4-phenoxyphthalimide | 301208-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-phenoxyphthalimide
• 英文别名: 5-Phenoxyphthalimide；5-phenoxyisoindole-1,3-dione
• CAS: 301208-03-7
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: ADMMGQSIWCCWJV-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: water (7732-18-5))
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenoxyphthalimide 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 17.0h， 生成 5-苯氧基异苯并呋喃-1-(3H)-酮
  参考文献：
  名称：

  一种取代苯酞类化合物的制备方法及其中间 体

  摘要：

  本发明公开了一种取代苯酞类化合物的制备方法及其中间体。本发明的取代苯酞类化合物的制备方法包括下述步骤：在水中，在酸性条件下，将化合物B进行环合反应，得到化合物A即可。该方法工艺简单、成本较低、三废较少，适于工业化生产。

  公开号：

  CN107188875B
• 作为产物：
  描述：

  4-苯氧基邻苯二甲腈 在 硝酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 4-phenoxyphthalimide
  参考文献：
  名称：

  单-和双-苯氧基取代的3-(喹啉-2-基亚甲基)异吲哚啉-1-酮及其硼络合物。薄膜的合成、光物理性质和电导率

  摘要：

  在氧化锌存在下，将4-苯氧基邻苯二甲酰亚胺或4,5-二苯氧基邻苯二甲酰亚胺与喹哪啶一起加热，形成(E ,Z )-5(6)-苯氧基-3-(喹啉-2-亚甲基)异吲哚啉-1-酮和(E, Z )-5,6-二苯氧基-3-(喹啉-2-亚甲基)异吲哚啉-1-酮。在Et 3 N存在下，在甲苯中与BF 3 ‧Et 2 O反应，合成了BODIPY的不对称类似物，即( Z )-2-(二氟硼基)-5(6)-苯氧基-3-(喹啉-2-基亚甲基)异吲哚啉-1-酮和( Z )-2-二氟硼基-5,6-二苯氧基-3-(喹啉-2-基亚甲基)异吲哚啉。分别为 olin-1-one。通过元素分析数据确认了合成化合物的结构、质谱、振动和核磁共振光谱。该配体具有低荧光量子产率（相对于标准品高达 0.14）和显着的斯托克斯位移（高达 140 nm）。相比之下，配合物表现出高量子产率（高达 0.44）和小斯托克斯位移（7-8 nm）。配合物的荧光寿命接近3

  DOI：

  10.1016/j.dyepig.2023.111523

文献信息

• Transition metal-free 1,3-dimethylimidazolium hydrogen carbonate catalyzed hydration of organonitriles to amides
  作者：Praveen Kumar Verma、Upendra Sharma、Manju Bala、Neeraj Kumar、Bikram Singh

  DOI：10.1039/c2ra22868h

  日期：——

  An efficient hydration of organonitriles to the corresponding amides was accomplished using 1,3-dimethylimidazolium hydrogen carbonate as an organocatalyst. The developed catalytic method was also applicable for the synthesis of metal phthalocyanines.

  使用1,3-二甲基咪唑啉鎓碳酸氢盐作为有机催化剂，实现了有机腈高效水合转化为相应的酰胺。所开发的催化方法同样适用于金属酞菁的合成。
• [EN] A PROCESS FOR PREPARING 5-PHENOXY-1(3H)ISOBENZOFURANONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-PHÉNOXY-1(3H) ISOBENZOFURANONE
  申请人：KINGCHEM LIFE SCIENCE LLC

  公开号：WO2018140186A1

  公开（公告）日：2018-08-02

  The disclosure provides a simple and efficient method for producing a compound of Formula I. The method includes treating an N-substitututed-4-nitro-phthalimide of Formula VII with sodium or potassium phenoxide to form an N-substituted-4-phenoxy-phthalimide of Formula VIII and then treating the N-substituted-4-phenoxy-phthalimide of Formula VIII with zinc in the presence of a base to give 5-phenoxy- l(3H)-isobenzofuranone of Formula I, its isomer of 6-phenoxy- l (3H)-isobenzofuranone of Formula la, and alkyl amine or aryl amine NH2R (Formula IX)

