diethyl 12-(2-acetyloxyethenyl)-2,2-difluoro-4-methyl-6,10-diphenyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5,11-dicarboxylate | 1206782-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 12-(2-acetyloxyethenyl)-2,2-difluoro-4-methyl-6,10-diphenyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5,11-dicarboxylate
• CAS: 1206782-13-9
• 化学式: C₃₂H₂₉BF₂N₂O₆
• 分子量: 586.4
• InChiKey: YFTAECGRVCYSCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  diethyl 12-(2-acetyloxyethenyl)-2,2-difluoro-4-methyl-6,10-diphenyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5,11-dicarboxylate 在 哌啶 、 sodium acetate 、 溶剂黄146 作用下， 以 氯仿 、 异丙醇 、 苯 为溶剂， 反应 4.0h， 生成 2-carbethoxy-3-styryl-7-(1-butyl)-1,9-diphenyl-4,4-difluoro-3a,4a,7-triaza-4-bora-cyclopenta[b]fluoren-8-one
  参考文献：
  名称：

  An efficient method of chemical modification of BODIPY core

  摘要：

  A simple approach to the modification of BODIPY nucleus has been developed. The method is based on the reaction of acetaldehyde-substituted dye with primary amines followed by cyclization of enamine intermediates. This procedure allowed preparing a series of new BODIPY derivatives with functional substituents useful for various practical purposes, including bioconjugation and other biomedical applications. The synthesized BODIPYs annealed to a pyridone fragment are stable compounds and intense fluorophores with emission maximum around 615 nm. This lambda(em) may be red-shifted by the introduction of styryl substituent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.050

文献信息

• Preparation, Characterization, Redox, and Photoinduced Electron‐Transfer Properties of the NIR‐Absorbing <i>N</i> ‐Ferrocenyl‐2‐pyridone BODIPYs
  作者：Yuriy V. Zatsikha、Natalia O. Didukh、Tanner Blesener、Mathew P. Kayser、Yuriy P. Kovtun、David A. Blank、Victor N. Nemykin

  DOI：10.1002/ejic.201600855

  日期：2017.1.10

  coupling between the two ferrocene groups. Oxidation of the ferrocene(s) in the target BODIPYs results in their observable fluorescence, while transient absorption spectroscopy data indicate fast electron-transfer from ferrocene donor to the photoexcited BODIPY acceptor. Density functional theory (DFT) and time-dependent DFT (TDDFT) methods were used to elucidate electronic structures of the organometallic

  使用一组二茂铁 - 烯胺环化反应制备含有单和二（N-二茂铁基-2-吡啶酮）的 BODIPY。目标化合物通过紫外-可见光谱、核磁共振和质谱进行表征，同时通过电化学、光谱电化学和化学氧化方法探测它们的氧化还原特性。含二（二茂铁）的 BODIPY 的氧化还原特性表明两个二茂铁基团之间缺乏电子耦合。目标 BODIPY 中二茂铁的氧化导致它们可观察到的荧光，而瞬态吸收光谱数据表明从二茂铁供体到光激发的 BODIPY 受体的快速电子转移。
• 3,5-Bis(acetaldehyde) substituted BODIPY
  作者：Mykola P. Shandura、Viktor P. Yakubovskyi、Yuriy P. Kovtun

  DOI：10.1039/c2ob27004h

  日期：——

  synthetic approach to 3,5-bis(acetaldehyde) substituted BODIPY have been developed and this compound has been used to obtain, in high yields, a variety of 3,5-divinyl BODIPY derivatives (vinylacetates, enamines, vinyl chlorides, and some multiple-functionalized products). As shown, vinyl substituents have an additive effect on the position of the BODIPY absorption maximum. The dyes synthesized are quite

  已经开发出两种简便有效的合成方法来合成3,5-双（乙醛）取代的BODIPY，并且该化合物已用于高收率地获得各种3,5-二乙烯基BODIPY衍生物（醋酸乙烯酯，烯胺，氯乙烯和某些多功能产品）。如图所示，乙烯基取代基对BODIPY吸收最大值的位置具有加和作用。合成的染料非常稳定，在波长大于600 nm时表现出强烈的吸收和荧光。