysts for the same decarboxylation. Detailed kinetic studies and a proposed mechanism are presented.

  DOI：

  10.1021/ja00064a031
• 作为产物：
  描述：

  (E)-2-氰基-3-(4-甲氧基苯基)丙烯酸 在 氢氧化钾 、 potassium chloride 作用下， 以 水 、 乙腈 为溶剂， 生成 cyanoacetate 、 4-甲氧基苯甲醛
  参考文献：
  名称：

  Extended ElcB mechanism for ester hydrolysis: allylic substitution via carbanion in ester hydrolysis

  摘要：

  DOI：

  10.1021/ja00370a033
• 作为试剂：
  描述：

  在 cyanoacetate 、 sodium chloride 作用下， 以 水 为溶剂， 生成 2-苯基-1-(噻吩-2-基)乙酮
  参考文献：
  名称：

  Keto–enol interconversion of 2-phenylacetylthiophene

  摘要：

  通过结合烯醇化和酮化的速率常数，确定 2-苯乙酰基噻吩（2PAT）的酮烯醇同分异构平衡常数 KTÂ =Â [enol]/[ketone] 为 3.55Â Â 10â7 (pKT 6.45)。分光光度法测得 2PAT 电离的 pKaKH 为 14.60。将其与 pKT 相结合，得出 2PAT 烯醇形式的 pKaEH 为 8.15。将这些值与之前报道的 2-苯乙酰基呋喃和脱氧苯偶姻的值进行比较，结果表明这两个五元杂环（a）在增加烯醇的酸度方面，以及（b）在稳定酮体而不是烯醇同系物方面，都有显著的影响。阳离子表面活性剂（CTABr）产生的胶束会大大降低 2PAT 对映体的酮化速率，并增加酮形式的表观酸度。

  DOI：

  10.1039/a702589k

文献信息

• 6-O-Substituted Benzoxazole and Benzothiazole Compounds and Methods of Inhibiting CSF-1R Signaling
  申请人：Sutton James C.

  公开号：US20120225861A1

  公开（公告）日：2012-09-06

  Benzoxazole and benzothiazole compounds and the stereoisomers, tautomers, solvates, oxides, esters, and prodrugs thereof and pharmaceutically acceptable salts thereof are disclosed. Compositions of the compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier, and uses of the compounds, either alone or in combination with at least one additional therapeutic agent are also disclosed. The embodiments are useful for inhibiting cellular proliferation, inhibiting the growth and/or metathesis of tumors, treating or preventing cancer, treating or preventing degenerating bone diseases such as rheumatoid arthritis, and/or inhibiting molecules such as CSF-1R.

  公开了苯并噻唑化合物和苯并噻唑类化合物的立体异构体、互变异构体、溶剂化物、氧化物、酯和前药及其药学上可接受的盐。还公开了这些化合物的组合物，其可以与至少一种额外的治疗剂一起使用，并与药学上可接受的载体结合使用。这些实施例对于抑制细胞增殖、抑制肿瘤的生长和/或代谢、治疗或预防癌症、治疗或预防退化性骨疾病如类风湿性关节炎以及/或抑制CSF-1R等分子具有用途。
• 6-O-SUBSTITUTED BENZOXAZOLE AND BENZOTHIAZOLE COMPOUNDS AND METHODS OF INHIBITING CSF-1R SIGNALING
  申请人：Sutton C James

  公开号：US20080045528A1

  公开（公告）日：2008-02-21

  Benzoxazole and benzothiazole compounds and the stereoisomers, tautomers, solvates, oxides, esters, and prodrugs thereof and pharmaceutically acceptable salts thereof are disclosed. Compositions of the compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier, and uses of the compounds, either alone or in combination with at least one additional therapeutic agent are also disclosed. The embodiments are useful for inhibiting cellular proliferation, inhibiting the growth and/or metathesis of tumors, treating or preventing cancer, treating or preventing degenerating bone diseases such as rheumatoid arthritis, and/or inhibiting molecules such as CSF-1R.

  本发明涉及苯并噁唑和苯并噻唑化合物及其立体异构体、互变异构体、溶剂化物、氧化物、酯类和前药，以及其药学上可接受的盐。还披露了化合物的组合物，其可以单独使用或与至少一种其他治疗剂联合使用，与药学上可接受的载体相结合，并且披露了化合物的用途，可以单独使用或与至少一种其他治疗剂联合使用。所述实施例有助于抑制细胞增殖，抑制肿瘤的生长和/或代谢，治疗或预防癌症，治疗或预防退变性骨疾病，例如类风湿性关节炎，以及/或抑制分子如CSF-1R。
• Higher alkyl esters of cyanoacetic acid
  申请人：Creanova Inc.

