3-hydroxy-3-(p-tolyl)isoindolin-1-one | 39127-18-9

• 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: 3-hydroxy-3-(p-tolyl)isoindolin-1-one
• 英文别名: 3-Hydroxy-3-(4-methylphenyl)-2,3-dihydro-1h-isoindol-1-one；3-hydroxy-3-(4-methylphenyl)-2H-isoindol-1-one
• CAS: 39127-18-9
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: CWNQPIKGKPUCEG-UHFFFAOYSA-N

物化性质

• 沸点：
  518.8±50.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(p-tolyl)isoindolin-1-one 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到3-(4-Methylphenyl)-1-oxo-2,3-dihydroisoindol
  参考文献：
  名称：

  一类具有BRD4抑制活性的化合物、其制备方法及用途

  摘要：

  本发明公开了一种具有BRD4抑制活性的化合物、其制备方法及用途。本发明的具有BRD4抑制活性的化合物，结构如式I所示，各取代基的定义如说明书和权利要求书所述。本发明的化合物，具有很高的溴结构域蛋白抑制活性，特别是靶向BRD4的抑制活性，可用于治疗或/和预防由溴结构域蛋白介导的相关疾病。

  公开号：

  CN112625036A
• 作为产物：
  描述：

  2-(4-methylbenzoyl)benzonitrile 在 三氟乙酸 、 水 作用下， 反应 5.0h， 以76%的产率得到3-hydroxy-3-(p-tolyl)isoindolin-1-one
  参考文献：
  名称：

  o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group

  摘要：

  2-Cyanobenzophenones were synthesized by reaction of 2-bromobenzophenones with copper(I) cyanide in DMF, and their transformations involving acid hydrolysis of the cyano group were studied. Reactions of o-benzoylbenzonitriles with trifluoroacetic acid in the presence or in the absence of sulfuric acid afforded 3-hydroxyphthalimidines in high yields. Under analogous conditions, benzonitriles having no acyl group in the ortho position were converted to the corresponding benzamides. 2-Cyanobenzophenones reacted with sulfuric acid in the absence of trifluoroacetic acid to give only substituted anthraquinones.

  DOI：

  10.1134/s1070428018030065

文献信息

• Organocatalytic Synthesis of α-Triphenylmethylamines from Diarylketimines and Phenols
  作者：Danijel Glavač、Nikola Topolovčan、Matija Gredičak

  DOI：10.1021/acs.joc.0c02225

  日期：2020.11.6

  formal Betti reaction between variously substituted phenols and benzophenone-derived imines to afford α-triphenylmethylamines is reported. The key to the success of this transformation is the in situ generation of the reactive benzophenone iminium species under organocatalytic conditions. Different phenols reacted smoothly, enabling the synthesis of an array of α-triphenylmethylamines, which are highly

  据报道，在各种取代的苯酚和二苯甲酮衍生的亚胺之间进行正式的Betti反应，得到α-三苯甲胺。该转化成功的关键是在有机催化条件下原位生成反应性二苯甲酮亚胺。不同的苯酚反应平稳，可以合成一系列α-三苯甲胺，这是生物活性分子和化学传感器中极有价值的结构图案。
• Enantioselective [3 + 2] annulation via C–H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes
  作者：Takahiro Nishimura、Midori Nagamoto、Yusuke Ebe、Tamio Hayashi

  DOI：10.1039/c3sc52379a

  日期：——

  Enantioselective [3 + 2] annulation between 1,3-dienes and N-acyl ketimines in situ generated from 3-aryl-3-hydroxyisoindolin-1-ones proceeded via C–H activation to give spiroaminoindane derivatives in high yields with high regio- and enantioselectivity, which is realized by use of an Ir/chiral diene catalyst.

  手性二烯基铱催化剂实现了1,3-二烯与3-芳基-3-羟基异吲哚-1-酮原位生成的N-酰基乙烯亚胺之间的[3 + 2]环化反应，通过C-H活化途径，高产率、高区域选择性和高对映选择性地合成了螺氨基茚衍生物。
• Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals
  作者：Josipa Suć、Irena Dokli、Matija Gredičak

  DOI：10.1039/c5cc08813e

  日期：——

  Chiral Brønsted acid catalyzed synthesis of N(acyl),S-acetals from in situ generated ketimines proceeds in high yields and enantioselectivities.

  手性Brønsted酸催化的合成，从现场生成的酮亚胺中生成N(酰),S-缩醛，产率高，对映选择性好。
• Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N , S -ketals
  作者：Rajshekhar A. Unhale、Nagaraju Molleti、Nirmal K. Rana、Sivasankaran Dhanasekaran、Subhrajyoti Bhandary、Vinod K. Singh

  DOI：10.1016/j.tetlet.2016.11.114

  日期：2017.1

  The chiral Brønsted acid catalyzed enantioselective 1,2-addition of thiols to in situ generated ketimines, derived from 3-hydroxyisoindolinones, has been studied. The protocol provides a variety of isoindolinone-derived N,S-ketals in up to 98% yield and up to 99% enantioselectivity. The products have been converted to a known non-nucleoside HIV-1 reverse transcriptase inhibitor and a 1,3-thiazine derivative

  研究了手性布朗斯台德酸催化硫醇对映体选择性1,2-加成到原位生成的3-亚甲基异吲哚啉酮酮中。该方案以高达98％的收率和高达99％的对映选择性提供了各种异吲哚啉酮衍生的N，S-缩酮。产物已转化为已知的非核苷HIV-1逆转录酶抑制剂和1,3-噻嗪衍生物。
• A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with <i>in situ</i> generated <i>N</i>-acyl ketimines
  作者：Rajshekhar A. Unhale、Milon M. Sadhu、Sumit K. Ray、Rayhan G. Biswas、Vinod K. Singh

  DOI：10.1039/c8cc01436a

  日期：——

  A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore

  在该文献中已经证明了手性磷酸催化α-重氮酯与原位生成的由3-羟基异吲哚满酮衍生的N-酰基酮亚胺的不对称曼尼希型反应。以高收率（高达99％）和优异的对映选择性（高达99％ee）提供了多种带有季立构中心的基于异吲哚啉酮的α-氨基重氮酯。此外，通过加合物的重氮部分的氢化描述了产物的合成效用。