(E)-3-benzylideneisoindolin-1-one | 33608-93-4

• 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: (E)-3-benzylideneisoindolin-1-one
• 英文别名: (3E)-3-benzylideneisoindol-1-one
• CAS: 33608-93-4
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: ICCBGFWJTALFFU-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-benzylideneisoindolin-1-one 在 air 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 3-(phenylmethylene)isoindol-1-one
  参考文献：
  名称：

  Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

  摘要：

  Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.017
• 作为产物：
  描述：

  2,3-dihydro-3-hydroxy-3-(phenylmethyl)-1H-isoindol-1-one 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(E)-3-benzylideneisoindolin-1-one
  参考文献：
  名称：

  Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

  摘要：

  Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.017

文献信息

• Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides
  作者：Feng Xiong、Bo Li、Chenrui Yang、Liang Zou、Wenbo Ma、Linghui Gu、Ruhuai Mei、Lutz Ackermann

  DOI：10.3762/bjoc.17.113

  日期：——

  The efficient copper-mediated oxidative C–H alkynylation of benzhydrazides was accomplished with terminal alkynes. Thus, a heteroaromatic removable N-2-pyridylhydrazide allowed for domino C–H/N–H functionalization. The approach featured remarkable functional group compatibility and ample substrate scope. Thereby, highly functionalized aromatic and heteroaromatic isoindolin-1-ones were accessed with high efficacy with rate-limiting C–H cleavage.

  直接给您结果：

  通过铜催化的高效氧化C-H炔基化反应，使用末端炔烃成功实现了对苯基肼的反应。因此，一种杂环可拆卸的N-2-吡啶基肼允许进行多米诺C-H/N-H官能团化反应。该方法具有显著的官能团兼容性和广泛的底物范围。因此，高度官能化的芳香族和杂环异吲哚啉-1-酮可以以高效率获得，其速率限制步骤为C-H断裂。

• Photo-Induced Sonogashira CC Coupling Reaction Catalyzed by Simple Copper(I) Chloride Salt at Room Temperature
  作者：Arunachalam Sagadevan、Kuo Chu Hwang

  DOI：10.1002/adsc.201200683

  日期：2012.12.14

  conventional thermal Sonogashira CC coupling reaction requires the use of a palladium catalyst and a large amount of ligands. Although there were a few reports describing the use of inexpensive metal catalysts, such as, copper (Cu), iron (Fe), and nickel (Ni), for replacement of palladium (Pd) in the Sonogashira reactions, it was later questioned that the observed effects were due to ppb levels contamination

  常规的热Sonogashira CC偶联反应需要使用钯催化剂和大量的配体。尽管有一些报道描述了在Sonogashira反应中使用廉价的金属催化剂，例如铜（Cu），铁（Fe）和镍（Ni）替代钯（Pd），但后来有人质疑说观察到的效果是由于反应所用试剂中ppb含量的Pd污染所致。在本文中，我们报道，在室温下，在蓝色LED光照射下，简单的氯化铜（I）氯化铜（CuCl）盐在没有Pd和配体的情况下可以高产率（80-99％）催化Sonogashira反应。对照实验表明，当氯化钯（II）（PdCl 2）被用来代替CuCl作为催化剂。研究了一系列富电子和贫电子的取代的芳基卤化物（溴化物和碘化物）以及芳基和烷基乙炔，并讨论了反应机理。
• Cobalt(II)‐Catalyzed CH Alkynylation/Annulation with Terminal Alkynes: Selective Access to 3‐Methyleneisoindolin‐1‐one
  作者：Lin‐Bao Zhang、Xin‐Qi Hao、Zhan‐Jiang Liu、Xin‐Xiang Zheng、Shou‐Kun Zhang、Jun‐Long Niu、Mao‐Ping Song

  DOI：10.1002/anie.201504962

  日期：2015.8.17

  A highly efficient cobalt(II)‐catalyzed alkynylation/annulation of terminal alkynes assisted by an N,O‐bidentate directing group is described. This protocol is characterized by wide substrate scope utilizing cheap cobalt catalysts, and offers a new approach to 3‐methyleneisoindolin‐1‐one, which can be converted into an oxadiazine salt in one step. Moreover, the directing group could be removed in three

  描述了一种高效的钴（II）催化的炔基化/环炔反应，由N，O-双齿定向基团协助。该协议的特点是使用廉价的钴催化剂可扩大底物范围，并为3-亚甲基异吲哚啉-1-酮提供了一种新方法，可将其一步转化为恶二嗪盐。此外，可以通过三个步骤删除指导组。
• Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction
  作者：Scott A. Shuler、Guoyin Yin、Sarah B. Krause、Caroline M. Vesper、Donald A. Watson

  DOI：10.1021/jacs.6b08932

  日期：2016.10.26

  The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

  报道了通过钯催化的邻苯基异羟肟酸酯环化到侧链烯烃上制备不饱和仲内酰胺。这种方法提供了对广泛范围内的内酰胺的快速访问，这些内酰胺是生物碱合成中广泛有用的组成部分。机制研究支持 aza-Heck 型途径。
• Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones
  作者：Naoki Kise、Yusuke Kawano、Toshihiko Sakurai

  DOI：10.1021/jo402125u

  日期：2013.12.20

  The reductive coupling of phthalimides with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydroxy-3-(1-hydroxyalkyl)isoindolin-1-ones and alkylideneisoindolin-1-ones, selectively by controlling the reaction conditions. Therefore, the one-pot synthesis of alkylideneisoindolin-1-ones from phthalimides was effected by this reaction. Although the alkylideneisoindolin-1-ones

  Zn-TiCl 4在THF中将邻苯二甲酰亚胺与酮和醛还原偶联，可选择性地产生两电子还原产物和三电子还原产物3-羟基-3-（1-羟烷基）异吲哚啉-1-酮和亚烷基异异吲哚-1-酮。通过控制反应条件。因此，通过该反应实现了由邻苯二甲酰亚胺的一锅法合成亚烷基异吲哚啉-1-酮。尽管在大多数情况下，由邻苯二甲酰亚胺和醛制得的亚烷基异二氢吲哚-1-酮是作为几何异构体的混合物形成的，但在猫体内通过回流可以提高几何比。PPTS /甲苯。异构化后，N-甲基取代的亚烷基亚异吲哚啉-1-酮（X = Me，R 1 = R，R 2 = H）的E-异构体优先获得N-未取代的亚烷基亚异吲哚啉-1-酮（X ＝ H，R 1＝ H，R 2＝ R）的Z-异构体。