1,3-bis(bromomethyl)-5-iodobenzene | 107164-93-2

• 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: 1,3-bis(bromomethyl)-5-iodobenzene
• 英文别名: 3,5-bis(bromomethyl)iodobenzene
• CAS: 107164-93-2
• 化学式: C₈H₇Br₂I
• 分子量: 389.856
• InChiKey: GMAQAYJAXIDDAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  1,3-bis(bromomethyl)-5-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 间二甲苯 为溶剂， 反应 4.0h， 生成 3,5-bis(diphenylphosphinoylmethyl)trimethylsilylethynylbenzene
  参考文献：
  名称：

  Synthesis and Catalytic Properties of Di- and Trinuclear Palladium Complexes with PCP-Pincer Ligands

  摘要：

  Linear and branched conjugated pincer ligands having Ph(2)p groups were synthesized: 3,3'5,5- tetrakis(diphenylphosphinomethyl)diphenylacetylene, 3,3',5,5'-tetrakis(diphenylphosphinomethyl)diphenyldiacetylene, 1,3,5-tris[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene, and hexakis[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene. Palladation of these ligands by heating with Pd(BF4)(2)(MeCN)(4) in boiling acetonitrile gave the corresponding di- and trinuclear ionic pincer palladium complexes. No individual complex was obtained from hexakis [3,5 -bis(diphenylphosphinomethyl)phenylethynyl] benzene. The ionic complexes were converted into the corresponding chloride complexes by treatment with sodium chloride in a mixture of water with methylene chloride. The structure of the ionic palladium complex with 3,3%5,5 -tetrakis(diphenylphosphinomethyl)diphenylacetylene was established by X-ray analysis. The obtained palladium complexes exhibited a considerable catalytic activity in the Heck reaction of iodobenzene with ethyl acrylate and in the Michael addition of ethyl cyanoacetate with methyl vinyl ketone. The catalytic activity per palladium atom decreases as the number of palladium atoms in the complex increases.

  DOI：

  10.1023/b:rujo.0000010214.72250.5a
• 作为产物：
  描述：

  (5-iodo-1,3-phenylene)dimethanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以35%的产率得到1,3-bis(bromomethyl)-5-iodobenzene
  参考文献：
  名称：

  Systematic Variation of Pyrrolobenzodiazepine (PBD)-Dimer Payload Physicochemical Properties Impacts Efficacy and Tolerability of the Corresponding Antibody–Drug Conjugates

  摘要：

  Cytotoxic pyrrolobenzodiazepine (PBD)-dimer molecules are frequently utilized as payloads for antibody-drug conjugates (ADCs), and many examples are currently in clinical development. In order to further explore this ADC payload class, the physicochemical properties of various PBD-dimer molecules were modified by the systematic introduction of acidic and basic moieties into their chemical structures. The impact of these changes on DNA binding, cell membrane permeability, and in vitro antiproliferation potency was, respectively, determined using a DNA alkylation assay, PAMPA assessments, and cell-based cytotoxicity measurements conducted with a variety of cancer lines. The modified PBD-dimer compounds were subsequently incorporated into CD22-targeting ADCs, and these entities were profiled in a variety of in vitro and in vivo experiments. The introduction of a strongly basic moiety into the PBD-dimer scaffold afforded a conjugate with dramatically worsened mouse tolerability properties relative to ADCs derived from related payloads, which lacked the basic group.

  DOI：

  10.1021/acs.jmedchem.0c00691

文献信息

• Desymmetrisation of Biphenyl-Based Carbohydrate Receptors: A Nonbonding Pillar in One Corner of the Cage
  作者：Anthony Davis、Lee Challinor、Emmanuel Klein

  DOI：10.1055/s-2008-1078020

  日期：2008.8

  We report a new addition to the family of biphenyl-based carbohydrate receptors, derived by replacing one out of four iso­phthalamide (diamide) linkages with the corresponding diester. The alteration results in lower binding constants, perhaps reflecting the entropic penalty for lowering receptor symmetry. However, the synthesis allows access to many related host molecules, with potential for restoring and raising affinities and tuning selectivities.

  我们报道了一种基于联苯的碳水化合物受体家族的新成员，该受体通过将其中一个异酞酰胺（二酰胺）连接替换为相应的二酯而衍生出来。这种改变导致了较低的结合常数，这可能是由于降低受体对称性所带来的熵惩罚。然而，这种合成方法让我们得以接触到许多相关的主分子，有潜力恢复和提高亲和力并调整选择性。
• A Synthetic Galectin Mimic
  作者：Brian J. J. Timmer、Arjaan Kooijman、Xander Schaapkens、Tiddo J. Mooibroek

  DOI：10.1002/anie.202104924

  日期：2021.7.12

  currently available. We now report on the design and synthesis of the first galectin mimic (6), and show that it has a higher than 65-fold preference for n-octyl-β-galactoside (8) over n-octyl-β-glucoside (7) in CD2Cl2 containing 5 % [D6]DMSO (with Ka≥4500 M−1 for 6:8). Molecular modeling informed by nOe studies reveal a high degree of interaction complementarity between 6 and galactoside 8, which is

