1-(3-溴丙基)-3-甲基苯 | 103324-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3-溴丙基)-3-甲基苯
• 英文名称: 1-(3-bromopropyl)-3-methylbenzene
• CAS: 103324-39-6
• 化学式: C₁₀H₁₃Br
• mdl: MFCD09744407
• 分子量: 213.117
• InChiKey: SATMXWWRNVMPEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-溴丙基)-3-甲基苯 在 [Pd(μ-I)(Cy₂PtBu)]₂ 、 magnesium 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 1.01h， 生成 1-chloro-2-fluoro-3-(1-(m-tolyl)propyl)benzene
  参考文献：
  名称：

  空气稳定的 PdI 二聚体实现远程功能化：以前所未有的速度获得氟化 1,1-二芳基烷烃

  摘要：

  我们报告了在室温下在不到 10 分钟的反应时间内在长达 11 个碳的距离上进行的远程芳基化。空气稳定的 Pd 二聚体 [Pd(μ-I)(PCy 2 t Bu)] 2实现了前所未有的速度。

  DOI：

  10.1002/anie.202113667
• 作为产物：
  描述：

  3-(m-甲基苯基)-1-丙醇 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(3-溴丙基)-3-甲基苯
  参考文献：
  名称：

  Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity

  摘要：

  The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2] octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(-)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[ 2.2.2] octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM(3)R). Compared to 1 and 5, (R)-(-)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(-)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(-)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.

  DOI：

  10.1016/j.bmc.2019.06.016

文献信息

• Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands
  作者：Yuyang Dong、Colton J. Lund、Gerard J. Porter、Ryan M. Clarke、Shao-Liang Zheng、Thomas R. Cundari、Theodore A. Betley

  DOI：10.1021/jacs.0c09839

  日期：2021.1.20

  Investigation of 6 via single-crystal X-ray crystallography, NMR and EPR spectroscopies, and computations revealed a Ni(II)-iminyl radical formulation, similar to its dipyrrinato congener. Complex 4 exhibits enantioselective intramolecular C-H bond amination to afford N-heterocyclic products from 4-aryl-2-methyl-2-azidopentanes. Catalytic C-H amination occurs under mild conditions (5 mol % catalyst, 60 °C)

  将三苯甲基取代的双恶唑啉 (TrHBOX) 制备为先前报道的能够进行闭环胺化催化的联吡啶镍系统的手性类似物。用二价 NiI2(py)4 进行配体金属化，然后还原钾石墨，得到一价 (TrHBOX)Ni(py) (4)。将 1.4 equiv 的 1-金刚基叠氮化物的苯溶液缓慢添加到 4 中生成四叠氮基 (TrHBOX)Ni(κ2-N4Ad2) (5) 和末端亚胺基加合物 (TrHBOX)Ni(NAd) (6)。通过单晶 X 射线晶体学、NMR 和 EPR 光谱学和计算对 6 进行的研究揭示了一种 Ni(II)-亚胺基自由基配方，类似于其双吡喃酮同系物。配合物 4 表现出对映选择性分子内 CH 键胺化，可从 4-aryl-2-methyl-2-azidopentanes 得到 N-杂环产物。催化 CH 胺化在温和条件下（5 mol% 催化剂，60 °C）发生，并以适中的产率（29%-87%）提供吡咯烷产物，ee
• B(C₆F₅)₃-Catalyzed Diastereoselective Formal (4 + 1)-Cycloaddition of Vinylcyclopropanes and Et₂SiH₂
  作者：Peng-Wei Long、Martin Oestreich

  DOI：10.1021/acs.orglett.1c01565

  日期：2021.6.18

  afford 3,4-disubstituted silolanes is reported. The reaction sequence commences with the known B(C6F5)3-catalyzed alkene hydrosilylation with dihydrosilanes. Cleavage of the remaining Si–H bond in the hydrosilylation product assisted by B(C6F5)3 leads to formation of a cyclopropane-stabilized silylium ion. The activated cyclopropane ring is then opened by the in situ-generated borohydride accompanied

