1,3-dihydroisobenzofuranyl 2-formylbenzyl ether | 65539-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,3-dihydroisobenzofuranyl 2-formylbenzyl ether
• 英文别名: 2-(1,3-dihydro-isobenzofuran-1-yloxymethyl)-benzaldehyde；2-(1,3-Dihydro-2-benzofuran-1-yloxymethyl)benzaldehyde
• CAS: 65539-67-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: IJRIPXWIPRPHDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二氢异苯并呋喃-1-醇 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-dihydroisobenzofuranyl 2-formylbenzyl ether 、 丙酸,2,2-二甲基-,(2-formylphenyl)甲基酯
  参考文献：
  名称：

  Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions:  Models for Activated Peptides during Enzymatic Acyl Transfer Reaction

  摘要：

  The highly twisted amide 2 served as a selective acylating agent; for dials under neutral conditions. The reaction of primary-secondary dials with 2 led to the corresponding primary alkyl monopivalates. For dials containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5-10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.

  DOI：

  10.1021/jo9522015

文献信息

• Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions:  Models for Activated Peptides during Enzymatic Acyl Transfer Reaction
  作者：Shinji Yamada、Takayuki Sugaki、Kazuhiro Matsuzaki

  DOI：10.1021/jo9522015

  日期：1996.1.1

  The highly twisted amide 2 served as a selective acylating agent; for dials under neutral conditions. The reaction of primary-secondary dials with 2 led to the corresponding primary alkyl monopivalates. For dials containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5-10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.