N-(4-hydroxyphenyl)-1-oxo-isoindoline | 4778-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(4-hydroxyphenyl)-1-oxo-isoindoline
• 英文别名: 1H-Isoindol-1-one, 2,3-dihydro-2-(4-hydroxyphenyl)-；2-(4-hydroxyphenyl)-3H-isoindol-1-one
• CAS: 4778-80-7
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: NDERTONLGOTDER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxyphenyl)-1-oxo-isoindoline 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-{4-[2-hydroxy-3-(4-methylpiperazino)propoxy]phenyl}-1-oxo-isoindoline
  参考文献：
  名称：

  Synthesis of 4-(1-oxo-isoindoline) and 4-(5,6-dimethoxy-1-oxo-isoindoline)-substituted phenoxypropanolamines and their β1-, β2-adrenergic receptor binding studies

  摘要：

  Phenoxypropanolamines with 1-oxo-isoindoline (12-16) and 5,6-dimethoxy-1-oxo-isoindoline groups (17-20) at the para position were synthesized. beta(1), beta(2)-Adrenergic receptor binding affinities for the synthesized compounds were tested and compared with propranolol and atenolol. It was found that the incorporation of para-amidic functionality within the 1-oxo-isoindoline ring and 5,6-dimethoxy-1-oxo-isoindoline ring system led to a high degree of cardio selectivity in the phenoxypropanolamines. Two of the compounds 12 and 20 possessed beta(1)-adrenergic receptor affinity comparable with that of atenolol and both showed a better cardioselectivity than atenotol. Both 12 and 20 are undergoing further pharmacological evaluation. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.05.001
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 N-(4-hydroxyphenyl)-1-oxo-isoindoline
  参考文献：
  名称：

  Rowe et al., Journal of the Chemical Society, 1926, p. 703

  摘要：

  DOI：

文献信息

• Highly Efficient Synthesis of <i>N</i>-Substituted Isoindolinones and Phthalazinones Using Pt Nanowires as Catalysts
  作者：Linyan Shi、Lei Hu、Jiaqing Wang、Xueqin Cao、Hongwei Gu

  DOI：10.1021/ol300471a

  日期：2012.4.6

  coupling and intramolecular amidation of 2-carboxybenzaldehyde and amines. This one-pot synthesis gives excellent yields using ultrathin Pt nanowires as catalysts under 1 bar of hydrogen. These unsupported catalysts can also be used for the synthesis of phthalazinones in high yield when hydrazine or phenyl hydrazine is used instead of amines.

  通过还原性C–N偶联以及2-羧基苯甲醛和胺的分子内酰胺化，已成功合成了一系列N取代的异吲哚啉酮。使用超薄Pt纳米线作为催化剂，在1 bar的氢气压力下，这种一锅法合成方法的收率很高。当使用肼或苯基肼代替胺时，这些未负载的催化剂也可用于高产率地合成邻苯二氮酮。
• Murahashi et al., Nippon Kagaku Zasshi, 1958, vol. 79, p. 68,79
  作者：Murahashi et al.

  DOI：——

  日期：——
• Jindal, Dharam Paul; Singh, Babita; Sharma, Neelam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 11, p. 2808 - 2813
  作者：Jindal, Dharam Paul、Singh, Babita、Sharma, Neelam、Coumar, Mohane S.、Bruni, Giancarlo、Massarelli, Paola

  DOI：——

  日期：——
• KAMEHYAMA, TSUTOMU;INOUEH, NOBORU
  作者：KAMEHYAMA, TSUTOMU、INOUEH, NOBORU

  DOI：——

  日期：——
• NODA, KANDZI;NAKAGAVA, NOBORU;MOTOMURA, TOSIXARU
  作者：NODA, KANDZI、NAKAGAVA, NOBORU、MOTOMURA, TOSIXARU

  DOI：——

  日期：——