  半乳糖凝集素是碳水化合物结合蛋白（凝集素）的半乳糖苷特异性亚类，参与各种细胞活动、某些癌症、感染、炎症和许多其他生物过程。半乳糖凝集素选择性的分子基础有据可查，并且围绕适当的相互作用互补性：用于 C−H⋅⋅⋅π 相互作用的芳香族残基和与半乳糖苷的轴向羟基形成（电荷辅助）氢键的极性残基。然而，目前还没有可用的合成模拟物。我们现在报告第一个半乳糖凝集素模拟物 ( 6 ) 的设计和合成，并表明它对正辛基-β-半乳糖苷 ( 8 ) 的偏好比正辛基-β-葡萄糖苷 ( 7 ) 高 65 倍）在含有5%[D 6 ]DMSO的CD 2 Cl 2中（对于6 : 8 ，Ka≥4500 M -1）。nOe 研究提供的分子模型揭示了6和半乳糖苷8之间高度的相互作用互补性，这与天然半乳糖凝集素中发现的相互作用互补性非常相似。
• Synthesis of hybrid dendritic molecules with diazaphospholidine oxide grafted at the surface of octavinylsilsesquioxane (OVS)
  作者：Ge Cheng、Alexandra M. Z. Slawin、Nicolas R. Vautravers、Pascal André、Russell E. Morris、Ifor D. W. Samuel、David Cole-Hamilton

  DOI：10.1039/c0ob00297f

  日期：——

  phosphine oxide ligand, which was derivatised with a series of functional groups including bromide, vinyl, allyl and terminal alkyne. Several methods to attach the resulting precursors onto octavinylsilsesquioxane (OVS), ranging from hydrosilylation, Suzuki, Heck, Grubbs or Sonogashira coupling reactions, have been investigated. Cross-metathesis of SEMI-ESPHOS oxide dendrons containing vinyl end groups

  使用单齿SEMI-ESPHOS制备了一系列树突状分子 氧化膦 配体，它被一系列官能团衍生化，包括 溴化物，乙烯基，烯丙基和末端炔基。几种方法将生成的前体附着到八乙烯基倍半硅氧烷（OVS）涉及氢化硅烷化，Suzuki，Heck，Grubbs或Sonogashira偶联反应。的交叉复分解半环氧乙烷 含有乙烯基端基的OVS催化的树枝状分子; 格拉布斯 事实证明，这种催化剂可有效地形成基于OVS的树枝状分子的前体。
• Synthesis and coordination properties of palladium(II) and platinum(II) complexes with phosphonated triphenylphosphine derivatives
  作者：Zbyněk Rohlík、Petr Holzhauser、Jan Kotek、Jakub Rudovský、Ivan Němec、Petr Hermann、Ivan Lukeš

  DOI：10.1016/j.jorganchem.2006.01.024

  日期：2006.5

  formula [MCl2L2] and one dinuclear complex trans-[Pd2Cl4(3a)2] were synthesized and their isomerization behaviour in solution was studied. The complexes were characterized by 1H, 13C, 31P and 195Pt NMR spectroscopy, mass spectrometry and far-IR spectroscopy. The X-ray structures of all complexes with 3a or 3b have usual slightly distorted square-planar geometry on the metal ion. Salts of phosphonic acids

  两种三苯基膦衍生物，[4-（二苯基膦基）苄基]膦酸二乙酯（3a）和[5-（二苯基膦基）-1,3-亚苯基]二亚甲基}双（膦酸酯）（3b），以及相应的游离酸4a和4b准备好了。这些配体通过1 H，13 C和31 P NMR光谱学和质谱法表征。全套[MCl 2 L 2 ]的Pd（II）和Pt（II）配合物和一个双核配合物反式-[Pd 2 Cl 4（3a）2合成，研究了它们在溶液中的异构化行为。通过1 H，13 C，31 P和195 Pt NMR光谱，质谱和远红外光谱对复合物进行表征。具有3a或3b的所有配合物的X射线结构在金属离子上通常具有略微扭曲的方平面几何形状。膦酸4a和4b的盐及其络合物可自由溶于水溶液；因此，它们可能在水相或双相催化中有用。
• Synthesis and Properties of Carborane-Appended <i>C</i>₃-Symmetrical Extended π Systems
  作者：Barada Prasanna Dash、Rashmirekha Satapathy、Elizabeth R. Gaillard、John A. Maguire、Narayan S. Hosmane

  DOI：10.1021/ja101845m

  日期：2010.5.12

  followed by silicon tetrachloride mediated trimerization reactions. Carborane-containing extended trimers were found to emit blue light. Incorporation of o-carborane clusters into extended pi-conjugated systems led to 22-70% enhancement of their relative fluorescence quantum yields. Decapitation of o-carborane clusters made these extended trimers water soluble, and their aqueous solutions were also found

  通过采用钯催化的 Suzuki 偶联反应和钯催化的乙酰化反应，以及四氯化硅介导的三聚反应，合成了一系列包含三到六个邻碳硼烷簇的 C(3)-对称 pi 共轭化合物。发现含有碳硼烷的延伸三聚体发出蓝光。将邻碳硼烷簇并入扩展的 pi 共轭系统导致其相对荧光量子产率提高 22-70%。邻碳硼烷簇的斩首使这些扩展的三聚体可溶于水，并且还发现它们的水溶液具有荧光，但荧光强度降低。发现附加碳硼烷的 pi 共轭化合物具有极强的热稳定性，