2-(3-phenyl-propa-1,2-dienyl)biphenyl | 916588-75-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(3-phenyl-propa-1,2-dienyl)biphenyl
• CAS: 916588-75-5
• 化学式: C₂₁H₁₆
• 分子量: 268.358
• InChiKey: ISOYRKXPIDFPRV-UHFFFAOYSA-N

物化性质

• 沸点：
  486.6±25.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(3-phenyl-propa-1,2-dienyl)biphenyl 以 N-甲基吡咯烷酮 为溶剂， 反应 5.0h， 以80%的产率得到9-benzyl-phenanthrene
  参考文献：
  名称：

  Site-Specific Preparation of 2-Carboalkoxy-4-substituted Naphthalenes and 9-Alkylphenanthrenes and Evidence for an Allene Intermediate in the Novel Base-Catalyzed Cyclization of 2-Alkynylbiphenyls

  摘要：

  [GRAPHICS]A site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes is described. The successful cyclization of an allene intermediate provides supportive evidence for the previously proposed mechanism.

  DOI：

  10.1021/ol0620850
• 作为产物：
  描述：

  2-碘联苯 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 四丁基溴化铵 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 2-(3-phenyl-propa-1,2-dienyl)biphenyl
  参考文献：
  名称：

  Site-Specific Preparation of 2-Carboalkoxy-4-substituted Naphthalenes and 9-Alkylphenanthrenes and Evidence for an Allene Intermediate in the Novel Base-Catalyzed Cyclization of 2-Alkynylbiphenyls

  摘要：

  [GRAPHICS]A site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes is described. The successful cyclization of an allene intermediate provides supportive evidence for the previously proposed mechanism.

  DOI：

  10.1021/ol0620850

文献信息

• Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of <i>N</i>-Tosylhydrazones with Terminal Alkynes
  作者：Mohammad Lokman Hossain、Fei Ye、Zhenxing Liu、Ying Xia、Yi Shi、Lei Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo501489c

  日期：2014.9.19

  for the synthesis of phenanthrenes through the copper-catalyzed reaction of aromatic tosylhydrazones with terminal alkynes is explored. The reaction proceeds via the formation of an allene intermediate and subsequent six-π-electron cyclization–isomerization, affording phenanthrene derivatives in good yields. The transformation can be performed in two ways: (1) with N-tosylhydrazones derived from [1,1

  探索了通过芳族甲苯磺酰hydr与末端炔烃的铜催化反应合成菲的新方法。该反应通过形成烯丙基中间体和随后的六-π电子环化-异构化而进行，从而以高收率获得了菲衍生物。转化可以通过两种方式进行：（1）用ñ -tosylhydrazones从[1,1'-联苯] -2- carbaldehydes和末端炔烃的原料和（2）与衍生ñ -tosylhydrazones从芳香醛和衍生以2-炔基联苯为原料。这种新的菲合成使用容易获得的原料和廉价的铜催化剂，并且具有广泛的官能团相容性。
• Copper(I)‐Catalyzed Reactions of 2’‐Cyano‐biaryl‐2‐aldehyde <i>N</i>‐Tosylhydrazones with Terminal Alkynes: An Approach towards 9‐Amino‐10‐alkynylphenanthrene Modules
  作者：Jiaying Lv、Ruimao Hua

  DOI：10.1002/adsc.202300682

  日期：2023.10.13

  Herein, we report a cascade strategy towards 9-amino-10-alkynylphenanthrenes, which involves copper(I)-catalyzed reactions of 2’-cyano-biaryl-2-aldehyde N-tosylhydrazones and terminal alkynes in a one-pot manner. In addition, the obtained 9-amino-10-alkynylphenanthrenes could be engaged as π-extending building blocks in the synthesis of 9H- dibenzo[3,4:5,6]borinino[1,2-b]phenanthro-[9,10-e][1,2]azaborinine

  在此，我们报告了一种针对 9-氨基-10-炔基菲的级联策略，其中涉及铜（I）催化的 2'-氰基-联芳基-2-醛 N-甲苯磺酰腙和末端炔烃的一锅反应。此外，所获得的9-氨基-10-炔基菲可以作为π-延伸结构单元参与9 H-二苯并[3,4:5,6]borinino[1,2- b ]phenanthro-[9的合成,10- e ][1,2]氮杂硼啉(BNTBA)是一种新型BN嵌入PACs，与其全碳类似物三苯并[f,k,m]四吩( TBA )相比显示出不同的性能。本合成方法从易于获得的商业底物开始，为合成高功能化菲和π延伸BN嵌入PAC提供了一种实用的方法。
• Site-Specific Preparation of 2-Carboalkoxy-4-substituted Naphthalenes and 9-Alkylphenanthrenes and Evidence for an Allene Intermediate in the Novel Base-Catalyzed Cyclization of 2-Alkynylbiphenyls
  作者：Yi Wang、Donald J. Burton

  DOI：10.1021/ol0620850

  日期：2006.11.9

  [GRAPHICS]A site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes is described. The successful cyclization of an allene intermediate provides supportive evidence for the previously proposed mechanism.