Spiro[cycloheptane-1,6a(2)-[6H]dibenzo[b,d]pyran] | 72417-26-6

• 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: Spiro[cycloheptane-1,6a(2)-[6H]dibenzo[b,d]pyran]
• 英文别名: spiro[benzo[c]chromene-6,1'-cycloheptane]
• CAS: 72417-26-6
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: CGWUKBSHMLRNCW-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  428.9±15.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 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 Spiro[cycloheptane-1,6a(2)-[6H]dibenzo[b,d]pyran]
  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

• 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.