2-nonen-4-ynoic acid | 74177-08-5

• 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: 2-nonen-4-ynoic acid
• 英文别名: (E)-2-nonen-4-ynoic acid；(E)-non-2-en-4-ynoic acid；non-2t-en-4-ynoic acid；Non-2t-en-4-insaeure
• CAS: 74177-08-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: DXTAOHVZICGRNW-BQYQJAHWSA-N

物化性质

• 熔点：
  45 °C
• 沸点：
  262.1±23.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-nonen-4-ynoic acid 在 吡啶 、 草酰氯 、 thallium (I) ethoxide 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 norethisterone (E)-non-2-en-4-ynoate
  参考文献：
  名称：

  Long-acting contraceptive agents: Norethisterone esters of polyunsaturated acids

  摘要：

  Some new derivatives of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) are described in which the 17 beta-hydroxyl group of the steroid is esterified with polyunsaturated aliphatic acids. The potential of these compounds as long-acting contraceptive agents has been evaluated.

  DOI：

  10.1016/0039-128x(83)90098-3
• 作为产物：
  描述：

  ethyl (E)-2-nonen-4-ynoate 生成 2-nonen-4-ynoic acid
  参考文献：
  名称：

  Petragnani; Brocksom; Gato, Farmaco, Edizione Scientifica, 1977, vol. 32, # 9, p. 627 - 634

  摘要：

  DOI：

文献信息

• Efficient Synthesis of Conjugated (2E)- or (2Z)-En-4-ynoic Acids and (2E,4E)- or (2Z,4E)-Dienoic Acids via Palladium-Catalysed Cross Coupling
  作者：Mohamed Abarbri、Jean-Luc Parrain、Jean-Christophe Cintrat、Alain Duchêne

  DOI：10.1055/s-1996-4171

  日期：1996.1

  (E)- or (Z)-Enynoic acids and (2E,4E)- or (2Z,4E)-dienoic acids can be obtained in good yields under mild conditions through palladium-catalysed cross coupling of (E)- or (Z)-3-iodoprop-2-enoic acid with alkynylzinc or vinyltin reagents.

  (E)-或(Z)-烯炔酸以及(2E,4E)-或(2Z,4E)-二烯酸可以在温和条件下通过钯催化的交叉偶联反应，从(E)-或(Z)-3-碘丙-2-烯酸与炔基锌或乙烯基锡试剂获得，产率良好。
• Stereodivergent Synthesis of (<i>E</i>)- and (<i>Z</i>)-2-Alken-4-yn-1-ols from 2-Propynoic Acid:  A Practical Route via 2-Alken-4-ynoates
  作者：Ryo Takeuchi、Keisuke Tanabe、Shigeru Tanaka

  DOI：10.1021/jo991350a

  日期：2000.3.1
• Long-acting contraceptive agents: Levonorgestrel esters of unsaturated acids
  作者：A.S.C. Wan、T.L. Ngiam、S.L. Leung、M.L. Go、C.G. Francisco、R. Freire、R. Hernandez、J.A. Salazar、E. Suarez、G.A. Garcia、O. Jimeno、J.A.Noguez A.、A.Acosta H.、R. Vlahov、V. Tarpanov、M. Boshkova-Ljapova、B. Milenkov、V. Stoilova、J. Vlahov、G. Snatzke

  DOI：10.1016/0039-128x(83)90105-8

  日期：1983.3

  Esters of levonorgestrel (13 beta-ethyl-17 beta-ethynyl-17 beta-hydroxygon-4-en-3-one) with a variety of unsaturated carboxylic acids have been synthesized for evaluation as potential long-acting, injectable contraceptive agents.
• Julia; Bullot, Bulletin de la Societe Chimique de France, 1959, p. 1828,1832
  作者：Julia、Bullot

  DOI：——

  日期：——
• A short synthesis of conjugated unsaturated alcohols
  作者：Uli Kazmaier

  DOI：10.1016/s0040-4020(97)10385-4

  日期：1998.2

  Isomerization of acetylenic pentafluorophenyl esters in the presence of phosphines gives rise to activated dienoic esters, which can be reduced directly in a simple one pot procedure to the corresponding conjugated unsaturated alcohols 6-10. The higher reactivity of the pentafluorophenyl esters in comparison to alkyl esters allows their selective isomerization. (C) 1998 Elsevier Science Ltd. All rights reserved.