2-Benzyloxymethoxy-1-(1-ethoxy-ethoxy)-5-[(E)-3-(1-ethoxy-ethoxy)-propenyl]-3-iodo-benzene | 870011-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Benzyloxymethoxy-1-(1-ethoxy-ethoxy)-5-[(E)-3-(1-ethoxy-ethoxy)-propenyl]-3-iodo-benzene
• CAS: 870011-38-4
• 化学式: C₂₅H₃₃IO₆
• 分子量: 556.438
• InChiKey: IPKJXZIVNUJIEA-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  32.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-Benzyloxymethoxy-1-(1-ethoxy-ethoxy)-5-[(E)-3-(1-ethoxy-ethoxy)-propenyl]-3-iodo-benzene 在 三乙胺 copper(l) iodide 、 1,5-cis,cis-cyclooctadiene 、 三苯基膦 、 platinum(II) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 3-Benzyloxymethyl-7-(1-ethoxy-ethoxy)-2-[4-(1-ethoxy-ethoxy)-3-methoxy-phenyl]-5-[(E)-3-(1-ethoxy-ethoxy)-propenyl]-benzofuran
  参考文献：
  名称：

  Synthesis of 2,3-Disubstituted Benzofurans by Platinum−Olefin-Catalyzed Carboalkoxylation of o-Alkynylphenyl Acetals

  摘要：

  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.

  DOI：

  10.1021/ja055202f
• 作为产物：
  描述：

  苄基氯甲基醚 、 2-(1-Ethoxy-ethoxy)-4-[(E)-3-(1-ethoxy-ethoxy)-propenyl]-6-iodo-phenol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以100%的产率得到2-Benzyloxymethoxy-1-(1-ethoxy-ethoxy)-5-[(E)-3-(1-ethoxy-ethoxy)-propenyl]-3-iodo-benzene
  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