acetaldehyde ortho-(1-octynyl)phenyl ethyl acetal | 870011-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: acetaldehyde ortho-(1-octynyl)phenyl ethyl acetal
• 英文别名: acetaldehyde ethyl 2-(1-octynyl)phenyl acetal；1-(1-Ethoxyethoxy)-2-oct-1-ynylbenzene；1-(1-ethoxyethoxy)-2-oct-1-ynylbenzene
• CAS: 870011-19-1
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: XZQCNXXSHXMFLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acetaldehyde ortho-(1-octynyl)phenyl ethyl acetal 在 platinum(II) chloride 1,5-cis,cis-cyclooctadiene 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以91%的产率得到3-(1-ethoxyethyl)-2-hexylbenzofuran
  参考文献：
  名称：

  Synthesis of 2,3-disubstituted benzofurans and indoles by π-Lewis acidic transition metal-catalyzed cyclization of ortho-alkynylphenyl O,O- and N,O-acetals

  摘要：

  The PtCl2-catalyzed cyclization reaction of ortho-alkynylphenyl acetals 1 in the presence of COD (1,5-cyclooctadiene) produces 3-(alpha-alkoxyalkyl) benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl) phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl) phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl) phenyl acetal (1f) in the presence of 2 mol% of platinum(II) chloride and 8 mol% of 1,5-cycloocatadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively. Moreover, the reaction of N-methoxymethyl-2-alkynylanilines 3 was catalyzed by PdBr2, affording the corresponding 2,3-disubstituted indoles 4 in moderate yields. For example, the reaction of N-methoxymethyl-2-(1-pentynyl)- N-tosylaniline (3a) and N-methoxymethyl-2-(phenylethynyl)-N-tosylaniline (3b) in the presence of 10 mol% of PdBr2 in toluene at 80 degrees C gave 3-methoxymethyl-2-propyl-1-tosylindole (4a) and 3-methoxymethyl-2-phenyl-1-tosylindole (4b) in 33 and 33% yields, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.039
• 作为产物：
  描述：

  2-碘苯酚 在 palladium dichloride copper(l) iodide 、 4-甲基苯磺酸吡啶 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 acetaldehyde ortho-(1-octynyl)phenyl ethyl acetal
  参考文献：
  名称：

  Synthesis of 2,3-disubstituted benzofurans and indoles by π-Lewis acidic transition metal-catalyzed cyclization of ortho-alkynylphenyl O,O- and N,O-acetals

  摘要：

  The PtCl2-catalyzed cyclization reaction of ortho-alkynylphenyl acetals 1 in the presence of COD (1,5-cyclooctadiene) produces 3-(alpha-alkoxyalkyl) benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl) phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl) phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl) phenyl acetal (1f) in the presence of 2 mol% of platinum(II) chloride and 8 mol% of 1,5-cycloocatadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively. Moreover, the reaction of N-methoxymethyl-2-alkynylanilines 3 was catalyzed by PdBr2, affording the corresponding 2,3-disubstituted indoles 4 in moderate yields. For example, the reaction of N-methoxymethyl-2-(1-pentynyl)- N-tosylaniline (3a) and N-methoxymethyl-2-(phenylethynyl)-N-tosylaniline (3b) in the presence of 10 mol% of PdBr2 in toluene at 80 degrees C gave 3-methoxymethyl-2-propyl-1-tosylindole (4a) and 3-methoxymethyl-2-phenyl-1-tosylindole (4b) in 33 and 33% yields, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.039

文献信息

• Synthesis of 2,3-Disubstituted Benzofurans by Platinum−Olefin-Catalyzed Carboalkoxylation of <i>o</i>-Alkynylphenyl Acetals
  作者：Itaru Nakamura、Yuya Mizushima、Yoshinori Yamamoto

  DOI：10.1021/ja055202f

  日期：2005.11.1

  The PtCl2-catalyzed cyclization reaction of o-alkynylphenyl acetals 1 in the presence of 1,5-cyclooctadiene produces 3-(alpha-alkoxyalkyl)benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl)phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl)phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal (1f) in the presence of 2 mol % of platinum(II) chloride and 8 mol % of 1,5-cyclooctadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively.
• Synthesis of 2,3-disubstituted benzofurans and indoles by π-Lewis acidic transition metal-catalyzed cyclization of ortho-alkynylphenyl O,O- and N,O-acetals
  作者：Itaru Nakamura、Yuya Mizushima、Uichiro Yamagishi、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2007.03.039

  日期：2007.8

  The PtCl2-catalyzed cyclization reaction of ortho-alkynylphenyl acetals 1 in the presence of COD (1,5-cyclooctadiene) produces 3-(alpha-alkoxyalkyl) benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl) phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl) phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl) phenyl acetal (1f) in the presence of 2 mol% of platinum(II) chloride and 8 mol% of 1,5-cycloocatadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively. Moreover, the reaction of N-methoxymethyl-2-alkynylanilines 3 was catalyzed by PdBr2, affording the corresponding 2,3-disubstituted indoles 4 in moderate yields. For example, the reaction of N-methoxymethyl-2-(1-pentynyl)- N-tosylaniline (3a) and N-methoxymethyl-2-(phenylethynyl)-N-tosylaniline (3b) in the presence of 10 mol% of PdBr2 in toluene at 80 degrees C gave 3-methoxymethyl-2-propyl-1-tosylindole (4a) and 3-methoxymethyl-2-phenyl-1-tosylindole (4b) in 33 and 33% yields, respectively. (c) 2007 Elsevier Ltd. All rights reserved.