2-丙炔酸,3-(2-羟基苯基)- | 16635-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-丙炔酸,3-(2-羟基苯基)-
• 英文名称: 3-(2-hydroxyphenyl)propynoic acid
• 英文别名: (2-hydroxyphenyl)propynoic acid；o-Hydroxy-phenyl-propiolsaeure；o-Hydroxy-phenylpropiolsaeure；o-Hydroxyphenyl-propiolsaeure；3-(2-hydroxyphenyl)prop-2-ynoic Acid
• CAS: 16635-92-0
• 化学式: C₉H₆O₃
• 分子量: 162.145
• InChiKey: VYVSCBZOSRUQCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C(Solv: benzene (71-43-2); 1,2-dichloroethane (107-06-2))
• 沸点：
  359.2±34.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丙炔酸,3-(2-羟基苯基)- 在 Lindlar's catalyst 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 (Z)-3-<2-(acetyloxy)phenyl>-2-propenoic acid
  参考文献：
  名称：

  Two new improved approaches to the synthesis of coumarin-based prodrugs

  摘要：

  Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated me clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low overall yield. In this report, we describe two new approaches to the synthesis of these coumarin-based prodrugs. The first approach is a photochemical approach taking advantage of the photoisomerization of cinnamic acid and its derivatives. The second approach is through the catalytic hydrogenation of a triple bond for the generation of me cis double bond in the coumarinic acid moiety. Both approaches allow for the synthesis of these prodrugs in fewer steps with much improved overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00121-0
• 作为产物：
  描述：

  苯并呋喃-2-羧酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到2-丙炔酸,3-(2-羟基苯基)-
  参考文献：
  名称：

  Buttery, Cheryl D.; Knight, David W.; Nott, Andrew P., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2839 - 2843

  摘要：

  DOI：

文献信息

• (Ethoxycarbonyliodomethyl)triphenylphosphonium Iodide: A Convenient Reagent for the Direct Synthesis of β-Substituted Propiolic Acids<i>via</i>the Corresponding Esters
  作者：Jaques Chenault、Jean-François E. Dupin

  DOI：10.1055/s-1987-27983

  日期：——

  Reaction between (ethoxycarbonyliodomethyl)triphenylphosphonium iodide, potassium carbonate, and various aromatic or aliphatic aldehydes in a liquid solid two phases system gives ß-substituted propiolic esters. The corresponding acids are obtained in good yield by hydrolysis.

  （乙氧基羧基碘甲基）三苯基膦碘化物、碳酸钾与各种芳香或脂肪醛在液固两相体系中反应，生成β-取代丙炔酸酯。通过水解可以获得相应的酸，产率良好。
• β-Deprotonation by lithium di-isopropylamide. Vinyl carbanions from oxygen heterocycles in the synthesis of carboxylic acids in the benzofuran, flavone, and coumarin series and in the regiospecific acylation of 2,6-dimethylchromone
  作者：Ana M. B. S. R. C. S. Costa、Francis M. Dean、Michael A. Jones、Dennis A. Smith、Rajender S. Varma

  DOI：10.1039/c39800001224

  日期：——

  Lithium di-isopropylamide at –70 °C can remove the α-proton from benzofuran in the absence of activating groups and the β-proton if such groups are present; in flavone and 4-methoxycoumarin β-deprotonation occurs readily and the carbanions are easily carboxylated giving acids not previously accessible, while in 2,6-dimethylchromone β-deprotonation is kinetically favoured allowing 3-acylation to be

  在不存在活化基团的情况下，–70°C的二异丙基氨基化锂可从苯并呋喃中去除α-质子；如果存在此类基团，则可去除β-质子；黄酮和4-甲氧基香豆素中的β-去质子化很容易发生，碳负离子容易被羧化，产生以前无法获得的酸，而2,6-二甲基色酮中β-去质子化在动力学上是有利的，从而使3-酰化与传统的酰化反应分开进行。 2-甲基。
• Rhodium-catalyzed enantio- and diastereoselective intramolecular [2 + 2 + 2] cycloaddition of unsymmetrical dienynes
  作者：Hiromi Sagae、Keiichi Noguchi、Masao Hirano、Ken Tanaka

  DOI：10.1039/b804294b

  日期：——

  A cationic rhodium(I)/(R)-H8-BINAP or (R)-Segphos complex catalyzes an intramolecular [2 + 2 + 2] cycloaddition of unsymmetrical dienynes, leading to fused tri- and tetracyclic cyclohexenes bearing two tertiary or quaternary carbon centers in high yields with high enantio- and diastereoselectivity.

  阳离子铑（I）/(R)-H8-BINAP 或 (R)-Segphos 复合物可催化不对称二炔的分子内[2 + 2 + 2]环加成反应，从而高产率、高对映和非对映选择性地生成含有两个三级或四级碳中心的融合三环和四环环己烯。
• Buttery, Cheryl D.; Knight, David W.; Nott, Andrew P., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2839 - 2843
  作者：Buttery, Cheryl D.、Knight, David W.、Nott, Andrew P.

  DOI：——

  日期：——
• Methods for the homologation of benzofurancarboxylic acids using dianionic intermediates
  作者：Cheryl D. Buttery、David W. Knight、Andrew P. Nott

  DOI：10.1016/s0040-4039(00)88366-5

  日期：1982.1