3-(2-乙酰氧基苯基)丙-2-炔酸 | 61547-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 3-(2-乙酰氧基苯基)丙-2-炔酸
• 英文名称: 3-(2-acetyloxyphenyl)propynoic acid
• 英文别名: o-Acetoxy-phenylpropiolsaeure；3-[2-(Acetyloxy)phenyl]prop-2-ynoic acid；3-(2-acetyloxyphenyl)prop-2-ynoic acid
• CAS: 61547-40-8
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: VNTTUKKQHLADDG-UHFFFAOYSA-N

物化性质

• 熔点：
  109 °C (decomp)
• 沸点：
  382.8±34.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-乙酰氧基苯基)丙-2-炔酸 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到(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 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.17h， 生成 3-(2-乙酰氧基苯基)丙-2-炔酸
  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

文献信息

• BABIN P.; BOURGEOIS P.; DUNOGUES J., C. R. ACAD. SCI. <CHDC-AQ>, 1976, C 283, NO 4, 149-152
  作者：BABIN P.、 BOURGEOIS P.、 DUNOGUES J.

  DOI：——

  日期：——
• Two new improved approaches to the synthesis of coumarin-based prodrugs
  作者：Ailian Zheng、Wei Wang、Huijuan Zhang、Binghe Wang

  DOI：10.1016/s0040-4020(99)00121-0

  日期：1999.4

  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.