4-([1,1'-biphenyl]-4-yl)-3,6-dihydro-2H-pyran | 343597-29-5

• 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: 4-([1,1'-biphenyl]-4-yl)-3,6-dihydro-2H-pyran
• 英文别名: 4-(4-phenylphenyl)-3,6-dihydro-2H-pyran
• CAS: 343597-29-5
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: VZHMCARYZHUHJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-([1,1'-biphenyl]-4-yl)-3,6-dihydro-2H-pyran 在 三氟化硼乙醚 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 3-(4-Phenylphenyl)oxolane-3-carbaldehyde
  参考文献：
  名称：

  New Synthesis of 3-Aryl-2,5-dihydrofurans

  摘要：

  We present a straightforward synthesis of 3-aryl-2,5-dihydrofurans by ring contraction of 4-aryl-3,6-dihydro-2H-pyrans with the repeated treatment of MCPBA and BF3-OEt2. The building block 3-aryltetrahydrofuran-3-carboxylic acid with potential biological activities was also prepared.

  DOI：

  10.3987/com-06-10795
• 作为产物：
  描述：

  2-BIPHENYLMAGNESIUM BROMIDE 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 4-([1,1'-biphenyl]-4-yl)-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  New Synthesis of 3-Aryl-2,5-dihydrofurans

  摘要：

  We present a straightforward synthesis of 3-aryl-2,5-dihydrofurans by ring contraction of 4-aryl-3,6-dihydro-2H-pyrans with the repeated treatment of MCPBA and BF3-OEt2. The building block 3-aryltetrahydrofuran-3-carboxylic acid with potential biological activities was also prepared.

  DOI：

  10.3987/com-06-10795

文献信息

• Reductive Carbocyclization of Homoallylic Alcohols to <i>syn</i> -Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway
  作者：Chinmoy Kumar Hazra、Jinhoon Jeong、Hyunjoong Kim、Mu-Hyun Baik、Sehoon Park、Sukbok Chang

  DOI：10.1002/anie.201713285

  日期：2018.3.1

  carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2‐disubstituted arylcyclobutanes. The reaction proceeds in a cis‐selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring‐closing pathway.

  通过使用氢硅烷作为还原剂，提供了一系列1,2-二取代的芳基环丁烷，已经开发出有机硼烷催化的均烯丙醇还原性碳环化反应。在温和条件下，反应以顺式选择方式高效进行。包括氘加扰和Hammett研究在内的机理研究以及DFT计算均提出了双闭环途径。
• POMAHOB N. A.; KANTOR E. A.; MUSAVIROV R. S.; RAXMANKULOV D. L., ZH. ORGAN. XIMII, 1979, 15, HO 5, 1059-1064
  作者：POMAHOB N. A.、 KANTOR E. A.、 MUSAVIROV R. S.、 RAXMANKULOV D. L.

  DOI：——

  日期：——
• Oxidative C H alkynylation of 3,6-dihydro-2H-pyrans
  作者：Ran Zhao、Guidong Feng、Xiaodong Xin、Honghao Guan、Jing Hua、Renzhong Wan、Wei Li、Lei Liu

  DOI：10.1016/j.cclet.2019.03.027

  日期：2019.7

  Current synthesis of alpha-substituted 3,6-dihydro-2H-pyrans dominantly relies on functional group transformation. Herein, a direct and practical oxidative C-H alkynylation and alkenylation of 3,6-dihydro-2H-pyran skeletons with a range of potassium trifluoroborates is developed. The metal-free process is well tolerated with a wide variety of 3,6-dihydro-2H-pyrans, rapidly providing a library of 2,4-disubstituted 3,6-dihydro-2H-pyrans with diverse patterns of alpha-functionalities for further diversification and bioactive small molecule identification. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• New Synthesis of 3-Aryl-2,5-dihydrofurans
  作者：Meng-Yang Chang、Chun-Yu Lin、Chun-Li Pai

  DOI：10.3987/com-06-10795

  日期：——

  We present a straightforward synthesis of 3-aryl-2,5-dihydrofurans by ring contraction of 4-aryl-3,6-dihydro-2H-pyrans with the repeated treatment of MCPBA and BF3-OEt2. The building block 3-aryltetrahydrofuran-3-carboxylic acid with potential biological activities was also prepared.