2-(2-methylprop-1-enyl)-2-benzazole-1,3-dione | 73286-68-7

• 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: 2-(2-methylprop-1-enyl)-2-benzazole-1,3-dione
• 英文别名: 2-(2'-methylprop-1'-enyl)-2-benzazoline-1,3-dione；2-(2-methylprop-1-en-1-yl)isoindoline-1,3-dione；2-(2-Methyl-prop-1-enyl)-isoindole-1,3-dione；2-(2-methylprop-1-enyl)isoindole-1,3-dione
• CAS: 73286-68-7
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: YQZAKMGKXXCWOK-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solv: hexane (110-54-3))
• 沸点：
  332.9±25.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-酞酰亚胺基-3-甲基丁酸 在 氯化亚砜 作用下， 以 neat (no solvent) 为溶剂， 反应 7.0h， 生成 2-(2-methylprop-1-enyl)-2-benzazole-1,3-dione
  参考文献：
  名称：

  基于手性池的萘酚异香豆素合成

  摘要：

  通过Et 3 N介导的高邻苯二甲酸酐与（S）-氨基酸氯化物不同衍生物的缩合反应一步一步制备了各种苯并[d]萘[1,2-b]吡喃-6-酮的手性衍生物通过使用手性池方法在–5°C下进行。手性27：951–957，2015。©2015 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22530

文献信息

• Photochemistry of phthaloylcysteine, its methyl ester and C-unprotected S-alkyl derivatives
  作者：Axel G. Griesbeck、Joachim Hirt、Wolfgang Kramer、Paul Dallakian

  DOI：10.1016/s0040-4020(98)00063-5

  日期：1998.3

  cysteine derivatives 1a-d were photochemically transformed by elimination, decarboxylation, and via electron transfer cyclization to the products 2,3,4 and 6–8. The spin selectivities of singlet and triplet pathways were investigated in acetonitrile and acetone. The excited singlets were prone to elimination and γ-H abstractions (e.g. formation of 5) whereas the triplets cyclized to thiazinoisoindoles

  N-邻苯二甲酰基半胱氨酸衍生物1a-d通过消除，脱羧和通过电子转移环化而光化学转化为产物2,3,4和6-8。在乙腈和丙酮中研究了单重态和三重态途径的自旋选择性。激发的单线态易于消除和γ-H提取（例如形成5），而三联体环化成噻嗪基异吲哚。该行为可以与正向和返回电子转移步骤相对于均质氢提取的效率相关，如半胱氨酸底物9所证明的。
• Pd-Catalyzed Tandem Isomerization/Cyclization for the Synthesis of Aromatic Oxazaheterocycles and Pyrido[3,4-<i>b</i>]indoles
  作者：Linglong Ding、Yan-Ning Niu、Xiao-Feng Xia

  DOI：10.1021/acs.joc.1c00770

  日期：2021.8.6

  An effient tandem process consisting of palladium-catalyzed double-bond isomerization of long-chain olefins and subsequent intramolecular cyclization promoted by B2(OH)2 for the synthesis of aromatic oxazaheterocycles is disclosed. This strategy can also provide rapid access to pyrido[3,4-b]indoles, trans-2-olefins, and eneamides bearing various functional groups with high regio- and stereoselectivity

  公开了一种由钯催化的长链烯烃双键异构化和随后由 B 2 (OH) 2促进的分子内环化合成芳族氧杂杂环的有效串联方法。该策略还可以快速获得具有高区域和立体选择性的各种官能团的吡啶并[3,4- b ]吲哚、反式-2-烯烃和烯酰胺。
• Hydrocarbonylation of unsaturated nitrogen compounds. Synthesis of N-protected aminoacid derivatives from N-substituted phthalimides
  作者：Giovanna Delogu、Giovanni Faedda、Serafino Gladiali

  DOI：10.1016/0022-328x(84)80244-2

  日期：1984.6

  The hydrocarbonylation of some β-substituted N-vinylphthalimides catalysed by Rh or Pd complexes has been investigated. The reaction is strongly affected by the nature of the substituent and is completely prevented when two substituents are present. The addition of carbon monoxide, when it occurs, takes place with complete selectivity and its direction can be regulated to a large extent by selecting

  研究了Rh或Pd配合物催化的一些β-取代的N-乙烯基邻苯二甲酰亚胺的烃基化反应。该反应受取代基性质的强烈影响，当存在两个取代基时，反应被完全阻止。一氧化碳的发生完全选择性地发生，并且通过选择反应参数可以在很大程度上调节其方向。
• Isomerization of N-allylamides and -imides to aliphatic enamides by iron, rhodium, and ruthenium complexes
  作者：J. K. Stille、Y. Becker

  DOI：10.1021/jo01299a021

  日期：1980.5
• Chiron based synthesis of isocoumarins: reactivity of α-substituted carboxylic acids
  作者：Aisha Saddiqa、Abdul R. Raza、David StC. Black、Naresh Kumar

  DOI：10.1016/j.tetasy.2014.03.019

  日期：2014.5

  The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and alpha-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with alpha-chloro-acids afforded asymmetric isocoumarins in high yield. (C) 2014 Elsevier Ltd. All rights reserved.