3-Butylamino-cis-crotonsaeure-ethylester | 21759-73-9

• 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: 3-Butylamino-cis-crotonsaeure-ethylester
• 英文别名: ethyl (E)-3-(butylamino)but-2-enoate
• CAS: 21759-73-9
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: IFKSUXQHAOSFCH-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Butylamino-cis-crotonsaeure-ethylester 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 1-butyl-4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones

  摘要：

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.

  DOI：

  10.1016/0223-5234(91)90194-r
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 正丁胺 在 ammonium cerium(IV) nitrate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以98%的产率得到3-Butylamino-cis-crotonsaeure-ethylester
  参考文献：
  名称：

  General, Mild and Efficient Synthesis of β-Enaminones Catalyzed by Ceric Ammonium Nitrate

  摘要：

  铈铵硝酸盐催化芳香族或脂肪族初级胺与多种β-二羰基化合物的反应，包括β-酮酯、β-酮硫酯和β-二酮。该反应在室温下顺利进行，反应时间短，产物为β-烯酰胺，产率良好至优异。

  DOI：

  10.1055/s-2007-973862

文献信息

• Reaction of β-enaminones and acetylene dicarboxylates: synthesis of substituted 1,2-dihydropyridinones
  作者：Vemu Nagaraju、Dalovai Purnachander、N. S. V. M. Rao Mangina、Surisetti Suresh、Balasubramanian Sridhar、Galla V. Karunakar

  DOI：10.1039/c4ob01578a

  日期：——

  Synthesis of substituted 1,2-dihydropyridinones is described in a one pot reaction of β-enaminones and acetylene dicarboxylates where new C–C and C–N bonds were formed. The title compounds were obtained in moderate to good yields.

  β-烯胺酮与乙炔二羧酸酯的一锅反应中描述了取代的1,2-二氢吡啶酮的合成，其中形成了新的C–C和C–N键。以中等至良好的产率获得标题化合物。
• Benzannulation and <i>N</i> ‐Annulation of β‐Ketoenamines for Synthesizing Aniline and Pyridine Derivatives Using DMSO as a Methine Source
  作者：Pallaba Ganjan Dalai、Niranjan Panda

  DOI：10.1002/adsc.202200886

  日期：2022.11.8

  N-annulation of β-ketoenamines by the in-situ generated methyl(methylene)sulfonium ion from the reaction of dimethyl sulfoxide (DMSO) and 1,2-dibromoethane (DBE) was achieved. The β-ketoenamines underwent N-annulation to pyridine derivatives, while the N-alkylated enamines were benzannulated to afford substituted anilines. The utility of the intermediate methyl(methylene)sulfonium ion was further extended for

  通过二甲基亚砜（DMSO）和1,2-二溴乙烷（DBE）的反应原位产生的甲基（亚甲基）锍离子实现了β-酮烯胺的苯环化和N-环化。β-酮烯胺经 N-环化生成吡啶衍生物，而N-烷基化烯胺经苯环化生成取代的苯胺。中间体甲基（亚甲基）锍离子的用途进一步扩展用于合成亚甲基桥联双-1,3-二羰基化合物。
• Aza-annulation of enaminones with crotonyl chloride — Formal reversal of regioselectivity
  作者：James P. Murphy、Mark Hadden、Paul J. Stevenson

  DOI：10.1016/s0040-4020(97)00755-2

  日期：1997.8

  The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.
• IKCa-channel blockers. Part 2: Discovery of cyclohexadienes
  作者：Klaus Urbahns、Siegfried Goldmann、Jochen Krüger、Ervin Horváth、Joachim Schuhmacher、Rolf Grosser、Volker Hinz、Frank Mauler

  DOI：10.1016/j.bmcl.2004.10.063

  日期：2005.1

  Novel cyclohexadienes have been identified as potent and specific IKCa-channel blockers. In this communication we describe their synthesis as well as their chemical and biological properties. A selected derivative is being enriched in rat brain and reduces the infarct volume, intracranial pressure as well as the water content in a rat subdural hematoma model of traumatic brain injury after iv administration. (C) 2004 Elsevier Ltd. All rights reserved.
• GOLDMANN, S.;SCHRAMM, M.;THOMAS, G.;GROSS, R.
  作者：GOLDMANN, S.、SCHRAMM, M.、THOMAS, G.、GROSS, R.

  DOI：——

  日期：——