1,2-双(2-溴苯基)-2-羟基乙酮 | 61592-98-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-双(2-溴苯基)-2-羟基乙酮
• 英文名称: 1,2-bis(2-bromophenyl)-2-hydroxyethan-1-one
• 英文别名: 2,2’-dibromobenzoin；1,2-bis(2-bromophenyl)-2-hydroxyethanone
• CAS: 61592-98-1
• 化学式: C₁₄H₁₀Br₂O₂
• 分子量: 370.04
• InChiKey: OXKYIPSJQMUPSW-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  464.8±40.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1,2-双(2-溴苯基)-2-羟基乙酮 在 potassium bromate 、 磷化氢 、 sodium hydroxide 、 Celite 、 氢碘酸 、 碘 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 bis(2-bromophenyl)methane
  参考文献：
  名称：

  Orthocyclophanes. 1. Synthesis and characterization of [14]- and [15]orthocyclophanes and bicyclic biscyclophanes

  摘要：

  [1(4)]- and [1(5)]orthocyclophanes have been designed, synthesized and characterized. Dimetalation of bis(2-bromophenyl)methane (14) to the corresponding dilithio reagent 21, followed by reaction with aromatic dialdehydes bis(2-formylphenyl)methane (20) and 1,2-bis(2-formylbenzyl)benzene (27), gave cyclic diols 22 and 28, respectively. Oxidation of the diols with PCC to the corresponding cyclic diketones 23 and 29, followed by palladium-catalyzed reduction, afforded [1(4)]- and [1(5)]orthocyclophanes, 4 and 5. Bicyclic biscyclophanes were also prepared from the cyclic diketones giving rise to a new family of cyclophanes. Treatment of 23 and 29, respectively, with McMurry or Clemmensen reagents gave rise to intramolecular olefination to provide bicyclic biscyclophanes 24 and 30. Pd-catalyzed hydrogenation of 24 and 30 also gave 4 and 5. The benzylic positions of the cycloheptatriene moieties in 24 and 30 were very susceptible to oxidation to give ketones 26 and 32.

  DOI：

  10.1021/jo00041a007
• 作为产物：
  描述：

  邻溴苯甲醛 在 rubidium carbonate 、 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 1,6-二苯基-4-羟基己烷-3-酮 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 以16%的产率得到1,2-双(2-溴苯基)-2-羟基乙酮
  参考文献：
  名称：

  与三唑鎓衍生的碳催化剂的高度化学选择性直接交叉的脂族芳香环肽缩合反应。

  摘要：

  首次显示，三唑鎓预催化剂促进（在碱存在下）脂族和邻位取代的芳族醛之间的高度化学选择性的交叉酰化缩合反应。一个ø -溴原子可以作为一个临时定向基团，以确保高的化学选择性（无论在芳环上的其它取代基的性质），其然后可被方便地除去。该方法的范围很广并且操作简单，因为它不需要任何偶合伙伴的预活化来确保选择性。初步数据表明，使用手性预催化剂，该反应的高对映选择性变体是可行的。

  DOI：

  10.1021/jo101791w

文献信息

• (±)Methanodibenzodiazocine tethered [C-H]δ+ functional site: Study towards benzoin condensation and Baylis-Hillman reactions
  作者：ARRURI SATHYANARAYANA、GANESAN PRABUSANKAR

  DOI：10.1007/s12039-015-0837-7

  日期：2015.5

  New heterocyclic ring systems consisting of (±) methanodibenzodiazocine and imidazolium/ benzimidazolium salts were synthesized in very good yield. Subsequently, these halide salts were subjected to the anion exchange reaction with KPF6 to yield the corresponding azolium salts in excellent yield. The possible applications of these newly prepared salts were investigated in homogeneous catalysis. Remarkable changes in the catalytic activity were observed by varying the bulkiness of N-substituent at imidazole. Catalytic activity of these newly prepared salts was tested for the benzoin condensation reaction. Exclusive formation of benzoin products were observed in good yield. Similarly, the dimerization of cyclohexen-1-one to Baylis-Hillman type product, 2-(3-oxocyclohexyl)-2-cyclohexen-1-one was studied.

