4-Formyl-phthalid | 90484-24-5

• 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: 4-Formyl-phthalid
• 英文别名: 1-oxo-1,3-dihydro-isobenzofuran-4-carbaldehyde；1-Oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde；1-oxo-3H-2-benzofuran-4-carbaldehyde
• CAS: 90484-24-5
• 化学式: C₉H₆O₃
• 分子量: 162.145
• InChiKey: AHVCKXVOVUUHOE-UHFFFAOYSA-N

物化性质

• 沸点：
  410.6±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二甲基苯甲酸甲酯 在 palladium on activated charcoal calcium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 水 、 氢气 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 180.0 ℃ 、275.79 kPa 条件下， 反应 57.0h， 生成 4-Formyl-phthalid
  参考文献：
  名称：

  Aromatische Spirane, 21. Mitt: Darstellung von Methylphthalaldehyds�uren und ihren Ethylund Methylestern als Synthone f�r Synthesen von methylierten 2,2?-Spirobiindandionen

  摘要：

  The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.

  DOI：

  10.1007/bf00807401

文献信息

• JPS5527109A
  申请人：——

  公开号：JPS5527109A

  公开（公告）日：1980-02-27
• US4182876A
  申请人：——

  公开号：US4182876A

  公开（公告）日：1980-01-08
• [EN] ESTER COMPOUND<br/>[FR] COMPOSÉ ESTER<br/>[JA] エステル化合物
  申请人：DAIICHI SANKYO CO LTD

  公开号：WO2020153431A1

  公开（公告）日：2020-07-30

  本発明の課題は、SIRT6の活性化作用を有する特定アンテドラッグとしての化学構造を有する、炎症性の疾患の予防及び治療のための有効成分として有用な化合物を提供することである。本発明は、式(1)の化合物、又は、その薬学上許容される塩に関する。（式(1)中の記号はそれぞれ、明細書に記載された定義と同様である。）
• Aromatische Spirane, 21. Mitt: Darstellung von Methylphthalaldehyds�uren und ihren Ethylund Methylestern als Synthone f�r Synthesen von methylierten 2,2?-Spirobiindandionen
  作者：H. K. Neudeck

  DOI：10.1007/bf00807401

  日期：1996.2

  The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.