5-Chloro-16-ethenyl-9,17-dioxa-13-thiatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6,11,14-hexaen-2-one | 1314110-60-5

• 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: 5-Chloro-16-ethenyl-9,17-dioxa-13-thiatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6,11,14-hexaen-2-one
• CAS: 1314110-60-5
• 化学式: C₁₆H₉ClO₃S
• 分子量: 316.765
• InChiKey: MOQHPPDXKVQHKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-羟基-5-氯苯乙酮 在 四丁基碘化铵 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 反应 12.33h， 生成 5-Chloro-16-ethenyl-9,17-dioxa-13-thiatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6,11,14-hexaen-2-one 、 5-Chloro-16-ethenyl-9,17-dioxa-14-thiatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6,11(15),12-hexaen-2-one 、 (15S,16R)-5-chloro-16-ethenyl-9,17-dioxa-13-thiatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6,11-pentaen-2-one
  参考文献：
  名称：

  Photo-reorganization of 3-alkoxy-6-chloro-2-(thiophen-3-yl)-4H-chromen-4-ones: Regioselective cyclization via γ-hydrogen abstraction

  摘要：

  Regioselective photocyclization of 3-alkoxy-6-chloro-4H-chromen-4-ones bearing thiophen-3-yl moiety at 2-position has been described. These chromenones on irradiation by the pyrex filtered UV-light produced a diverse array of novel angular tetracyclic photoproducts. Of these, mostly the cyclic dihydro and dehydrogenated photoproducts had the gem-dihydro functionality and exocyclic double bonds onto the fused pyran ring respectively, which is unprecedent in these chromenones. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.04.002

文献信息

• Regioselective Photocyclization Reactions of 3-Allyloxy-6-chloro-2-(thiophen-3-yl)-4<i>H</i>-chromen-4-one: Solvent Effect
  作者：Ramesh C. Kamboj、Dinesh Kumar、Rita Arora、Surinder Berar、Geeta Sharma

  DOI：10.1002/jhet.1006

  日期：2013.2

  photo-irradiation of thienylchromenone resulted in the regioselective cyclization which is exclusively controlled by the nature of solvent used as reaction medium. Compared to nonpolar medium, polar solvent furnished a diverse array of novel angular tetracyclic photoproducts with gem-dihydro functionality and exocyclic double bonds on the fused pyran ring, which is unprecedented to best of our knowledge

  噻吩基色酮的光辐照导致区域选择性 环化，其仅由用作反应介质的溶剂的性质来控制。与非极性介质相比，极性溶剂提供了各种各样的新颖角四环光产物，它们在稠合的吡喃环上具有gem-dihydro功能和环外双键，据我们所知，这是前所未有的。