ethyl 5-(benzoylamino)-2-(ethoxycarbonyl)-methyl-4-[(Z )-2-methoxyethenyl]benzoate

• 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: ethyl 5-(benzoylamino)-2-(ethoxycarbonyl)-methyl-4-[(Z )-2-methoxyethenyl]benzoate
• 英文别名: ethyl 5-benzamido-2-(2-ethoxy-2-oxoethyl)-4-[(Z)-2-methoxyethenyl]benzoate
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: AEZUKWCNPKIJCX-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-(benzoylamino)-2-(ethoxycarbonyl)-methyl-4-[(Z )-2-methoxyethenyl]benzoate 在 盐酸 作用下， 以 乙醇 为溶剂， 以78%的产率得到ethyl 1-benzoyl-5-(ethoxycarbonyl)-methyl-1H-indole-6-carboxylate
  参考文献：
  名称：

  An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones

  摘要：

  The cycloaddition of (Z)-1-methoxybut-1-en-3-yne (2) with 5,6-disubstituted 3-acylamino-2H-pyran-2-ones 1 under microwave-irradiation conditions, with classical heating or at high-pressures (13-15 kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxy-ethenyl moiety. In some cases, at high-pressures after long reaction times, 2,2-dimethoxyethyl products 4 were obtained. Adducts 3 and 4 can be cyclized under mild conditions into 1,5,6-trisubstituted indole derivatives 5. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.099
• 作为产物：
  描述：

  ethyl 3-(benzoylamino)-6-(ethoxycarbonyl)methyl-2-oxo-2H-pyran-5-carboxylate 、 (Z)-1-methoxybut-1-en-3-yne 以 甲醇 、 甲苯 为溶剂， 150.0 ℃ 、800.01 kPa 条件下， 反应 1.92h， 以82%的产率得到ethyl 5-(benzoylamino)-2-(ethoxycarbonyl)-methyl-4-[(Z )-2-methoxyethenyl]benzoate
  参考文献：
  名称：

  An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones

  摘要：

  The cycloaddition of (Z)-1-methoxybut-1-en-3-yne (2) with 5,6-disubstituted 3-acylamino-2H-pyran-2-ones 1 under microwave-irradiation conditions, with classical heating or at high-pressures (13-15 kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxy-ethenyl moiety. In some cases, at high-pressures after long reaction times, 2,2-dimethoxyethyl products 4 were obtained. Adducts 3 and 4 can be cyclized under mild conditions into 1,5,6-trisubstituted indole derivatives 5. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.099

文献信息

• An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1016/j.tet.2007.10.099

  日期：2008.1

  The cycloaddition of (Z)-1-methoxybut-1-en-3-yne (2) with 5,6-disubstituted 3-acylamino-2H-pyran-2-ones 1 under microwave-irradiation conditions, with classical heating or at high-pressures (13-15 kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxy-ethenyl moiety. In some cases, at high-pressures after long reaction times, 2,2-dimethoxyethyl products 4 were obtained. Adducts 3 and 4 can be cyclized under mild conditions into 1,5,6-trisubstituted indole derivatives 5. (c) 2007 Elsevier Ltd. All rights reserved.