N-[3-(4-benzyloxyphenyl)phenyl]isatin | 259169-38-5

• 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: N-[3-(4-benzyloxyphenyl)phenyl]isatin
• 英文别名: 1-[3-(4-phenylmethoxyphenyl)phenyl]indole-2,3-dione
• CAS: 259169-38-5
• 化学式: C₂₇H₁₉NO₃
• 分子量: 405.453
• InChiKey: NOJZGLFQHCMVQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 、 sodium;hydride 、 4'-Benzyloxy-3-bromo-biphenyl 在 cupric iodide ice 、 氮 、 乙酸乙酯 、 silica gel 、 hexanes 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 N-[3-(4-benzyloxyphenyl)phenyl]isatin
  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腺嘌呤化合物，其可以是：（a）作为一个扩展的共轭系统的一部分，通过适当的功能基团连接到腺嘌呤核，发光时附加的功能基团与腺嘌呤部分共面（几何要求），所述功能基团包括至少一个芳香环和一个具有额外电子对可轻易离域进入直接连接或内置到杂原子的扩展π系统中，并与发光腺嘌呤的电子受体酮基团建立稳定的扩展共振的电子给体原子或基团。这样的电子给体原子或基团以阴离子形式存在，特别有助于进一步向红移发射波长；或（b）直接连接到腺嘌呤核的C-2、C-4、C-5或C-7位置之一或多个位置上，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有助于进一步向红移发射波长。

  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.