2,7-bis(bromomethyl)-9,10-dihydrophenanthrene | 43012-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,7-bis(bromomethyl)-9,10-dihydrophenanthrene
• 英文别名: 2,7-Bis(brommethyl)-9,10-dihydrophenanthren
• CAS: 43012-24-4
• 化学式: C₁₆H₁₄Br₂
• 分子量: 366.095
• InChiKey: LQZSOSIZRTZDJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  447.1±35.0 °C(Predicted)
• 密度：
  1.626±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,7-bis(bromomethyl)-9,10-dihydrophenanthrene 在 18-冠醚-6 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 4-[(E)-2-[7-[(E)-2-[7-[(E)-2-[7-[(E)-2-[4-(dioctylamino)phenyl]ethenyl]-9,10-dihydrophenanthren-2-yl]ethenyl]-9,10-dihydrophenanthren-2-yl]ethenyl]-9,10-dihydrophenanthren-2-yl]ethenyl]-N,N-dioctylaniline
  参考文献：
  名称：

  Nanoscale Push-Push Dihydrophenanthrene Derivatives as Novel Fluorophores for Two-Photon-Excited Fluorescence

  摘要：

  Outperforming fluorescein by far, elongated fluorophores (e.g. 1) give rise to large two-photon absorption cross-sections σ2 in the visible-red or NIR region and high quantum fluorescence yields Φ (see figure; GM = 10-50 cm4 s photon-1 ). This opens interesting prospects in the field of two-photon microscopy imaging of cell membranes.

  DOI：

  10.1002/1521-3773(20010601)40:11<2098::aid-anie2098>3.0.co;2-0
• 作为产物：
  描述：

  聚合甲醛 、 9,10-二氢菲 在 磷酸 、 氢溴酸 、 溶剂黄146 作用下， 反应 28.0h， 以55%的产率得到2,7-bis(bromomethyl)-9,10-dihydrophenanthrene
  参考文献：
  名称：

  具有聚苯撑基的双卟啉供体-受体化合物中的电子转移显示出弱的距离依赖性

  摘要：

  已经合成了一系列亚苯基桥连的双卟啉加合物，包含一个、两个或三个苯桥。提供了完整的合成细节。为了研究光化学电子转移，加入了混合金属，锌在一个卟啉大环中，而 Fe III（双咪唑）在另一个大环中。当光激发时，一个电子从 Zn 转移到 Fe III

  DOI：

  10.1021/ja00041a047

文献信息

• The Synthesis of Some Head to Head Linked DNA Minor Groove Binders
  作者：Abedawn I. Khalaf、Andrew R. Pitt、Martin Scobie、Colin J. Suckling、John Urwin、Roger D. Waigh、Robert V. Fishleigh、Steven C. Young、William A. Wylie

  DOI：10.1016/s0040-4020(00)00432-4

  日期：2000.7

  A series of head to head linked dimers of heterocyclic amino acids has been prepared for investigation of affinity and selectivity in binding to the minor groove of DNA. The selection of targets for synthesis was led by computer based design. Several novel dicarboxylic acid linkers including indoles, phenanthrenes, a fluorenone, and a bisbenzothiophene have been included. Analysis of binding to DNA

  已经制备了一系列首尾相连的杂环氨基酸二聚体，用于研究与DNA小沟结合的亲和力和选择性。合成目标的选择由基于计算机的设计主导。已经包括几种新颖的二羧酸连接基，包括吲哚，菲，芴酮和双苯并噻吩。通过印迹分析与DNA的结合表明对衍生自2,7-二氢菲二羧酸的化合物具有很高的亲和力，并且对包含至少4个AT对的AT富集区域具有主要选择性，但具有跨越两个CG碱基对的能力。
• New quadrupolar fluorophores with high two-photon excited fluorescence
  作者：Lionel Ventelon、Mireille Blanchard-Desce、Laurent Moreaux、Jerome Mertz

  DOI：10.1039/a906182g

  日期：——

  New quadrupolar fluorophores that exhibit enhanced two-photon excited fluorescence were designed according to a molecular engineering approach based on push-push and pull-pull elongated molecules built from a rigid conjugated core (either dihydrophenanthrene or dithienothiophene).

  新型四极荧光团具有增强的双光子激发荧光，是根据一种分子工程方法设计的，该方法基于由刚性共轭核心（二氢菲或二噻吩）构建的推拉拉伸分子。
• An infinite catenane self-assembled by π⋯π interactions
  作者：Leigh Loots、Leonard J. Barbour

  DOI：10.1039/c2cc37953h

  日期：——

  Phenanthrenyl-based metallocycles are mechanically interlinked to form an infinite catenated chain. The formation of the catenane is governed by an infinite π⋯π stack involving the phenanthrenyl moieties.

  菲基金属环以机械方式相互连接，形成一条无限的卡烯烃链。该链烷的形成受菲基分子的无限Ïâ¯Ï堆栈的控制。
• Cross-Linked Peptides and Proteins, Methods of Making Same, and Uses Thereof
  申请人：Lin Qing

  公开号：US20140057857A1

  公开（公告）日：2014-02-27

  Cross-linked proteins and peptides, and methods of making and uses of such cross-linked proteins and peptides. The cross-linked proteins and peptides have rigid, distance-matching bismethylene aryl cross-linking moieties. Compositions comprising the cross-linked proteins and peptides can be used as pharmaceutical delivery formulations. The cross-linked proteins and peptides can have improved properties, such as cell permeability, as compared to the parent protein or peptide.

  跨链蛋白和肽以及制备和使用这种跨链蛋白和肽的方法。跨链蛋白和肽具有刚性、距离匹配的双亚甲基芳基交联基团。包含跨链蛋白和肽的组合物可用作药物递送配方。与母体蛋白或肽相比，跨链蛋白和肽可以具有改善的特性，例如细胞渗透性。
• Synthesis of cell-permeable stapled BH3 peptide-based Mcl-1 inhibitors containing simple aryl and vinylaryl cross-linkers
  作者：Avinash Muppidi、Kenichiro Doi、Carlo P. Ramil、Hong-Gang Wang、Qing Lin

  DOI：10.1016/j.tet.2014.05.104

  日期：2014.10

  We report the synthesis of a series of distance-matching aryl and vinylaryl cross-linkers for constructing stapled peptides containing cysteines at i,i+7 positions. Langevin dynamics simulation studies helped to classify these cross-linkers into two categories: the rigid cross-linkers with narrower S S distance distribution and the flexible cross-linkers with wider S S distance distribution. The stapled Noxa BH3 peptides with the flexible distance-matching cross-linkers gave the highest degree of helicity as well as the most potent inhibitory activity against Mcl-1. However, the stapled peptides with the highest hydrophobicity showed the most efficient cellular uptake. Together, this work illustrates the divergent nature of binding affinity and cellular uptake, and the vital importance of choosing appropriate cross-linkers in constructing stapled peptides with the drug-like properties. (C) 2014 Elsevier Ltd. All rights reserved.