  该公开提供了一种简单高效的方法，用于制备化合物I的方法。该方法包括将式VII的N-取代-4-硝基邻苯二甲酰亚胺与钠或钾苯酚处理，形成式VIII的N-取代-4-苯氧基邻苯二甲酰亚胺，然后在碱存在下将式VIII的N-取代-4-苯氧基邻苯二甲酰亚胺与锌处理，得到式I的5-苯氧基-1(3H)-异苯并呋喃酮，其异构体6-苯氧基-1(3H)-异苯并呋喃酮和烷基胺或芳基胺NH2R（式IX）。
• Process for preparing 5-phenoxy-1(3)isobenzofuranone
  申请人：KINGCHEM LIFE SCIENCE LLC

  公开号：US10611745B2

  公开（公告）日：2020-04-07

  The disclosure provides a simple and efficient method for producing a compound of Formula I. The method includes treating an N-substituted-4-nitro-phthalimide of Formula VII with sodium or potassium phenoxide to form an N-substituted-4-phenoxy-phthalimide of Formula VIII and then treating the N-substituted-4-phenoxy-phthalimide of Formula VIII with, for example zinc, in the presence of a base to give 5-phenoxy-1(3H)-isobenzofuranone of Formula I, its isomer of 6-phenoxy-1 (3H)-isobenzofuranone of Formula Ia, and alkyl amine or aryl amine NH2R (Formula IX)

  本公开提供了一种生产式 I 化合物的简单而有效的方法。该方法包括用氧化钠或氧化钾处理式 VII 的 N-取代-4-硝基邻苯二甲酰亚胺，形成式 VIII 的 N-取代-4-苯氧基邻苯二甲酰亚胺，然后用例如锌，在碱存在下，得到式 I 的 5-苯氧基-1(3H)-异苯并呋喃酮、其异构体式 Ia 的 6-苯氧基-1(3H)-异苯并呋喃酮和烷基胺或芳基胺 NH2R（式 IX）
• Inhibition of monoamine oxidase by C5-substituted phthalimide analogues
  作者：Clarina I. Manley-King、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2011.06.070

  日期：2011.8

  Literature reports that isatin as well as C5- and C6-substituted isatin analogues are reversible inhibitors of human monoamine oxidase (MAO) A and B. In general, C5- and C6-substitution of isatin leads to enhanced binding affinity to both MAO isozymes compared to isatin and in most instances result in selective binding to the MAO-B isoform. Crystallographic and modeling studies suggest that the isatin ring binds to the substrate cavities of MAO-A and -B and is stabilized by hydrogen bond interactions between the NH and the C2 carbonyl oxygen of the dioxoindolyl moiety and water molecules present in the substrate cavities of MAO-A and -B. Based on these observations and the close structural resemblances between isatin and its phthalimide isomer, a series of phthalimide analogues were synthesized and evaluated as MAO inhibitors. While phthalimide and N-aryl-substituted phthalimides were found to be weak MAO inhibitors, phthalimide homologues containing C5 substituents were potent reversible inhibitors of recombinant human MAO-B with IC(50) values ranging from 0.007 to 2.5 mu M and moderately potent reversible inhibitors of recombinant human MAO-A with IC(50) values ranging from 0.22 to 9.0 mu M. By employing molecular docking the importance of hydrogen bonding between the active sites of MAO-A and -B and the phthalimide inhibitors are highlighted. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and spectral properties of unsymmetrical benzoporphyrins containing phenoxy groups or quinoxaline fragments
  作者：N. E. Galanin、G. P. Shaposhnikov

  DOI：10.1134/s1070428007070226

  日期：2007.7

  Condensation of phthalimide and 4-tert-butylphthalimide with zinc(II) acetate gave 3-(3-oxo-2,3-dihydro-1H-isoindol-1-ylidenemethyl)-1H-isoindol-1-one and 5-tert-butyl-3-(5-tert-butyl-3-oxo-2,3-dihydro-1H-isoindol-1-ylidenemethyl)-1H-isoindol-1-one, respectively. Their reactions with 4-phenoxyphthalimide and quinoxaline-2,3-dicarboximide in the presence of Zn(OAc)(2) led to the formation of zinc complexes of cis-4,4'-diphenoxytetrabenzoporphyrin and cis-di(4-tert-butylbenzo)diquinoxalinoporphyrin. The complexes were converted into the free bases by treatment with sulfuric acid. Spectral properties of the obtained porphyrin derivatives were studied.