4-(3,4-dihydro-6-methoxy-1H-isochromen-1-yl)benzonitrile | 1220970-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(3,4-dihydro-6-methoxy-1H-isochromen-1-yl)benzonitrile
• 英文别名: 4-(6-methoxy-3,4-dihydro-1H-isochromen-1-yl)benzonitrile
• CAS: 1220970-38-6
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: FBFGKHYBXIWZEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-甲氧基苯基)乙醇 、 4-氰基苯甲醛 在 bismuth(lll) trifluoromethanesulfonate 、 水 作用下， 以 甲苯 为溶剂， 以95%的产率得到4-(3,4-dihydro-6-methoxy-1H-isochromen-1-yl)benzonitrile
  参考文献：
  名称：

  Bismuth Triflate as a Safe and Readily Handled Source of Triflic Acid: Application to the Oxa–Pictet–Spengler Reaction

  摘要：

  The oxa-Pictet-Spengler reaction with various aldehydes and -arylethanol yields 1-substituted-isochromans in the presence of bismuth triflate as catalyst in good yields. The method was extended to O,O-acetals to afford the corresponding 1,1-disubstituted-isochromans in good yields. These studies also provide insights into the catalytic role of triflic acid generated upon hydrolysis of Bi(OTf)3 by residual water. The low toxicity and easy handling of Bi(OTf)3 by comparison with triflic acid make these procedures an attractive method to provide isochromans in good to excellent yields.

  DOI：

  10.1080/00397910903026715

文献信息

• Bismuth Triflate as a Safe and Readily Handled Source of Triflic Acid: Application to the Oxa–Pictet–Spengler Reaction
  作者：Benaissa Bouguerne、Pascal Hoffmann、Christian Lherbet

  DOI：10.1080/00397910903026715

  日期：2010.2.26

  The oxa-Pictet-Spengler reaction with various aldehydes and -arylethanol yields 1-substituted-isochromans in the presence of bismuth triflate as catalyst in good yields. The method was extended to O,O-acetals to afford the corresponding 1,1-disubstituted-isochromans in good yields. These studies also provide insights into the catalytic role of triflic acid generated upon hydrolysis of Bi(OTf)3 by residual water. The low toxicity and easy handling of Bi(OTf)3 by comparison with triflic acid make these procedures an attractive method to provide isochromans in good to excellent yields.