4-phenoxy-but-2-ynoic acid methyl ester | 33313-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-phenoxy-but-2-ynoic acid methyl ester
• 英文别名: Methyl 4-phenoxybut-2-ynoate
• CAS: 33313-70-1
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: TZIMLZGJYGWYRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenoxy-but-2-ynoic acid methyl ester 在 palladium diacetate 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以59%的产率得到2H-chromene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.

  DOI：

  10.1021/ol034177k
• 作为产物：
  描述：

  4-phenoxybut-2-yn-1-ol 在 chromium(VI) oxide 、 硫酸 作用下， 生成 4-phenoxy-but-2-ynoic acid methyl ester
  参考文献：
  名称：

  Besace,Y. et al., Bulletin de la Societe Chimique de France, 1971, p. 2275 - 2279

  摘要：

  DOI：

文献信息

• Ring expansion of substituted norbornadienes for the synthesis of mono- and disubstituted 2-azabicyclo[3.2.1]octadienes
  作者：Nova Emelda、Stephen C. Bergmeier

  DOI：10.1016/j.tetlet.2008.06.123

  日期：2008.9

  substituted 2-azabicyclo[3.2.1]octadiene system via reaction with toluenesulfonyl azide. We have found that both and mono- and disubstituted norbornadienes will undergo the cycloaddition/rearrangement sequence to provide the bicyclooctadiene ring system as a single regioisomer. The 2-azabicyclo[3.2.1]octane ring system can be prepared from the unsaturated 2-azabicyclo[3.2.1]octadiene ring system.

  我们研究了取代的降冰片二烯通过与甲苯磺酰叠氮化物反应转化为取代的 2-氮杂双环 [3.2.1] 辛二烯体系。我们已经发现，单和二取代的降冰片二烯和单取代的降冰片二烯都将经历环加成/重排序列以提供作为单一区域异构体的双环辛二烯环系统。2-氮杂双环[3.2.1]辛烷环系可由不饱和的2-氮杂双环[3.2.1]辛二烯环系制备。
• Facile synthesis of acetylenecarboxylates by the oxidative carbonylation of terminal acetylenes catalyzed by PdCl2 under mild conditions
  作者：Jiro Tsuji、Mitsuo Takahashi、Takashi Takahashi

  DOI：10.1016/s0040-4039(00)71522-x

  日期：1980.1
• Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization
  作者：Stefan J Pastine、So Won Youn、Dalibor Sames

  DOI：10.1016/j.tet.2003.05.003

  日期：2003.11

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.
• TSUGI J.; TAKAHASHI M.; TAKAHASHI T., TETRAHEDRON LETT., 1980, 21, NO 9, 849-850
  作者：TSUGI J.、 TAKAHASHI M.、 TAKAHASHI T.

  DOI：——

  日期：——
• URALOV A. U.; ABIDOV U. A.; MAXSUMOV A. G., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 29,(1986) N 12, 111-112
  作者：URALOV A. U.、 ABIDOV U. A.、 MAXSUMOV A. G.

  DOI：——

  日期：——