2,2'-diphenylmethanedialdehyde | 138771-00-3

• 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'-diphenylmethanedialdehyde
• 英文别名: bis(2-formylphenyl)methane；2,2'-methylenedibenzaldehyde；2-[(2-Formylphenyl)methyl]benzaldehyde
• CAS: 138771-00-3
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: SUAWTTCQEBBFMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  380.2±22.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-diphenylmethanedialdehyde 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 乙醚 为溶剂， 生成 rac-2-bromo-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene
  参考文献：
  名称：

  The First Efficient Synthesis and Optical Resolution of Monosubstituted Cyclotribenzylenes

  摘要：

  首次开发了一种新颖且高产率的合成路线，通过苯与适当单取代二醇20的环加成反应，制备单取代环三苯基烯6。该单取代二醇20源自相应二苯基烯前体19的臭氧化。二苯基烯本身可从廉价原料经过五步骤大量制备。运用此合成策略，实现了大规模制备单溴取代环三苯基烯12a。进一步通过溴锂交换后续用外部亲电试剂淬灭或铜介导的氰化反应，还合成了另外四种单取代环三苯基烯21至24。X射线分析与温度依赖性核磁共振研究表明，这些分子采取了刚性的冠形构象。翻转能垒较高，温度需远超120°C才发生翻转。此外，这类单取代环三苯基烯具有平面手性，经高效液相色谱光学拆分，我们首次获得了平面手性C1对称环三苯基烯，即光学纯的12a对映体，其圆二色谱在整个光谱范围内呈现精确的镜像关系。

  DOI：

  10.1055/s-2002-23541
• 作为产物：
  描述：

  5-二苯并环庚烯酮 在 lithium aluminium tetrahydride 、 三氯化铝 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 2,2'-diphenylmethanedialdehyde
  参考文献：
  名称：

  The First Efficient Synthesis and Optical Resolution of Monosubstituted Cyclotribenzylenes

  摘要：

  首次开发了一种新颖且高产率的合成路线，通过苯与适当单取代二醇20的环加成反应，制备单取代环三苯基烯6。该单取代二醇20源自相应二苯基烯前体19的臭氧化。二苯基烯本身可从廉价原料经过五步骤大量制备。运用此合成策略，实现了大规模制备单溴取代环三苯基烯12a。进一步通过溴锂交换后续用外部亲电试剂淬灭或铜介导的氰化反应，还合成了另外四种单取代环三苯基烯21至24。X射线分析与温度依赖性核磁共振研究表明，这些分子采取了刚性的冠形构象。翻转能垒较高，温度需远超120°C才发生翻转。此外，这类单取代环三苯基烯具有平面手性，经高效液相色谱光学拆分，我们首次获得了平面手性C1对称环三苯基烯，即光学纯的12a对映体，其圆二色谱在整个光谱范围内呈现精确的镜像关系。

  DOI：

  10.1055/s-2002-23541

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING OR PREVENTING PNEUMOVIRUS INFECTION AND ASSOCIATED DISEASES<br/>[FR] COMPOSES, COMPOSITIONS ET METHODES DE TRAITEMENT OU DE PREVENTION D'INFECTIONS PNEUMOVIRALES ET DE MALADIES ASSOCIEES
  申请人：VIROPHARMA INCORPORATED

  公开号：WO1999038508A1

  公开（公告）日：1999-08-05

  (EN) Compounds, compositions and methods are provided for the prophylaxis and treatment of infections caused by viruses of the Pneumovirinae subfamily of Paramyxoviridae and diseases associated with such infections.(FR) L'invention concerne des composés, des compositions et des méthodes de prophylaxie et de traitement d'infections causées par les virus de la famille des Paramyxoviridae, et plus précisément de la sous-famille des Pneumovirinae, et de maladies associées à ces infections.

  (中文) 提供了用于预防和治疗由Pneumovirinae亚科的Paramyxoviridae病毒引起的感染以及与此类感染相关的疾病的化合物、组合物和方法。
• Orthocyclophanes. 1. Synthesis and characterization of [14]- and [15]orthocyclophanes and bicyclic biscyclophanes
  作者：Woo Young Lee、Chang Hee Park、Young Dong Kim

  DOI：10.1021/jo00041a007

  日期：1992.7

  [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.
• Synthesis of polynuclear aromatic dialdehydes in hydrogen fluoride-antimony pentafluoride
  作者：Mutsuo Tanaka、Masahiro Fujiwara、Hisanori Ando、Yoshie Souma

  DOI：10.1021/jo00063a057

  日期：1993.5
• Fast Photochromism of the Imidazole Dimers Bridged by Group 14 Atoms
  作者：Hiroki Ito、Sho Tanaka、Katsuya Mutoh、Jiro Abe

  DOI：10.1021/acs.orglett.0c02072

  日期：2020.7.17

  We developed fast photochromic imidazole dimers bridged by group 14 atoms. These compounds reversibly break the C-N bond to generate the colored open-ring biradical form. The colored form thermally reproduces the initial colorless form in the microsecond time scales. Furthermore, the color of the biradical can be easily controlled by the introduction of two different types of the imidazolyl radicals. These results give attractive insights for the further development of fast photochromic imidazole dimers.
• Orthocyclophanes. 4. Functionalization of [1n]Orthocyclophanes on the Aromatic Rings
  作者：Woo Young Lee、Chang Hee Park、Eun Hee Kim

  DOI：10.1021/jo00095a026

  日期：1994.8

  Functionalization of the [1(n)]orthocyclophanes ([1(n)]OCPs) has been accomplished by introducing groups on the aromatic rings of the cycles. Dilithiation of dibromoaromatic 10 followed by condensation with various aromatic dialdehydes, such as 14, 20, and 30, gave rise to [1(n)]OCP cycles bearing methoxy groups on the aromatic rings. Several polymethoxy[1(n)]OCPs have been prepared that are reasonably soluble inorganic solvents, in contrast to their parent hydrocarbons. Since methoxy functions can be converted to phenolic hydroxy groups and then to other functionalities, the methoxy derivatives may have broad applications to the modification of [1(n)]OCPs for the preparation of a variety of supramolecules.