(1Z)-5,7-dichloro-3-(cyclohexylimino)-1-[(6,8-dichloro-4-oxo-4H-chromen-3-yl)methylene]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1Z)-5,7-dichloro-3-(cyclohexylimino)-1-[(6,8-dichloro-4-oxo-4H-chromen-3-yl)methylene]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one
• 英文别名: (1Z)-5,7-dichloro-3-cyclohexylimino-1-[(6,8-dichloro-4-oxochromen-3-yl)methylidene]furo[3,4-b]chromen-9-one
• 化学式: C₂₇H₁₇Cl₄NO₅
• 分子量: 577.248
• InChiKey: QBUCBSOYRBKQGN-XNWDSMPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异氰环已烷 、 6,8-二氯-3-甲酰色酮 在 甲醇 、 四氯苯二甲酸酐 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (1Z)-5,7-dichloro-3-(cyclohexylimino)-1-[(6,8-dichloro-4-oxo-4H-chromen-3-yl)methylene]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one
  参考文献：
  名称：

  烷基的四分量合成[2 - [（环己基氨基）羰基] -4-氧代-2- ħ -色烯-3（4 ħ） -亚基]甲基-3,4,5,6- tetrahalophthalates经由一个多米诺Ô酰化/ α-加成环化/醇解序列

  摘要：

  一种新的协议是为烷基的合成开发[2 - [（环己基氨基）羰基] -4-氧代-2- ħ -色烯-3（4 ħ） -亚基]甲基-3,4,5,6- tetrahalophthalate衍生物经由所述四卤代邻苯二甲酸酐，3-甲酰基色酮，环己基异氰化物和各种醇的一锅四组分多米诺骨牌O-酰化/α-加成环化/醇解反应。这种新颖的级联反应的亮点包括温和的反应条件，容易的后处理和高的键合效率，导致在一次操作中形成四个新键（两个C O，一个C O和一个C C）。

  DOI：

  10.1016/j.tetlet.2018.02.037

文献信息

• Four-component synthesis of alkyl [2-[(cyclohexylamino)carbonyl]-4-oxo-2H-chromen-3(4H)-ylidene]methyl 3,4,5,6-tetrahalophthalates via a domino O-acylation/α-addition cyclization/alcoholysis sequence
  作者：Mohammad Bagher Teimouri、Sahar Inanloo

  DOI：10.1016/j.tetlet.2018.02.037

  日期：2018.3

  A novel protocol was developed for the synthesis of alkyl [2-[(cyclohexylamino)carbonyl]-4-oxo-2H-chromen-3(4H)-ylidene]methyl 3,4,5,6-tetrahalophthalate derivatives via the one-pot, four-component domino O-acylation/α-addition cyclization/alcoholysis reaction of tetrahalophthalic anhydrides, 3-formylchromones, cyclohexyl isocyanide and various alcohols. The highlights of this novel cascade reaction

  一种新的协议是为烷基的合成开发[2 - [（环己基氨基）羰基] -4-氧代-2- ħ -色烯-3（4 ħ） -亚基]甲基-3,4,5,6- tetrahalophthalate衍生物经由所述四卤代邻苯二甲酸酐，3-甲酰基色酮，环己基异氰化物和各种醇的一锅四组分多米诺骨牌O-酰化/α-加成环化/醇解反应。这种新颖的级联反应的亮点包括温和的反应条件，容易的后处理和高的键合效率，导致在一次操作中形成四个新键（两个C O，一个C O和一个C C）。
• Reaction between alkyl isocyanides and 3-formylchromones in the presence of monocyclic unsaturated acyl compounds: Competition between Friedel-Crafts acylation and Diels-Alder cycloaddition
  作者：Mohammad Bagher Teimouri、Shabnam Mohammadnia

  DOI：10.1016/j.tet.2018.01.054

  日期：2018.4

  from the reaction between 3-formylchromones and alkyl isocyanides, was trapped by monocyclic unsaturated acyl compounds such as maleic anhydride or maleimide derivatives to yield new types of organic fluorophores 4-(alkylamino)-1H-furo[3,4-b]xanthene-1,3,10-triones or 4-(alkylamino)chromeno[2,3-f]isoindole-1,3,10(2H)-triones, which exhibited strong sky blue emission in solution. The reaction is very

  由3-甲酰基色酮与烷基异氰化物反应生成的高反应性烷基氨基呋喃色酮中间体被单环不饱和酰基化合物（例如马来酸酐或马来酰亚胺衍生物）捕获，从而产生新型的有机荧光团4-（烷基氨基）-1 H-呋喃[ 3,4- b ]黄嘌呤-1,3,10-三酮或4-（烷基氨基）铬色[2,3 - f ]异吲哚-1,3,10（2 H）-三酮，在室温下表现出较强的天蓝色发射。解决方案。从实验的角度来看，该反应非常简单，并允许在一次操作中形成稠合的苯环，并伴随形成三个新的C–C键。
• Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit
  作者：Mohammad Teimouri、Bita Asnaashari、Maryam Moayedi、Soheila Naderi

  DOI：10.1055/s-0034-1378926

  日期：——

  A diastereoselective synthesis of highly substituted succinimide derivatives with chromone and carboxylic ester functionalities from 3-formylchromones, Meldrum's acid, and alkyl isocyanides in the presence of alcohols in moderate to good yields is described.
• Serendipitous stereoselective synthesis of brand-new fluorescent dyes: (1Z)-3-(alkylimino)-1-[(chromone-3-yl)methylene]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one-type fluorophores with blue fluorescence emission properties
  作者：Mohammad Bagher Teimouri

  DOI：10.1016/j.tet.2011.01.033

  日期：2011.3

  The reactions of 3-formylchromones with alkyl isocyanides in dry dichloromethane at room temperature lead to new types of organic fluorophores (1Z)-3-(alkylimino)-1-[(chromone-3-yl)methylene]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one, which exhibited strong blue emission in solution. The reactions involve a [4+1] cycloaddition followed by an activated electrophilic aromatic substitution at the furan ring and dehydration sequence. (C) 2011 Elsevier Ltd. All rights reserved.
• Combining cycloaddition reactions for the one-pot synthesis of novel xanthoquinone dyes
  作者：Mohammad Bagher Teimouri、Zahra Bozorgpour Savadjani、Morteza Shiri、Rahman Bikas、Soheila Naderi

  DOI：10.1016/j.dyepig.2022.110106

  日期：2022.3

  generated in situ from the corresponding chromone-3-carbaldehyde and alkyl or aryl isocyanide via a formal [4 + 1] cycloaddition reaction, then engaged by p-quinone partner (1,4-benzoquinone or 1,4-naphthoquinone) as an electron-deficient dienophile to afford the desired novel xanthoquinone dye via a [4 + 2] cycloaddition/ring opening/dehydrative aromatization sequence.

  已合成了由黄酮和醌亚基组成的一类新型醌染料黄醌。一种难以捉摸的氨基呋喃色酮作为富电子二烯，由相应的色酮-3-甲醛和烷基或芳基异氰化物通过形式 [4 + 1] 环加成反应原位生成，然后与对醌配对物 (1,4-苯醌或 1,4-萘醌）作为缺电子双烯体，通过[4 + 2] 环加成/开环/脱水芳构化序列提供所需的新型黄醌染料。