2-(2-bromophenyl)propanal | 212626-88-5

• 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-(2-bromophenyl)propanal
• CAS: 212626-88-5
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: HTKTXCAKKKTRSF-UHFFFAOYSA-N

物化性质

• 沸点：
  266.2±15.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)propanal 在 ammonium acetate 、 氨 、 magnesium oxide 、 对甲苯磺酸 、 丙二腈 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 5-(1-(2-bromophenyl)ethyl)-7-(6-morpholinopyridin-3-yl)pyrido[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Structure–activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors

  摘要：

  The synthesis and SAR of a novel series of non-nucleoside pyridopyrimidine inhibitors of the enzyme adenosine kinase (AK) are described. It was found that pyridopyrimidines with a broad range of medium and large non-polar substituents at the 5-position potently inhibited AK activity. A narrower range of analogues was capable of potently inhibiting adenosine phosphorylation in intact cells indicating an enhanced ability of these analogues to penetrate cell membranes. Potent AK inhibitors were found to effectively reduce nociception in animal models of thermal hyperalgesia and persistent pain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00602-8
• 作为产物：
  描述：

  邻溴氰苄 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 4.33h， 生成 2-(2-bromophenyl)propanal
  参考文献：
  名称：

  Synthesis of Biphenyls Mimicking the Structure of the Antimitotic Rhazinilam

  摘要：

  DOI：

  10.1021/jo980697v

文献信息

• Synthesis of rac-<mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.svg"><mml:mi>α</mml:mi></mml:math>-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst
  作者：Peng Gao、Miaolin Ke、Tong Ru、Guanfeng Liang、Fen-Er Chen

  DOI：10.1016/j.cclet.2021.07.068

  日期：2022.2

  the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic

  这项工作详细介绍了一类水溶性 PNP 配体的制备，这些配体因配体苯环上取代物的性质而异。这些配体被掺入水溶性铑-PNP络合物催化剂中，用于一系列末端芳基烯烃的区域选择性加氢甲酰化，从而以良好至极好的收率（高达 97%）和支链-区域选择性（高达 40:1 b / l比率）。此外，克级和多样化的合成转化证明了该方法在非甾体抗炎药中的合成应用。
• Primary Amine/CSA Ion Pair: A Powerful Catalytic System for the Asymmetric Enamine Catalysis
  作者：Chen Liu、Qiang Zhu、Kuo-Wei Huang、Yixin Lu

  DOI：10.1021/ol200747x

  日期：2011.5.20

  A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (−)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities

  只需将金鸡纳生物碱衍生的二胺与手性樟脑磺酸（CSA）混合，即可轻松获得新型的含有手性抗衡离子的离子对催化剂。发现9-氨基（9-脱氧）表-奎宁8和（-）-CSA的混合物是具有匹配手性的最佳催化剂，可以使α-支化醛的直接胺化以定量收率进行，并且几乎完美对映选择性。0.5mol％的催化剂负载量足以催化反应，并且已经成功地证明了克数规模的对生物重要的α-甲基苯基甘氨酸的对映选择性合成。
• HNTf₂-Catalyzed Regioselective Preparation of Polysubstituted Naphthalene Derivatives Through Alkyne–Aldehyde Coupling
  作者：Sudipta Ponra、Maxime R. Vitale、Véronique Michelet、Virginie Ratovelomanana-Vidal

  DOI：10.1021/acs.joc.5b00353

  日期：2015.3.20

  We report herein the preparation of polysubstituted naphthalene derivatives by the original Brønsted-acid-catalyzed benzannulation reaction of phenylacetaldehydes with alkynes. This reaction, which was usually performed with Lewis acids under thermal activation, is efficiently promoted by 15 mol % of triflimide (HNTf2) at room temperature under metal-free and mild reaction conditions and leads with

  我们在这里报道了通过苯乙醛与炔烃的原始布朗斯台德酸催化苯环化反应制备多取代的萘​​衍生物。通常在无金属和温和的反应条件下，室温下用15摩尔％的三氟甲酰亚胺（HNTf 2）可以有效地促进该反应，该反应通常用路易斯酸在热活化下进行。官能化萘的收率为41–78％。提出了催化循环以及该催化体系在环氧化物和乙缩醛衍生物的相关苯环化转化中的一些进一步应用。
• Asymmetric Fluorination of α-Branched Aldehydes by Chiral Primary Amine Catalysis: Reagent-Controlled Enantioselectivity Switch
  作者：Linfeng Cui、Yang’en You、Xueling Mi、Sanzhong Luo

  DOI：10.1021/acs.joc.8b00279

  日期：2018.4.6

  Asymmetric fluorination of α-branched aldehydes catalyzed by chiral primary amines under mild conditions has been developed. Both enantiomers could be obtained with good yields (up to 96%) and a high enantioselectivity (up to 90% ee) by a simple swap of the fluorination reagents.

  已经开发了在温和条件下手性伯胺催化的α-支链醛基的不对称氟化。两种对映异构体可以通过简单地交换氟化试剂而以良好的收率（高达96％）和高的对映选择性（高达90％ee）获得。
• Magnetic nanoparticle-supported ferrocenylphosphine: a reusable catalyst for hydroformylation of alkene and Mizoroki–Heck olefination
  作者：M. Nasiruzzaman Shaikh、Md. Abdul Aziz、Aasif Helal、Mohamed Bououdina、Zain H. Yamani、Tae-Jeong Kim

  DOI：10.1039/c6ra03859j

  日期：——

  nanoparticles (MNP) to yield Fe3O4@dop-BPPF. The resulting ferrocenylphosphine on magnetic nanoparticles was characterized by SEM, EDS, XRD, TEM, TGA, and VSM. The magnetic nature of the materials was investigated. Fe3O4@dop-BPPF exhibits very high catalytic activity for the Pd-catalyzed Mizoroki–Heck reaction and exceptionally high regioselectivity for the Rh-catalyzed hydroformylation reaction with branched

  我们提出多巴胺（dop）共轭双（二苯基膦基）二茂铁基乙胺（BPPFA）功能化的磁性纳米粒子（Fe 3 O 4）。甲二茂铁（ η 5 -C 5 H ^ 4 -PPh 2 } 铁η 5 -C 5 H ^ 3 -1-PPH 2 -2-CH（Me）的NH-CH 2 -CH 2 -4Ph -1,2-通过（1- [1'，2-双（二苯基膦基）-二茂铁基]乙酸乙酯）与多巴胺盐酸盐反应形成dop-BPPF制备了OH }）配体（dop-BPPF）的特征在于NMR，IR，FTIR，EA和FAB-MS。该配体被锚定在超小（6-8 nm）磁性纳米颗粒（MNP）上，产生Fe 3 O 4 @ dop-BPPF。通过SEM，EDS，XRD，TEM，TGA和VSM对磁性纳米颗粒上生成的二茂铁基膦进行了表征。研究了材料的磁性。Fe 3 O 4 @ dop-BPPF对Pd催化的Mizoroki-Heck反应具有很高的催化活