2',6'-dimethyl-4'-benzyloxycarbonylphenyl 3-(4-methoxystyrenyl)-acridine-9-carboxylate | 259169-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2',6'-dimethyl-4'-benzyloxycarbonylphenyl 3-(4-methoxystyrenyl)-acridine-9-carboxylate
• 英文别名: (2,6-dimethyl-4-phenylmethoxycarbonylphenyl) 3-[(E)-2-(4-methoxyphenyl)ethenyl]acridine-9-carboxylate
• CAS: 259169-21-6
• 化学式: C₃₉H₃₁NO₅
• 分子量: 593.679
• InChiKey: MITLFXDFHMOGRF-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.72
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2',6'-dimethyl-4'-carboxybenzylphenyl acridine-9-carboxylate-3-carboxaldehyde 、 (4-甲氧基苄基)三苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 2',6'-dimethyl-4'-benzyloxycarbonylphenyl 3-(4-methoxystyrenyl)-acridine-9-carboxylate
  参考文献：
  名称：

  Near infrared chemiluminescent acridinium compounds and uses thereof

  摘要：

  本申请涉及具有电子给体基团的长波长蒽醌化合物，该电子给体基团可以是：（a）作为扩展的共轭系统的一部分，通过适当的功能基团连接到蒽醌核上，发光过程中附加功能基团和蒽酮基团保持共面性（几何要求），所述功能基团包括至少一个芳环和一个具有额外电子对的电子给体原子或基团，该电子对可以很容易地共享到直接连接或内置到杂原子所在的扩展π系统中，并与发光蒽酮的电子受体羰基基团建立稳定的扩展共振。如果该电子给体原子或基团以阴离子的形式存在，则特别强烈地影响向长波长方向的发射波长的巴托克移；或（b）直接连接到蒽醌核的C-2、C-4、C-5或C-7位置之一或多个上，具有额外电子对的电子给体原子或基团。如果使用多个电子给体实体，则这些电子给体实体可以相同或不同。以阴离子形式存在的电子给体原子或基团特别强烈地影响向长波长方向的发射波长的巴托克移。

  公开号：

  US06355803B1

文献信息

• NEAR INFRARED CHEMILUMINESCENT ACRIDINIUM COMPOUNDS AND USES THEREOF
  申请人：Bayer Corporation

  公开号：EP1104405A1

  公开（公告）日：2001-06-06
• US6355803B1
  申请人：——

  公开号：US6355803B1

  公开（公告）日：2002-03-12
• US7083986B2
  申请人：——

  公开号：US7083986B2

  公开（公告）日：2006-08-01
• US7611909B1
  申请人：——

  公开号：US7611909B1

  公开（公告）日：2009-11-03
• [EN] NEAR INFRARED CHEMILUMINESCENT ACRIDINIUM COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSES D'ACRIDINIUM CHIMILUMINESCENTS DANS LE PROCHE INFRAROUGE ET SES UTILISATIONS
  申请人：BAYER AG

  公开号：WO2000009487A1

  公开（公告）日：2000-02-24

  Our results thus identify two sets of necessary and sufficient criteria for observing long-wavelength emission from acridinium compounds: Set A: (a) the creation of an extended conjugation system by the attachment of appropriate functional groups on the acridinium nucleus (electronic requirement). (b) Coplanarity of the attached functional group and the acridone moiety during light emission (geometry requirement). (c) Said functional group must consist of at least one aromatic ring and one electron-donating atom or group with an extra pair of electrons which can readily delocalize into the extended π system to which the heteroatom is directly attached or built into, and establish stable extended resonance with the electron-withdrawing carbonyl moiety of the light emitting acridone. Such electron-donating atom or group that exists in the form of an anion has particularly strong effect to further the bathochromic shift of the emission wavelength. Set B: (a) A direct attachment at one or more of positions C-2, C-4, C-5, or C-7 of the acridinium nucleus, of electron-donating atoms or groups having extra pair(s) of electrons. The electron-donating entities can be the same or different if more than one electron-donating entity is used. Such electron-donating atom or group that exists in the form of an anion has particularly strong effect to further the bathochromic shift of the emission wavelenth. For molecules for which the above criteria are met such as LEAE, 3-HS-DMAE, and 2-hydroxy-DMAE long wavelength-emission exceeding 500 nm and reaching into NIR region is expected and observed. Preferably, the utility of an NIR-AC of comparable quantum yield as the conventional acridinium compounds goes hand-in-hand with the employment of a luminescence detector of good to excellent detection efficiency. To achieve efficient NIR signal detection and facilitate the performing of diagnostic assays, a further objective of the present invention is the advance of a concept and the realization of substituting a state-of-the-art charge-coupled device (CCD) detector for the red-insensitive photomultiplier tube (PMT) in a conventional fully or semi-automatic analyzer such as MLA-II of Chiron Diagnostics, Walpole, MA.