3-hydroxy-2-(1-methyl-1-phenylethyl)-2,3-dihydro-1H-isoindol-1-one | 249764-70-3

• 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-2-(1-methyl-1-phenylethyl)-2,3-dihydro-1H-isoindol-1-one
• 英文别名: 3-Hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone；3-hydroxy-2-(2-phenylpropan-2-yl)-3H-isoindol-1-one
• CAS: 249764-70-3
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: KJAMARCGRNWFNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  3-hydroxy-2-(1-methyl-1-phenylethyl)-2,3-dihydro-1H-isoindol-1-one 在 重铬酸吡啶 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-Methylsulfanyl-2-(2-phenylpropan-2-yl)isoindole-1,3-dione
  参考文献：
  名称：

  N-Cumyl Benzamide, Sulfonamide, and Aryl O-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics

  摘要：

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.

  DOI：

  10.1021/ol990846b
• 作为产物：
  描述：

  2-苯基-2-丙醇 在 lithium aluminium tetrahydride 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 生成 3-hydroxy-2-(1-methyl-1-phenylethyl)-2,3-dihydro-1H-isoindol-1-one
  参考文献：
  名称：

  N-Cumyl Benzamide, Sulfonamide, and Aryl O-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics

  摘要：

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.

  DOI：

  10.1021/ol990846b

文献信息

• The Behavior of 2-Substituted-3-hydroxyisoindolinones in the Reaction with<i>sec</i>-Butyllithium
  作者：A. Jóźwiak、M. Ciechańska

  DOI：10.1002/jhet.1636

  日期：2014.3

  This paper presents a dualistic behavior of 2‐substituted‐3‐hydroxyisoindolones in reactions with sec‐butyllithium (sec‐BuLi). 2‐tert‐Butyl‐3‐hydroxy‐2,3‐dihydro‐1H‐isoindol‐1‐one (1a) treated with sec‐BuLi undergoes metalation at position 7. On the other hand, the reaction between 3‐hydroxy‐2‐phenyl‐2,3‐dihydroxyisoindol‐1‐one (1j) and sec‐BuLi results in 3‐sec‐butyl‐2‐phenyl‐2,3‐dihydroisiondol‐1‐one

  本文介绍了2-取代-3-羟基异吲哚酮与仲丁基锂（sec - BuLi ）的对偶行为。用sec- BuLi处理的2-叔丁基-3-羟基-2,3-二氢-1 H-异吲哚-1-酮（1a）在位置7发生金属化。另一方面，3-羟基-羟基之间的反应2-苯基-2-3,3-二羟基异吲哚-1-酮（1j）和sec- BuLi生成3- sec-丁基-2-苯基-2-3,2-二氢碘吲哚-1-酮（3j）。
• A BF₃-Mediated Nitrogen-to-Carbon Rearrangement of N-Protected 2,3-Dihydro-3-hydroxy-1<i>H</i>-benzisoindol-1-ones, and Its Interception for a Facile Preparation of 3-Substituted Benzisoindolones
  作者：Adrian Schwan、Petar Duspara、Michelle Paquette、A. Merrill

  DOI：10.1055/s-2006-951495

  日期：2006.11

  accompanied by recombination of the nitrogen-protecting unit to the 3-position of the ring system. The addition of sulfur or carbon nucleophiles affords products of preferential capture of the rearrangement intermediate offering a convenient and rapid synthetic route to N-unprotected 2,3-dihydro-3-substituted-1H-benzisoindol-1-ones.

  BF 3 介导的 N-(枯基或 1,1-二苯基乙基)-2,3-二氢-3-羟基-1H-苯并异吲哚-1-酮的羟基和氮保护基团的释放伴随着将氮保护单元连接到环系统的 3 位。硫或碳亲核试剂的添加提供了重排中间体的优先捕获产物，为 N-未保护的 2,3-二氢-3-取代-1H-苯并异吲哚-1-酮提供了方便快捷的合成途径。
• Nitrogen-containing heterocyclic compound
  申请人：Murakata Chikara

  公开号：US20090054407A1

  公开（公告）日：2009-02-26

  The present invention provides a nitrogen-containing heterocyclic compound represented by formula (I): wherein W represents a nitrogen atom or —CH—; X represents —C(═O)— or —CHR 4 — (wherein R 4 represents a hydrogen atom, or the like); R 1 represents a group represented by the following formula: [wherein Q 1 represents a nitrogen atom or —CR 8 — (wherein R 8 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like). Q 2 represents —NR 15 — (wherein R 15 represents a hydrogen atom, or the like) and R 5 and R 6 may be the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like]; and R 2 and R 3 may be the same or different and each represents a hydrogen atom, halogen, substituted or unsubstituted lower alkyl, or the like} or a pharmaceutically acceptable salt thereof, and the like.

  本发明提供了一种含氮杂环化合物，其由式(I)表示：其中W代表氮原子或—CH—；X代表—C(═O)—或—CHR4—（其中R4代表氢原子或类似物）；R1代表由以下式表示的基团：[其中Q1代表氮原子或—CR8—（其中R8代表氢原子、取代或未取代的低级烷基或类似物）。Q2代表—NR15—（其中R15代表氢原子或类似物），R5和R6可以相同也可以不同，每个代表氢原子、取代或未取代的低级烷基或类似物]；R2和R3可以相同也可以不同，每个代表氢原子、卤素、取代或未取代的低级烷基或类似物}或其药学上可接受的盐等。
• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1880993A1

  公开（公告）日：2008-01-23

  The present invention provides a nitrogen-containing heterocyclic compound represented by formula (I): wherein W represents a nitrogen atom or -CH-; X represents -C(=O)- or -CHR4- (wherein R4 represents a hydrogen atom, or the like); R1 represents a group represented by the following formula: [wherein Q1 represents a nitrogen atom or -CR8- (wherein R8 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like), Q2 represents -NR15- (wherein R15 represents a hydrogen atom, or the like) and R5 and R6 may be the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like]; and R2 and R3 may be the same or different and each represents a hydrogen atom, halogen, substituted or unsubstituted lower alkyl, or the like } or a pharmaceutically acceptable salt thereof, and the like.

  本发明提供了一种由式（I）表示的含氮杂环化合物： 其中 W 代表氮原子或-CH-； X代表-C(＝O)-或-CHR4-（其中R4代表氢原子或类似物）； R1 代表下式所代表的基团： [其中 Q1 代表氮原子或-CR8-（其中 R8 代表氢原子、取代或未取代的低级烷基或类似物），Q2 代表-NR15-（其中 R15 代表氢原子或类似物），R5 和 R6 可以相同或不同，各自代表氢原子、取代或未取代的低级烷基或类似物]；以及 R2 和 R3 可以相同或不同，各自代表氢原子、卤素、取代或未取代的低级烷基或类似物 } 或其药学上可接受的盐等。
• US7745641B2
  申请人：——

  公开号：US7745641B2

  公开（公告）日：2010-06-29