3-hydroxy-3-(4-methoxyphenyl)isoindolin-1-one | 92553-10-1

• 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-(4-methoxyphenyl)isoindolin-1-one
• 英文别名: 3-hydroxy-3-(4-methoxyphenyl)-2H-isoindol-1-one
• CAS: 92553-10-1
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: LUFCKFOOXDPWBV-UHFFFAOYSA-N

物化性质

• 沸点：
  537.3±50.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(4-methoxyphenyl)isoindolin-1-one 在 lithium hydroxide monohydrate 、 (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 18.25h， 生成 phenyl hydrogen ((+)-1-(4-methoxyphenyl)-3-oxoisoindolin-1-yl)phosphonate
  参考文献：
  名称：

  的对映体选择性Hydrophosphonylation原位生成Ñ酰基酮亚胺催化由BINOL衍生磷酸

  摘要：

  通过BINOL衍生的磷酸催化原位生成的酮亚胺的不对称氢膦酰化反应，描述了一种药理学上有趣的基于异吲哚啉酮的α-氨基膦酸酯的有效途径。该反应在环境温度下顺利进行，以高收率和优异的对映体比率（高达98.5：1.5 er）提供了多种具有嵌入立体异构中心的季立体形成中心的α-氨基膦酸酯。还描述了产物向有价值的合成中间体的几种有趣的转化。

  DOI：

  10.1021/acs.orglett.6b03623
• 作为产物：
  描述：

  2-(4-甲氧基苯甲酰基)苯甲腈 在 三氟乙酸 、 水 作用下， 反应 1.0h， 以92%的产率得到3-hydroxy-3-(4-methoxyphenyl)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

• Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C–H activation: unexpected inversion of the enantioselectivity induced by protic acids
  作者：Midori Nagamoto、Daisuke Yamauchi、Takahiro Nishimura

  DOI：10.1039/c6cc01398h

  日期：——

  A cationic iridium/binap catalyst enabled the asymmetric [3 + 2] annulation of cyclic N-acyl ketimines with internal alkynes via C-H activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical...

  阳离子铱/ BINAP催化剂可通过CH活化使环状N-酰基酮亚胺与内部炔烃不对称[3 + 2]环化，从而获得具有高对映选择性的螺氨基茚衍生物。立体化学...
• 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。
• Synthesis of Functionalized Isoindolinones via Calcium Catalyzed Generation and Trapping of <i>N</i>-Acyliminium Ions
  作者：Ashley J. Basson、Mark G. McLaughlin

  DOI：10.1021/acs.joc.0c00482

  日期：2020.4.17

  Herein we report our full investigation into the calcium catalyzed generation and trapping of N-acyliminium ions from readily available 3-hydroxyisoindolinones. We have successfully employed a range of traditional nucleophiles including carbon, nitrogen, and sulfur containing reactive partners. The reaction is tolerant to a wide range of functionalities and provides high value scaffolds in good to

  本文中，我们报告了对钙催化的生成和从易得的3-羟基异吲哚满酮中捕获N-酰基亚胺离子的全面研究。我们已经成功地使用了一系列传统的亲核试剂，包括含碳，氮和硫的反应性伙伴。该反应可耐受多种功能，并以高至优异的产率提供高价值的支架。