3-phenyl-2-n-propyl-2,3-dihydro-isoindol-1-one

• 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-phenyl-2-n-propyl-2,3-dihydro-isoindol-1-one
• 英文别名: 3-phenyl-2-propylisoindolin-1-one；3-phenyl-2-propyl-3H-isoindol-1-one
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: MJYBXUNRNZKJPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-n-propyl-2,3-dihydro-isoindol-1-one 在 2,2'-bipyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到3-hydroxy-3-phenyl-2-propyl-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  A direct arylation-oxidation route to 3-arylisoindolinone inhibitors of MDM2-p53 interaction

  摘要：

  A route to the MDM2-p53 inhibitor isoindolinone pharmacophore from a pre-formed phthalimide is detailed. The route involves treatment of 3-hydroxy-2-(n-propyl)isoindolinone with a substituted benzene in the presence of triflic acid. The resulting 3-aryl-2-(n-propyl)isoindolinones are then oxidized to the corresponding 3-hydroxy-3-aryl-2-(n-propyl) isoindolinones by treatment with 2,2'-bipyridinium chlorochromate. The benzylic oxidation represents a rather rare oxochromium (VI)-mediated reaction in which a selective C-H to C-OH transformation occurs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.076
• 作为产物：
  描述：

  N-丙基酞酰亚胺 在 aluminum amalgam 、 三氟甲磺酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-phenyl-2-n-propyl-2,3-dihydro-isoindol-1-one
  参考文献：
  名称：

  A direct arylation-oxidation route to 3-arylisoindolinone inhibitors of MDM2-p53 interaction

  摘要：

  A route to the MDM2-p53 inhibitor isoindolinone pharmacophore from a pre-formed phthalimide is detailed. The route involves treatment of 3-hydroxy-2-(n-propyl)isoindolinone with a substituted benzene in the presence of triflic acid. The resulting 3-aryl-2-(n-propyl)isoindolinones are then oxidized to the corresponding 3-hydroxy-3-aryl-2-(n-propyl) isoindolinones by treatment with 2,2'-bipyridinium chlorochromate. The benzylic oxidation represents a rather rare oxochromium (VI)-mediated reaction in which a selective C-H to C-OH transformation occurs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.076

文献信息

• Addition of Transiently-Generated Methyl <i>o</i>-Lithiobenzoate to Imines. An Isoindolone Annulation
  作者：James B. Campbell、Robert F. Dedinas、Sally A. Trumbower-Walsh

  DOI：10.1021/jo960582w

  日期：1996.1.1

  Addition of phenyllithium to a mixture of an imine, methyl o-iodobenzoate, and BF3 . etherate at -105 degrees C gives good to excellent yields of isoindolones. The transient formation of methyl o-lithiobenzoate is proposed, which is formed by a rapid lithium/iodide exchange reaction of the phenyllithium with methyl o-iodobenzoate in the presence of the imine. The transiently generated anions can then be captured by the BF3-activated imines to form the isoindolones in good to high yield. The reactions conditions are sufficiently mild, and selective, to permit functional groups such carbmethoxy and aryl bromide, which could otherwise react with the added PhLi, to be tolerated.
• Hamed, Atef A.; Zeid, Ibrahim F.; Manaa, Alaa A., Zeitschrift fur Naturforschung, B: Chemical Sciences, 2009, vol. 64, # 5, p. 555 - 564
  作者：Hamed, Atef A.、Zeid, Ibrahim F.、Manaa, Alaa A.

  DOI：——

  日期：——
• Okuro Kazumi, Inokawa Naoki, Miura Masahiro, Nomura Masakatsu, J. Chem. Res. Synop, (1994) N 10, S 372-373
  作者：Okuro Kazumi, Inokawa Naoki, Miura Masahiro, Nomura Masakatsu

  DOI：——

  日期：——
• ISOINDOLIN-1-ONE DERIVATIVES
  申请人：Cancer Research Technology Limited

  公开号：EP1786773B1

  公开（公告）日：2017-03-01
• A direct arylation-oxidation route to 3-arylisoindolinone inhibitors of MDM2-p53 interaction
  作者：Richard K. Dempster、Frederick A. Luzzio

  DOI：10.1016/j.tetlet.2011.07.076

  日期：2011.9

  A route to the MDM2-p53 inhibitor isoindolinone pharmacophore from a pre-formed phthalimide is detailed. The route involves treatment of 3-hydroxy-2-(n-propyl)isoindolinone with a substituted benzene in the presence of triflic acid. The resulting 3-aryl-2-(n-propyl)isoindolinones are then oxidized to the corresponding 3-hydroxy-3-aryl-2-(n-propyl) isoindolinones by treatment with 2,2'-bipyridinium chlorochromate. The benzylic oxidation represents a rather rare oxochromium (VI)-mediated reaction in which a selective C-H to C-OH transformation occurs. (C) 2011 Elsevier Ltd. All rights reserved.