6-methyl-6-phenyl-6H-benzo[c]chromene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-methyl-6-phenyl-6H-benzo[c]chromene
• 英文别名: 6-Methyl-6-phenylbenzo[c]chromene
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: SUXNZPGLGWDERQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯并呋喃 在 盐酸 、 四甲基乙二胺 、 lithium 作用下， 以 乙醚 、 水 为溶剂， 反应 26.0h， 生成 6-methyl-6-phenyl-6H-benzo[c]chromene
  参考文献：
  名称：

  A General Synthetic Route to 6,6-Substituted-6H-dibenzo[b,d]pyrans from Dibenzofuran

  摘要：

  The reaction of dibenzofuran 1, lithium pieces (2.2 equiv), and TMEDA (2.2 equiv) in dry ether under reflux led to a solution of the corresponding C, O-dilithiated intermediate 2 which, upon treatment with different ketones or aldehydes (0.8 equiv) at -78 degrees C, afforded, after hydrolysis and dehydration, 6,6-substituted-6H-dibenzo[b,d]pyrans 3 in good yields. The reaction undergoes reductive ring opening and cyclization, and the intermediate diol 4e was isolated.

  DOI：

  10.1021/jo061415r

文献信息

• Substitution Controlled Functionalization of <i>ortho</i>-Bromobenzylic Alcohols via Palladium Catalysis: Synthesis of Chromenes and Indenols
  作者：Lodi Mahendar、Gedu Satyanarayana

  DOI：10.1021/jo402763m

  日期：2014.3.7

  transformation of simple ortho-bromobenzyl tertiary alcohols to chromenes is presented. Their formation is believed to proceed via the formation of a five-membered palladacycle, which, in turn, involves in an intermolecular homocoupling with the second ortho-bromobenzyltertiary alcohol to yield the homo-biaryl bond followed by intramolecular C–O bond formation. Interestingly, when there is an allylic substituent

  提出了一种有效的多米诺骨牌钯催化的简单的邻溴苄苄基叔醇向色烯的转化。据信它们的形成是通过形成五元的palladacycle来进行的，而该五元的palladacycle又与第二邻位分子发生了分子间的均质偶联。-溴苄基叔醇产生均联-芳基键，然后形成分子内C-O键。有趣的是，当苄基碳原子上存在一个烯丙基取代基时，观察到化学选择性开关，其优选分子内Heck偶联并得到茚基。此外，已经证实叔醇官能团对于提供偶联产物必不可少，而伯/仲苄醇的使用则通过可能的还原脱溴和随后的氧化作用提供了简单的羰基产物，这归因于β-氢的存在（ s）。
• Synthesis of 9-Substituted Fluorenols and Heteroring-fused Analogues by Intramolecular C–H Functionalization
  作者：Yuji Kurimoto、Koichi Mitsudo、Seiji Suga

  DOI：10.1246/cl.200807

  日期：2021.2.5

  A method for the selective synthesis of 9-substituted fluorenols (FOLs) was developed by suppressing intermolecular cyclization and promoting intramolecular C–H functionalization. This protocol was...

  通过抑制分子间环化和促进分子内 C-H 官能化，开发了一种选择性合成 9-取代芴醇 (FOL) 的方法。该协议是...
• Photocatalytic dehydrogenated etherification of 2-aryl benzylic alcohols
  作者：Zhihui Liang、Chao Liu、Jiajun Fan、Mingze Wang、Xuanyu Yan、Mingqiang Huang、Shunyou Cai

  DOI：10.1039/d2gc02030k

  日期：——

  we describe an efficient and practical method for the conversion of 2-aryl benzylic alcohols into the corresponding chromenes through visible-light-induced photoredox catalysis. This protocol has been applied to a wide range of benzylic alcohols, involving pharmaceuticals and natural products, with the synergistic interactions of 2-bromoanthraquinone, O2, nBu4NBr and K2CO3 in EtOH under visible-light

  在这里，我们描述了一种通过可见光诱导的光氧化还原催化将 2-芳基苯甲醇转化为相应色烯的有效且实用的方法。该协议已应用于广泛的苯甲醇，包括药物和天然产物，在可见光照射下，2-溴蒽醌、O 2、n Bu 4 NBr 和 K 2 CO 3在 EtOH 中具有协同作用。该协议在结构复杂的 6 H-苯并[ c ]色烯合成中的后期应用证明了其合成效用。
• A General Synthetic Route to 6,6-Substituted-6<i>H</i>-dibenzo[<i>b</i>,<i>d</i>]pyrans from Dibenzofuran
  作者：Bin Wang、Minxiong Li、Shansheng Xu、Haibin Song、Baiquan Wang

  DOI：10.1021/jo061415r

  日期：2006.10.1

  The reaction of dibenzofuran 1, lithium pieces (2.2 equiv), and TMEDA (2.2 equiv) in dry ether under reflux led to a solution of the corresponding C, O-dilithiated intermediate 2 which, upon treatment with different ketones or aldehydes (0.8 equiv) at -78 degrees C, afforded, after hydrolysis and dehydration, 6,6-substituted-6H-dibenzo[b,d]pyrans 3 in good yields. The reaction undergoes reductive ring opening and cyclization, and the intermediate diol 4e was isolated.