2-[hydroxy(3-methoxy-phenyl)methyl]buta-2,3-dienoic acid ethyl ester | 1041333-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[hydroxy(3-methoxy-phenyl)methyl]buta-2,3-dienoic acid ethyl ester
• CAS: 1041333-46-3
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: XNIZQEXUFNHZPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[hydroxy(3-methoxy-phenyl)methyl]buta-2,3-dienoic acid ethyl ester 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到
  参考文献：
  名称：

  Efficient Synthetic Method of Z-Selective 2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide

  摘要：

  在 $CH_2Cl_2$ 中，具有乙氧羰基和乙烯基的烯醇与三卤化铟在室温下发生反应，从而开发出一种高效的 Z 选择性 3-乙氧羰基-2-卤-1,3-二烯和 3-乙烯基-2-卤-1,3-二烯的合成方法。

  DOI：

  10.5012/bkcs.2010.31.03.645
• 作为产物：
  描述：

  ethyl 4-bromobut-2-ynoate 、 3-甲氧基苯甲醛 在 indium 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[hydroxy(3-methoxy-phenyl)methyl]buta-2,3-dienoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective DABCO-Catalyzed Synthesis of (E)-α-Ethynyl-α,β-Unsaturated Esters from Allenyl Acetates

  摘要：

  (E)-α-炔基-α,β-不饱和酯从艾林基甲酯用10摩尔% DABCO在DMF常温下处理可得到优良收率。

  DOI：

  10.1021/ol9001703

文献信息

• Synthesis of (E)-α-Ethynyl-α,β-unsaturated Esters from Allenyl Acetates Catalyzed by DABCO and Their Application to Sonogashira Cross-Coupling Reactions
  作者：Hyun-Seok Kim、Doo-Sup Shin、Kwang-Moo Lee、Sang-Kyu Lee、Sang-Hyuk Kim、Phil-Ho Lee

  DOI：10.5012/bkcs.2010.31.03.742

  日期：2010.3.20

  esters from another precursor without the use of (Z)-α-halo-α,β-unsaturated esters. As part of our continuing studies into the utility of allene groups, we report herein the preparation of the selective synthesis of (E)-α-ethynyl-α,β-unsaturated esters from allenyl acetates catalyzed by DABCO and their application to Sonogashira cross-coupling reaction (Scheme 1). First, various allenyl acetates were

  1 PPTS (0.2) CH2Cl2 6 0 2 AcOH (0.2) DMF 12 0 3 吡啶 (0.2) DMF 0.67 75 4 PPh3 (0.2) DMF 0.5 69 5 DABCO (0.2) DMF 0.5 75 6 DABCO (0.2) THF 4.5 50 7 DABCO (0.2) CH3CN 4.5 70 8 DABCO (0.1) DMF 2.5 81 由于 α-乙炔基-α,β-不饱和酯的合成是有机合成化学中具有挑战性的问题之一，许多有效的合成方法已被用于制备这些化合物。报道。然而，仍然需要一种高选择性的 (E)-α-乙炔基-α,β-不饱和酯合成方法。通常，这些化合物的选择性合成是通过过渡金属催化的(Z)-α-卤代-α,β-不饱和酯与末端炔烃的交叉偶联反应通过Sonogashira交叉偶联反应完成的。然而，该方法受到限制，因为 (Z)-α-halo-α 的
• Stereoselective DABCO-Catalyzed Synthesis of (<i>E</i>)-α-Ethynyl-α,β-Unsaturated Esters from Allenyl Acetates
  作者：Yongsik Choe、Phil Ho Lee

  DOI：10.1021/ol9001703

  日期：2009.3.19

  (E)-alpha-Ethynyl-alpha,beta-unsaturated esters were exclusively prepared in good to excellent yields from treatment of allenyl acetates with 10 mol % DABCO in DMF at room temperature.

  (E)-α-炔基-α,β-不饱和酯从艾林基甲酯用10摩尔% DABCO在DMF常温下处理可得到优良收率。
• Indium-Mediated Regio- and Chemoselective Synthesis of α-Hydroxyalkyl Allenic Esters and Gold-Catalyzed Cyclizations to Ethyl 2-Naphthoate Derivatives
  作者：Chansoo Park、Phil Ho Lee

  DOI：10.1021/ol801196g

  日期：2008.8.7

  The regio- and chemoselective synthetic method of functionalized alpha-hydroxyalkyl allenic esters was developed from the reactions of various aldehydes with organoindium reagent generated in situ from indium and ethyl 4-bromobutynoate. The alpha-hydroxyalkyl allenic esters possessing electron-donating groups were cyclized to ethyl 2-naphthoate derivatives through intramolecular C-alkylation catalyzed by gold salts.
• Synthesis of 2-Alkyl- and Aryl-3-ethoxycarbonyl-2,5-dihydrofurans through Gold-Catalyzed Intramolecular Hydroalkoxylation
  作者：Dahan Eom、Dongjin Kang、Phil Ho Lee

  DOI：10.1021/jo101474s

  日期：2010.11.5

  Treatment of a wide range of functionalized hydroxyallenic esters with 5 mol % Ph3PAuCl and 5 mol % AgOTf in CH2Cl2 at 25 degrees C for l h produced selectively 2-alkyl- and aryl-3-ethoxycarbony1-2,5-dihydrofurans in good to excellent yield through intramolecular hydroalkoxylation by a 5-endo mode.
• Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-<i>Endo</i> Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans
  作者：Sanghyuck Kim、Phil Ho Lee

  DOI：10.1021/jo2018125

  日期：2012.1.6

  Ethyl alpha-(1-hydroxy-1-alkyl)methylallenoates and alpha-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the alpha-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbony1-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.