4,4-difluoro-8-(2-aminophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-difluoro-8-(2-aminophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 2-(2,2-Difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)aniline；2-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)aniline
• 化学式: C₁₉H₂₀BF₂N₃
• 分子量: 339.196
• InChiKey: LZLXAWGKHOGTBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  马来酸酐 、 4,4-difluoro-8-(2-aminophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 以 溶剂黄146 为溶剂， 反应 3.5h， 以100%的产率得到10-(2-(3-carboxyacrylamido)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  NOVEL MALEIMIDE DERIVATIVE

  摘要：

  由以下一般式（I）表示的化合物：[其中R1和R2分别表示氢原子，或由以下式（A）表示的基团：（其中X1和X2表示氢原子、烷基基团、烷氧基团或卤素原子），条件是R1和R2不同时表示氢原子；R3和R6表示烷基基团；R4和R7表示氢原子、烷基基团、羧基、烷氧羰基或磺酰基；R5和R8表示烷基基团、芳基、烷氧羰基、乙烯基、噻吩基或吡咯基]，或其盐，可用于高效筛选具有作为迈克尔加成反应催化剂适用性的化学物质。

  公开号：

  US20090318707A1
• 作为产物：
  描述：

  2,4-二甲基吡咯 在 nickel(II) chloride hexahydrate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.91h， 生成 4,4-difluoro-8-(2-aminophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Live Cell Labeling of Native Intracellular Bacterial Receptors Using Aniline-Catalyzed Oxime Ligation

  摘要：

  Live cell fluorescent labeling of proteins has become a seminal tool in biology and has led to hallmark discoveries in diverse research areas such as protein trafficking, cell-to-cell interactions, and intracellular network dynamics. One of the main challenges, however, remains the ability to label intracellular proteins using fluorescent ligands with high specificity, all the while retaining viability of the targeted cells. Here, we present the first example of live cell labeling and imaging of an intracellular bacterial receptor involved in cell-to-cell communication (i.e., quorum sensing), using a novel two-step approach involving covalent attachment of a reactive mimic of the primary endogenous Pseudomonas aeruginosa quorum-sensing signal to its receptor, LasR, followed by aniline-catalyzed mime formation between the modified receptor and a fluorescent BODIPY derivative. Our results indicate that LasR is not distributed evenly throughout the cytoplasmic membrane but is instead concentrated at the poles of the P. aeruginosa cell.

  DOI：

  10.1021/ja200455d

文献信息

• Design and Synthesis of a Library of BODIPY-Based Environmental Polarity Sensors Utilizing Photoinduced Electron-Transfer-Controlled Fluorescence ON/OFF Switching
  作者：Hisato Sunahara、Yasuteru Urano、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ja068551y

  日期：2007.5.1

  We systematically examined the mechanism of the solvent polarity dependence of the fluorescence ON/OFF threshold of the BODIPY (boron dipyrromethene) fluorophore and the role of photoinduced electron transfer (PeT). In a series of BODIPY derivatives with variously substituted benzene moieties at the 8-position, the oxidation potential of the benzene moiety became more positive and the reduction potential of the BODIPY fluorophore became more negative as the solvent polarity was decreased; consequently, the free energy change of PeT from the benzene moiety becomes larger in a more nonpolar environment. Utilizing this finding, we designed and synthesized a library of probes in which the threshold of fluorescence ON/OFF switching corresponds to different levels of solvent polarity. These environment-sensitive probes were used to examine bovine serum albumin (BSA) and living cells. The polarity at the surface of albumin was concluded to be similar to that of acetone, while the polarity of the internal membranes of HeLa cells was similar to that of dichloromethane.
• NOVEL MALEIMIDE DERIVATIVE
  申请人：Matsumoto Takuya

  公开号：US20090318707A1

  公开（公告）日：2009-12-24

  A compound represented by the following general formula (I): [wherein R 1 and R 2 independently represent hydrogen atom, or a group represented by the following formula (A): (wherein X 1 and X 2 represent hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom), provided that R 1 and R 2 do not simultaneously represent hydrogen atom; R 3 and R 6 represent an alkyl group; R 4 and R 7 represent hydrogen atom, an alkyl group, carboxy group, an alkoxycarbonyl group, or sulfo group; and R 5 and R 8 represents an alkyl group, an aryl group, an alkoxycarbonyl group, a vinyl group, a thienyl group, or a pyrrolyl group], or a salt thereof, which is usable for efficient screening for a chemical substance having applicability as a catalyst of the reaction of Michael addition.

  由以下一般式（I）表示的化合物：[其中R1和R2分别表示氢原子，或由以下式（A）表示的基团：（其中X1和X2表示氢原子、烷基基团、烷氧基团或卤素原子），条件是R1和R2不同时表示氢原子；R3和R6表示烷基基团；R4和R7表示氢原子、烷基基团、羧基、烷氧羰基或磺酰基；R5和R8表示烷基基团、芳基、烷氧羰基、乙烯基、噻吩基或吡咯基]，或其盐，可用于高效筛选具有作为迈克尔加成反应催化剂适用性的化学物质。
• Live Cell Labeling of Native Intracellular Bacterial Receptors Using Aniline-Catalyzed Oxime Ligation
  作者：Josep Rayo、Neri Amara、Pnina Krief、Michael M. Meijler

  DOI：10.1021/ja200455d

  日期：2011.5.18

  Live cell fluorescent labeling of proteins has become a seminal tool in biology and has led to hallmark discoveries in diverse research areas such as protein trafficking, cell-to-cell interactions, and intracellular network dynamics. One of the main challenges, however, remains the ability to label intracellular proteins using fluorescent ligands with high specificity, all the while retaining viability of the targeted cells. Here, we present the first example of live cell labeling and imaging of an intracellular bacterial receptor involved in cell-to-cell communication (i.e., quorum sensing), using a novel two-step approach involving covalent attachment of a reactive mimic of the primary endogenous Pseudomonas aeruginosa quorum-sensing signal to its receptor, LasR, followed by aniline-catalyzed mime formation between the modified receptor and a fluorescent BODIPY derivative. Our results indicate that LasR is not distributed evenly throughout the cytoplasmic membrane but is instead concentrated at the poles of the P. aeruginosa cell.