双[(2-羟甲基)苯基]甲烷 | 38059-08-4

• 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: 双[(2-羟甲基)苯基]甲烷
• 英文名称: bis<(2-hydroxymethyl)phenyl>methane
• 英文别名: 2,2'-bis(hydroxymethyl)diphenylmethane；2,2'-methanediyl-di-benzyl alcohol；2,2'-Methandiyl-di-benzylalkohol；2,2'-Bis-(hydroxymethyl)-diphenylmethan；[2-[[2-(Hydroxymethyl)phenyl]methyl]phenyl]methanol
• CAS: 38059-08-4
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: AVGMBLAIDTUQSB-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  404.3±35.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  双[(2-羟甲基)苯基]甲烷 在 吡啶 、 三溴化磷 、 苯 作用下， 生成 Bis<(2-bromomethyl)phenyl>methane
  参考文献：
  名称：

  Syntheses of Macrocyclic Compounds

  摘要：

  DOI：

  10.1021/ja01113a040
• 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 双[(2-羟甲基)苯基]甲烷
  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

• Construction of Sulfonyl Dibenzofused Medium‐Size Oxacycles via Bi(OTf)₃‐Catalyzed Friedel‐Crafts‐Type Annulation
  作者：Meng‐Yang Chang、Nai‐Chen Hsueh

  DOI：10.1002/adsc.202300456

  日期：2023.8.10

  with benzofused cycloethers is described. This single-step strategy provides a variety of functionalized dibenzofused medium-size (9–12) oxacycles through the formation of carbon-carbon and carbon-oxygen single bonds. Further, the oxidative application of target oxacycles was investigated. The chemical structures of the key products were determined based on the single-crystal X-ray analysis. In the overall

  本文描述了Bi(OTf) 3催化磺酰基邻羟基苯乙酮与苯并稠合环醚的弗里德尔-克来福特型成环反应。这种单步策略通过形成碳-碳和碳-氧单键提供了多种官能化二苯并稠合中等尺寸（9-12）氧杂环。此外，还研究了目标氧杂环化合物的氧化应用。通过单晶X射线分析确定了主要产物的化学结构。在整个过程中，产生了水作为副产品。
• Process for producing diarylmethanes or their derivatives
  申请人：Nippon Petrochemicals Company, Limited

  公开号：EP0890562A1

  公开（公告）日：1999-01-13

  A method to produce diarylmethane or its derivatives by condensation reaction can be carried out without difficulty and without the deterioration of catalyst, and the intended product can be produced inexpensively by recovering and recycling used alcohol. In the method, dimethoxymethane and an aromatic compound are reacted at a temperature of 80 to 400°C with an acid catalyst. Further, the method comprises the steps of (1) reacting alcohol with formaldehyde using an acid catalyst to obtain acetal; (2) reacting the acetal and an aromatic compound using an acid catalyst to obtain a reaction mixture containing diarylmethane or its derivatives and alcohol; (3) separating and recovering diarylmethane or its derivatives and alcohol from the reaction mixture, and (4) recycling at least a portion of the recovered alcohol to the step (1).

  一种通过缩合反应生产二芳基甲烷或其衍生物的方法，不仅操作简便，而且不会使催化剂变质，还可以通过回收和循环使用废酒精，以低廉的成本生产出预期产品。在该方法中，二甲氧基甲烷和芳香族化合物在 80 至 400°C 的温度下与酸催化剂发生反应。此外，该方法还包括以下步骤：(1) 使用酸催化剂使乙醇与甲醛反应，得到缩醛；(2) 使用酸催化剂使缩醛和芳香族化合物反应，得到含有二芳基甲烷或其衍生物和乙醇的反应混合物；(3) 从反应混合物中分离并回收二芳基甲烷或其衍生物和乙醇；(4) 至少将回收的部分乙醇循环用于步骤(1)。
• Yamato, Takehiko; Sakaue, Naozumi; Furusawa, Takashi, Journal of Chemical Research, Miniprint, 1991, # 9, p. 2414 - 2438
  作者：Yamato, Takehiko、Sakaue, Naozumi、Furusawa, Takashi、Tashiro, Masahi、Prakash, G.K.Surya、Olah, George A.

  DOI：——

  日期：——
• Orthocyclophanes. 2. Starands, a new family of macrocycles of spirobicyclic polyketals with a 2n-crown-n moiety
  作者：Woo Young Lee、Chang Hee Park

  DOI：10.1021/jo00077a044

  日期：1993.12

  Synthesis and functionalization of higher members of the [1n]orthocyclophanes, or [1n]OCPs, have been investigated. Oxidation of the benzylic methylenes in [1n]OCPs gave the polyoxo derivatives. Exhaustive oxidation of all methylenes in even-numbered [1n]OCPs gave rearranged isomers of the cyclopolyketal structure instead of the corresponding polyoxo derivatives. We propose the class name ''starands'' for this new family of crown compounds for their star-shaped crown ether structure. Detailed synthesis and characterization of two starands are described.
• 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.