2-[(3,5-dimethoxyphenyl)hydroxymethyl]buta-2,3-dienoic acid ethyl ester | 1041333-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(3,5-dimethoxyphenyl)hydroxymethyl]buta-2,3-dienoic acid ethyl ester
• CAS: 1041333-50-9
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: ODWXFYIPPMLYQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(3,5-dimethoxyphenyl)hydroxymethyl]buta-2,3-dienoic acid ethyl ester 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到ethyl 5,7-dimethoxy-2-naphthoate
  参考文献：
  名称：

  Indium-Mediated Regio- and Chemoselective Synthesis of α-Hydroxyalkyl Allenic Esters and Gold-Catalyzed Cyclizations to Ethyl 2-Naphthoate Derivatives

  摘要：

  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.

  DOI：

  10.1021/ol801196g
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 ethyl 4-bromobut-2-ynoate 在 indium 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(3,5-dimethoxyphenyl)hydroxymethyl]buta-2,3-dienoic acid ethyl ester
  参考文献：
  名称：

  DABCO催化乙酸烯丙酯合成(E)-α-乙炔基-α,β-不饱和酯及其在Sonogashira交叉偶联反应中的应用

  摘要：

  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

  DOI：

  10.5012/bkcs.2010.31.03.742

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。
• 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.
• Copper(I)‐catalyzed Cyclization Reactions of Ethyl ( <i>E</i> )‐α‐Ethynyl‐β‐Aryl‐α,β‐Unsaturated Esters with <i>N</i> ‐Sulfonyl Azides: Synthesis of 1‐Aminonaphthalene, 3‐Aminobenzofuran, and 3‐Aminothiobenzofuran Derivatives
  作者：Jeong‐Yu Son、Gi Uk Han、Gi Hoon Ko、Chanyoung Maeng、Seohyun Shin、Phil Ho Lee

  DOI：10.1002/bkcs.11755

  日期：2019.7

  4‐(alkyl or arylsulfonamido)‐2‐naphthoates from ethyl (E)‐α‐ethynyl‐β‐aryl‐α,β‐unsaturated esters (1) and N‐sulfonyl azides (2) in the presence of 2,6‐lutidine in THF at 60 °C for 3 h was developed in one step, in which a copper(I)‐catalyzed 1,3‐dipolar cycloaddition, ketenimine formation, and 6π‐electrocyclization followed by [1,3]‐H shift tandem reaction took place. This method enabled efficient synthesis

  在存在条件下由乙基（E）-α-乙炔基-β-芳基-α，β-不饱和酯（1）和N-磺酰基叠氮化物（2）合成4-（烷基或芳基磺酰胺基）-2-萘甲酸乙酯的合成方法一步制得了60℃下3,6,6-二甲基吡啶在THF中3小时，其中铜（I）催化1,3-偶极环加成，烯酮亚胺形成和6π-电环化，然后进行[1,3 ] -H移位串联反应发生。这种方法可以在释放分子氮的情况下有效合成各种1-氨基萘和3-氨基苯并呋喃以及3-氨基苯并噻吩衍生物。
• 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.