(2,6-dibromobenzyl)(triphenyl)phosphonium bromide

• 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: (2,6-dibromobenzyl)(triphenyl)phosphonium bromide
• 英文别名: (2,6-Dibromobenzyl)(triphenyl)phosphonium bromide；(2,6-dibromophenyl)methyl-triphenylphosphanium;bromide
• 化学式: Br*C₂₅H₂₀Br₂P
• 分子量: 591.12
• InChiKey: LMVKFAJQTHHCTK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,6-dibromobenzyl)(triphenyl)phosphonium bromide 在 tin(ll) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 9.25h， 生成 4-(2,6-dibromophenyl)-9-methoxy-4,5,6,10c-tetrahydro-3aH-pyrrolo[3,4-c]carbazole-1,3-dione
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591
• 作为产物：
  描述：

  1,3-二溴-2-(溴甲基)苯 、 三苯基膦 以 苯 为溶剂， 反应 5.0h， 以5.1 g的产率得到(2,6-dibromobenzyl)(triphenyl)phosphonium bromide
  参考文献：
  名称：

  Hyperbranched poly(phenylenevinylene) bearing pendant phenoxys for a high-spin alignment

  摘要：

  在钯催化剂的作用下，2,6-二溴-4-(3′,5′-二叔丁基-4′-乙酰氧基苯基)苯乙烯在一锅反应中聚合，随后水解和氧化得到超支化的聚[(4-(3′、5′-二叔丁基-4′-基氧基苯基）-1,2,(6)-亚苯基乙烯）]，它在三个方向上同时满足交替但非 Kekulé 型的π-共轭和悬垂苯氧基未配对电子的铁磁连接。原子力显微镜图像、异常低的溶液粘度和苯酚基团的低化学反应活性表明，这种聚合物具有高度支化的球状结构。尽管支化极为密集，但聚合物骨架中的π-共轭结构仍得以保持，这一点已在光电子学和 EPR 光谱中得到证实。即使每个单体单元的自旋浓度仅为 0.4，苯氧基聚合物的平均 S 值也达到了 3。

  DOI：

  10.1039/b203891a

文献信息

• Hyperbranched poly(phenylenevinylene) bearing pendant phenoxys for a high-spin alignment
  作者：Hiroyuki Nishide、Mitsutaka Nambo、Makoto Miyasaka

  DOI：10.1039/b203891a

  日期：2002.11.29

  2,6-Dibromo-4-(3′,5′-di-tert-butyl-4′-acetoxyphenyl)styrene was polymerized in a one-pot reaction using a palladium catalyst, and subsequent hydrolysis and oxidation yielded the hyperbranched poly[(4-(3′,5′-di-tert-butyl-4′-ylooxyphenyl)-1,2,(6)-phenylenevinylene)], which three-directionally satisfies both an alternant but non-Kekulé-type π-conjugation and the ferromagnetic connectivity of the unpaired electrons of the pendant phenoxyl. The AFM image, unusually low solution viscosity, and low chemical reactivity of the phenol group indicated the polymer to have a highly branched and globular structure. In spite of the extremely crowded branching, π-conjugation in the polymer skeleton was maintained, as indicated by photoelectron and EPR spectroscopies. The phenoxyl polymer even with a spin concentration of only 0.4 spin per monomer unit displayed an average S value of 3.

  在钯催化剂的作用下，2,6-二溴-4-(3′,5′-二叔丁基-4′-乙酰氧基苯基)苯乙烯在一锅反应中聚合，随后水解和氧化得到超支化的聚[(4-(3′、5′-二叔丁基-4′-基氧基苯基）-1,2,(6)-亚苯基乙烯）]，它在三个方向上同时满足交替但非 Kekulé 型的π-共轭和悬垂苯氧基未配对电子的铁磁连接。原子力显微镜图像、异常低的溶液粘度和苯酚基团的低化学反应活性表明，这种聚合物具有高度支化的球状结构。尽管支化极为密集，但聚合物骨架中的π-共轭结构仍得以保持，这一点已在光电子学和 EPR 光谱中得到证实。即使每个单体单元的自旋浓度仅为 0.4，苯氧基聚合物的平均 S 值也达到了 3。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20180315942A1

  公开（公告）日：2018-11-01

  The present invention relates to compounds containing fused dibenzo more-than-six-membered heterocycles or azaheterocycles. These compounds may be useful as host materials for phosphorescent electroluminescent devices.

  本发明涉及含有融合的二苯并多于六元杂环或氮杂环的化合物。这些化合物可能有用作为磷光电致发光器件的宿主材料。
• [EN] INHIBITORS OF CHECKPOINT KINASES (WEE1 AND CHK1)<br/>[FR] INHIBITEURS DE CHECKPOINT KINASES (WEE1 ET CHK1)
  申请人：WARNER LAMBERT CO

  公开号：WO2003091255A1

  公开（公告）日：2003-11-06

  This invention relates to pyrrolocarbazole derivatives according formula (I) wherein R1, R2, r7, R8 R9, X and Y are as defined in the specification wherein said derivatives specifically inhibit one or both of the checkpoint kinases Wee1 and Chk1.

  本发明涉及公式（I）中的吡咯并咔唑衍生物，其中R1，R2，r7，R8，R9，X和Y如规范中所定义，其中所述衍生物特异性地抑制检查点激酶Wee1和Chk1中的一个或两个。
• Inhibitors of checkpoint kinases (Wee1 and Chk1)
  申请人：Pfizer Inc

  公开号：US07094798B1

  公开（公告）日：2006-08-22

  This invention relates to pyrrolocarbazole derivatives according formula I wherein R1, R2, R7, R8, R9, X and Y are as defined in the specification wherein said derivatives specifically inhibit one or both of the checkpoint kinases Wee1 and Chk1

  本发明涉及公式I中的吡咯烷并咔唑衍生物，其中R1、R2、R7、R8、R9、X和Y如规范中所定义，其中这些衍生物特异性抑制检查点激酶Wee1和Chk1中的一个或两个。
• INHIBITORS OF CHECKPOINT KINASES (WEE1 AND CHK1)
  申请人：WARNER-LAMBERT COMPANY LLC

  公开号：EP1501831A1

  公开（公告）日：2005-02-02