  新合成的杂环环系由(±)甲烷二苯并二氮杂烯及咪唑盐/苯咪唑盐组成，得率非常好。随后，这些卤盐与KPF6进行阴离子交换反应，生成相应的杂环阳离子盐，得率极佳。研究了这些新制备盐类在均相催化中的潜在应用。通过改变咪唑中N取代基的体积，观察到催化活性发生显著变化。这些新制备盐的催化活性被测试于苯偶弧反应中，观察到苯偶弧产物的专一性形成且得率良好。同样，研究了环己烯-1-酮二聚化反应，生成Baylis-Hillman类型的产物2-(3-氧基环己基)-2-环己烯-1-酮。
• Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst
  作者：Ming Yu Jin、Sun Min Kim、Hui Mao、Do Hyun Ryu、Choong Eui Song、Jung Woon Yang

  DOI：10.1039/c3ob42486c

  日期：——

  We found that chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio. Moreover, we observed the persistent catalytic activity of the homogeneous NHC catalyst in a solution due to NHC catalyst robustness.

  我们发现，通过调节芳族醛/脂族醛比率来控制交叉的酰胆素产物的化学选择性。此外，由于NHC催化剂的坚固性，我们观察到了溶液中均相NHC催化剂的持久催化活性。
• Palladium-Catalyzed Double Carbonylative Cyclization of Benzoins: Synthesis and Photoluminescence of Bis-Ester-Bridged Stilbenes
  作者：Yosuke Tani、Takuji Ogawa

  DOI：10.1021/acs.orglett.8b03169

  日期：2018.12.7

  bis-ester-bridged stilbenes just in two steps from aldehydes. Thus, the obtained fully fused tetracyclic π-systems have a pyrano[3,2-b]pyran-2,6-dione (PPD) core on their center, showing two reversible reductions at low potentials. In addition, their photoluminescence properties are strikingly affected by the aromatic rings fused to the PPD core; bis-thieno-fused PPDs are found to be excellent fluorophores

  已开发出钯催化的安息香双羰基双环化反应，该反应仅需两个步骤即可实现醛类双酯桥联的对苯二酚的合成。因此，获得的完全稠合的四环π系统在其中心具有吡喃并[3,2 - b ]吡喃-2,6-二酮（PPD）核，在低电势下显示出两个可逆的还原。另外，它们的光致发光特性受到与PPD核稠合的芳香环的显着影响。发现双噻吩并稠合的PPD是优异的荧光团，量子产率高达0.98。
• Room-temperature phosphorescence-to-phosphorescence mechanochromism of a metal-free organic 1,2-diketone
  作者：Yosuke Tani、Morihisa Terasaki、Mao Komura、Takuji Ogawa

  DOI：10.1039/c9tc04176a

  日期：——

  An organic 1,2-diketone with intramolecular chalcogen bonding overcomes the room-temperature phosphorescence (RTP) quenching problem on amorphization, representing the first RTP-to-RTP mechanochromism of a metal-free organic molecule.

  一种含有分子内硫族元素键合的有机1,2-二酮克服了非晶化时室温磷光猝灭问题，代表了无金属有机分子的第一种磷光-磷光机械致色现象。
• Pronounced Hypsochromic Shift of Absorption Band and Improved Solubility of Bis(1,2-diaryl-1,2-ethylenedithiolato)nickels. Prospective Near-IR Dyes for Optical Data Storage
  作者：Hisayoshi Shiozaki、Hiroyuki Nakazumi、Yasuko Nakado、Teijiro Kitao

  DOI：10.1246/cl.1987.2393

  日期：1987.12.5

  atoms at the 2-position in the benzene rings of bis(1,2-diaryl-1,2-ethylenedithiolato)nickel caused a pronounced hypsochromic shift of the absorption band in near-infrared region and improved the solubility to benzene. The nickel complexes with 2-halogen atoms are effective quenchers of singlet oxygen.

  在双(1,2-二芳基-1,2-亚乙基二硫醇合)镍的苯环2-位引入卤素原子，导致近红外区吸收带发生明显的低色移，提高了对苯的溶解度. 具有 2-卤素原子的镍配合物是单线态氧的有效猝灭剂。