  据报道，乙烯基环丙烷和 Et 2 SiH 2的正式 (4 + 1)-环加成反应得到 3,4-二取代的硅酮。反应顺序从已知的B(C 6 F 5 ) 3催化的烯烃与二氢硅烷的氢化硅烷化开始。在 B(C 6 F 5 ) 3 的帮助下，氢化硅烷化产物中剩余的 Si-H 键断裂导致形成环丙烷稳定的甲硅烷离子。活化的环丙烷环随后被原位生成的硼氢化物打开，伴随着对硅酮的闭环。非对映选择性通过机械模型合理化。
• Synthesis of Sultams and Cyclic <i>N</i>-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C–H Amidation
  作者：Dayou Zhong、Di Wu、Yan Zhang、Zhiwu Lu、Muhammad Usman、Wei Liu、Xiuqiang Lu、Wen-Bo Liu

  DOI：10.1021/acs.orglett.9b01732

  日期：2019.8.2

  unique role in drug discovery and synthetic chemistry. A direct synthesis of sultams by an intramolecular C(sp3)–H amidation reaction using an iron complex in situ derived from Fe(ClO4)2 and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation

  环磺酰胺（sultams）在药物发现和合成化学中起着独特的作用。据报道，使用Fe（ClO 4）2和氨基吡啶配体原位生成铁配合物，通过分子内C（sp 3）-H酰胺化反应可直接合成阿马丹。如22个实例所示，该策略的特点是易于获得的催化剂，并能耐受多种底物（产率高达89％）。还实现了用于合成环状N-磺酰基酮亚胺的一锅铁催化的酰胺化/氧化方法，产率高达92％（八个实例）。该方法的合成效用通过克级反应和将产物衍生为环稠合的杜仲而得到证实。
• Direct<i>meta</i>‐C−H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine‐Based Template
  作者：Massimo Brochetta、Tania Borsari、Sukdev Bag、Sadhan Jana、Siddhartha Maiti、Alessio Porta、Daniel B. Werz、Giuseppe Zanoni、Debabrata Maiti

  DOI：10.1002/chem.201902811

  日期：2019.8.6

  The development of efficient and mild methods for the synthesis of organofluorine compounds is of foremost interest in various fields of chemistry. A direct pyrimidine‐based selective meta‐C−H perfluoroalkenylation of arenes involving several commercially available perfluoroolefins is described. The synthetic versatility of the protocol is demonstrated by an extensive substrate scope including different

  在各种化学领域中，最重要的兴趣是开发有效且温和的合成有机氟化合物的方法。描述了一种基于嘧啶的直接基于嘧啶的选择性间-C H全氟烯基化反应，涉及几种可商购的全氟烯烃。通过广泛的底物范围（包括不同的苄基磺酰基，烷基亚芳基和苯基乙酸支架）证明了该方案的合成多功能性。该方法包括的一般性元布洛芬的-C-H perfluoroalkenylation，所述引导组和革兰氏规模的反应的容易裂解被呈现。
• Reductive activation of arenes
  作者：T. A. Vaganova、E. V. Panteleeva、P. S. Yuferov、Yu. V. Rebitva、V. D. Shteingarts

  DOI：10.1007/s11172-006-0366-0

  日期：2006.6

  Reductive alkylation of benzonitrile, ortho-, meta-, para-tolunitriles, and 1-naphthonitrile by sequential action of alkali metal and alkyl bromide in liquid ammonia results in corresponding alkylarenes and 1-alkyl-1-cyanocyclohexa-2,5-dienes. The experimental conditions for target synthesis of the specified products are found. A method of synthesis of 1-(ω-bromoalkyl)-1-cyanocyclohexa-2,5-dienes based

  通过碱金属和烷基溴在液氨中的连续作用，苄腈、邻-、间-、对-甲苯腈和 1-萘甲腈的还原烷基化产生相应的烷基芳烃和 1-烷基-1-氰基环六-2,5-二烯。找到了目标合成指定产物的实验条件。基于芳香腈与 α,ω-二溴烷烃 Br(CH2)nBr (n = 3) 的双电子还原产物的相互作用合成 1-(ω-溴代烷基)-1-氰基环己-2,5-二烯的方法−5) 开发。