2'-bromo-3,5-dimethoxybiphenyl | 890854-86-1

• 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'-bromo-3,5-dimethoxybiphenyl
• 英文别名: 2-Bromo-3',5'-dimethoxybiphenyl；1-(2-bromophenyl)-3,5-dimethoxybenzene
• CAS: 890854-86-1
• 化学式: C₁₄H₁₃BrO₂
• 分子量: 293.16
• InChiKey: IWLDSTZLVWVFJN-UHFFFAOYSA-N

物化性质

• 沸点：
  363.7±27.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-bromo-3,5-dimethoxybiphenyl 在 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 [1,1';2',1'']Terphenyl-3,5,4''-triol
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 2'-bromo-3,5-dimethoxybiphenyl
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o

文献信息

• Scholl Reaction of Perylene‐Based Polyphenylene Precursors under Different Conditions: Formation of Hexagon or Octagon?
  作者：Ya Zou、Yi Han、Shaofei Wu、Xudong Hou、Chi Hao Eugene Chow、Jishan Wu

  DOI：10.1002/anie.202105427

  日期：2021.8.2

  crystallographic analysis also revealed that there is no close π–π stacking between neighboring π-conjugated skeletons. DFT calculations suggest a radical cation mechanism in the presence of FeCl3 while an arenium ion pathway for the DDQ/MeSO3H mediated Scholl reaction, which can well explain the selective formation of hexagons and octagons under different conditions. The obtained compounds showed tunable

  通过 FeCl 3介导的 Scholl 反应从基于环戊基稠合苝 (CP) 的聚苯前体 ( 1 )合成平面二苯并-过六苯衍生物 ( 2 )。然而，当 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 和甲磺酸 (MeSO 3 H) 被加入时，以几乎定量的产率获得了一个意想不到的含有八角形的负弯曲分子 ( 3 )。用过的。当包含一个 ( 4 ) 或两个 CP 单元 ( 5) 进行了测试。X 射线晶体学分析还表明，相邻的 π 共轭骨架之间没有紧密的 π-π 堆积。DFT 计算表明在 FeCl 3存在下存在自由基阳离子机制，而 DDQ/MeSO 3 H 介导的 Scholl 反应的砷离子途径可以很好地解释六边形和八边形在不同条件下的选择性形成。所得化合物显示出可调的光学和电化学性质。
• PHOSPHINE LIGANDS FOR CATALYTIC REACTIONS
  申请人：Shekhar Shashank

  公开号：US20120022252A1

  公开（公告）日：2012-01-26

  The disclosure is directed to: (a) phosphacycle ligands; (b) methods of using such phosphacycle ligands in bond forming reactions; and (c) methods of preparing phosphacycle ligands.

  本公开涉及：(a)磷环配体；(b)使用此类磷环配体进行键合反应的方法；以及(c)制备磷环配体的方法。
• Phosphine ligands for catalytic reactions
  申请人：Shekhar Shashank

  公开号：US08975443B2

  公开（公告）日：2015-03-10

  The disclosure is directed to: (a) phosphacycle ligands; (b) catalyst compositions comprising phosphacycle ligands; and (c) methods of using such phosphacycle ligands and catalyst compositions in bond forming reactions.

  本公开涉及：(a)磷环配体；(b)包含磷环配体的催化剂组合物；以及(c)使用这些磷环配体和催化剂组合物在化学键形成反应中的方法。
• Heptagon/Octagon‐Fused Diporphyrins or Spiro‐Pentagon‐Bridged Dichlorin from <i>p</i> ‐Terphenylene‐Bridged Diporphyrin
  作者：Peng Lin、Shugang Xiong、Yutao Rao、Ling Xu、Mingbo Zhou、Bangshao Yin、Atsuhiro Osuka、Jianxin Song

  DOI：10.1002/asia.202300018

  日期：2023.3.14

  AbstractIntramolecular fusion reactions of a p‐terphenylene‐bridged NiII porphyrin dimer gave different products, depending upon reaction conditions. Oxidation with Fe(OTf)3 provided syn‐ and anti‐doubly heptagon‐fused NiII porphyrin dimers showing enlarged π‐electronic networks, probably via a radical mechanism, while treatment with methanesulfonic acid provided a spiro‐pentagon‐bridged NiII chlorin dimer via acid‐catalyzed Friedel‐Crafts type cyclization. Further, a doubly octagon‐fused NiII porphyrin dimer was synthesized via a sequence of double meso‐formylation, reduction to corresponding diol, and BF3‐catalyzed cyclization.
• US8841487B2
  申请人：——

  公开号：US8841487B2

  公开（公告）日：2014-09-23