1-(dimethoxymethyl)-2-((4-methoxyphenyl)ethynyl)benzene

• 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: 1-(dimethoxymethyl)-2-((4-methoxyphenyl)ethynyl)benzene
• 英文别名: 1-(Dimethoxymethyl)-2-[2-(4-methoxyphenyl)ethynyl]benzene；1-(dimethoxymethyl)-2-[2-(4-methoxyphenyl)ethynyl]benzene
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: APZINHJTJQJEQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(dimethoxymethyl)-2-((4-methoxyphenyl)ethynyl)benzene 在 C₃₂H₃₆AgN₄O₄S₂⁽¹⁺⁾*BF₄^(1-) 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 78.0h， 生成 1-isopropoxy-3-(4-methoxyphenyl)-1H-isochromene
  参考文献：
  名称：

  Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes

  摘要：

  The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(1) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth H-1 NMR experiments and an aimed "trapping" experiment.

  DOI：

  10.1021/jo5002559
• 作为产物：
  描述：

  邻溴苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 tetra-N-butylammonium tribromide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 1-(dimethoxymethyl)-2-((4-methoxyphenyl)ethynyl)benzene
  参考文献：
  名称：

  金催化的2-炔醛环状缩醛的氢化物转移合成茚满酮衍生物。

  摘要：

  已经开发了一种高效的金催化的2-炔醛环状缩醛的环化反应，用于合成茚满酮衍生物。可以以优良的产率获得各种各样的官能化茚满酮衍生物。HMBC和NOESY NMR分析和机理阐明实验表明，环化是通过1,5-H移位发生的。环状缩醛基团通过激活苄基CH键并通过束缚两个烷氧基基团防止烷氧基基团的迁移来促进1,5-H移位。

  DOI：

  10.1021/acs.orglett.0c00221

文献信息

• Copper Catalyzed Enantioselective Alkylation of Pyrrole with β,γ-Unsaturated α-Ketoesters: Application to One-Pot Construction of the Seven-Membered Ring by Merging a Gold Catalysis
  作者：Yanbin Hu、Yanan Li、Sheng Zhang、Chong Li、Lijun Li、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.orglett.5b01917

  日期：2015.8.21

  A highly enantioselective Friedel Crafts alkylation of pyrrole to beta,gamma-unsaturated alpha-ketoesters was developed by virtue of a chiral copper complex, affording the alkylated derivatives of pyrrole with good yields and excellent enantioselectivities. Moreover, merging copper catalysis with gold catalysis realized a one-pot construction of the seven-membered ring to give annulated pyrroles with moderate to good yields and high enantiomeric excesses.
• Stepwise Delivery of Two Methoxy Groups of Arylaldehyde Acetals across the Phenyl Ring. Vacant Site-Controlled Palladium Catalysis
  作者：Itaru Nakamura、Yuya Mizushima、Ilya D. Gridnev、Yoshinori Yamamoto

  DOI：10.1021/ja051114j

  日期：2005.7.13

  A new catalytic cyclization of o-alkynylbenzaidehyde acetals 1 to the functionalized indenes 2 was found to be strictly controlled by the number of triphenylphosphine ligands on the Pd catalyst. Only complexes with three available coordination sites on Pd catalyze this reaction. Mechanistic study suggests that pi-coordination of Pd to the benzene ring is a key step controlled by the number of vacant coordination sites.
• Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives
  作者：Tsuyoshi Yamada、Kwihwan Park、Takumu Tachikawa、Akiko Fujii、Matthias Rudolph、A. Stephen K. Hashmi、Hironao Sajiki

  DOI：10.1021/acs.orglett.0c00221

  日期：2020.3.6

  An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H

  已经开发了一种高效的金催化的2-炔醛环状缩醛的环化反应，用于合成茚满酮衍生物。可以以优良的产率获得各种各样的官能化茚满酮衍生物。HMBC和NOESY NMR分析和机理阐明实验表明，环化是通过1,5-H移位发生的。环状缩醛基团通过激活苄基CH键并通过束缚两个烷氧基基团防止烷氧基基团的迁移来促进1,5-H移位。
• Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes
  作者：Monica Dell’Acqua、Brunilde Castano、Clara Cecchini、Tommaso Pedrazzini、Valentina Pirovano、Elisabetta Rossi、Alessandro Caselli、Giorgio Abbiati

  DOI：10.1021/jo5002559

  日期：2014.4.18

  The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(1) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth H-1 NMR experiments and an aimed "trapping" experiment.