  公开号：US06271410B1

  公开（公告）日：2001-08-07

  C3-12 alkyl, substituted alkyl, alkenyl and cycloalkyl cyanoacetates are prepared by an efficient and simplified one-step process in which a small molar excess of the corresponding alcohol, i.e., C3-12 alkyl, substituted alkyl, alkenyl or cycloalkenyl alcohol is reacted with crystalline cyanoacetic acid, or a concentrated aqueous solution of cyanoacetic acid, in the presence of an acid catalyst, such as, for example, methanesulfonic acid, p-toluenesulfonic acid, sulfuric acid and phosphoric acid at a temperature in the range of from about 60° C. to about 150° C., in accordance with the following reaction: CNCH2COOH+R—OH→(cat)CNCH2COOR+H2O  (I) where R is a C3-12 alkyl, substituted alkyl, alkenyl or cycloalkyl.

  C3-12烷基，取代烷基，烯基和环烷基的氰乙酸酯可以通过高效而简化的一步法制备，其中与结晶的氰乙酸或浓缩的氰乙酸水溶液在酸催化剂（例如甲磺酸，对甲苯磺酸，硫酸和磷酸）的存在下反应，反应温度在约60℃至约150℃的范围内，反应方程式如下: CNCH2COOH + R-OH →（催化剂）CNCH2COOR + H2O（I），其中R是C3-12烷基，取代烷基，烯基或环烷基。
• N-oxides of amino containing pyrido \x9b2,3-D! pyrimidines
  申请人：Warner-Lambert Company

  公开号：US05945422A1

  公开（公告）日：1999-08-31

  N-oxides of amino containing 6-aryl pyrido\x9b2,3-d!-pyrimidine 7-imines, 7-ones, and 7-thiones have the formula ##STR1## where A and B are linkers, Ar is aryl, R.sub.2 is aklyl, X is O, S, or NH, or NAcyl, and R.sub.5 and R.sub.6 are alkyl. The compounds are inhibitors of protein tyrosine kinases and cyclin-dependent kinases, and are thus useful in treating cellular proliferation mediated thereby. The compounds are especially useful in treating cancer, atherosclerosis, restenosis, and psoriasis.

  含有6-芳基吡啶\x9b2,3-d!-嘧啶7-亚胺、7-酮和7-硫酮的N-氧化物的化学式为##STR1## 其中A和B是连接剂，Ar是芳基，R.sub.2是烷基，X是O、S、NH或NAcyl，R.sub.5和R.sub.6是烷基。这些化合物是蛋白酪氨酸激酶和细胞周期依赖性激酶的抑制剂，因此可用于治疗由此介导的细胞增殖。这些化合物在治疗癌症、动脉粥样硬化、再狭窄和牛皮癣方面特别有用。
• 6-O-substituted benzoxazole and benzothiazole compounds and methods of inhibiting CSF-1R signaling
  申请人：Sutton James C.

  公开号：US20100280006A1

  公开（公告）日：2010-11-04

  Benzoxazole and benzothiazole compounds and the stereoisomers, tautomers, solvates, oxides, esters, and prodrugs thereof and pharmaceutically acceptable salts thereof are disclosed. Compositions of the compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier, and uses of the compounds, either alone or in combination with at least one additional therapeutic agent are also disclosed. The embodiments are useful for inhibiting cellular proliferation, inhibiting the growth and/or metathesis of tumors, treating or preventing cancer, treating or preventing degenerating bone diseases such as rheumatoid arthritis, and/or inhibiting molecules such as CSF-1R.

  本文披露了苯并噁唑和苯并噻唑化合物及其立体异构体、互变异构体、溶剂化物、氧化物、酯类和前药，以及其药学上可接受的盐。本文还披露了这些化合物的组合物，可以单独使用或与至少一种其他治疗剂联合使用，并与药学上可接受的载体一起使用，以及这些化合物的用途，可以单独使用或与至少一种其他治疗剂联合使用。这些实施例可用于抑制细胞增殖，抑制肿瘤的生长和/或代谢，治疗或预防癌症，治疗或预防退化性骨病，如类风湿性关节炎，和/或抑制分子，如CSF-1R。