2'-hydroxy-6",6"-dimethylpyrano<2",3":4',5'>chalcone | 143885-71-6

• 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'-hydroxy-6",6"-dimethylpyrano<2",3":4',5'>chalcone
• 英文别名: 6-Cinnamoyl-7-hydroxy-2,2-dimethylchromen；isolonchocarpin；(E)-1-(7-hydroxy-2,2-dimethylchromen-6-yl)-3-phenylprop-2-en-1-one
• CAS: 143885-71-6
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: KVXNRZVPNCKCNO-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-6",6"-dimethylpyrano<2",3":4',5'>chalcone 在 吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 6",6"-dimethylpyrano<2",3":7,6>flavanone
  参考文献：
  名称：

  Parmar, V. S.; Vardhan, Anand; Sharma, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 1, p. 17 - 26

  摘要：

  DOI：
• 作为产物：
  描述：

  泽兰色原烯 、 苯甲醛 在 barium dihydroxide 作用下， 生成 2'-hydroxy-6",6"-dimethylpyrano<2",3":4',5'>chalcone
  参考文献：
  名称：

  13C nuclear magnetic resonance studies on pyrano- and dihydropyrano-1,3- diphenylprop-2-enones

  摘要：

  记录了 19 种不同取代的吡喃-和二氢吡喃-1,3-二苯基丙-2-烯酮的 13C NMR 谱，并对结果进行了讨论。这些数据将有助于鉴定新的天然查耳酮。

  DOI：

  10.1002/mrc.1260300619

文献信息

• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Selenium-Based Solid-Phase Synthesis of Benzopyrans I: Applications to Combinatorial Synthesis of Natural Products
  作者：K. C. Nicolaou、Jeffrey A. Pfefferkorn、Guo-Qiang Cao

  DOI：10.1002/(sici)1521-3773(20000218)39:4<734::aid-anie734>3.0.co;2-i

  日期：2000.2.18
• New fragmentation pathways in the electron impact mass spectrometry of derivatized pyrano-1,3-diphenylprop-2-enones
  作者：Virinder S. Parmar、Sunil K. Sharma、Anand Vardhan、Rakesh K. Sharma、Jørgen Møller、Per M. Boll

  DOI：10.1002/oms.1210280106

  日期：1993.1

  AbstractThe fragmentation patterns of closely related chalcones, cinnamoylchromans and cinnamoylchromenes, are reported to be strikingly different. The mass spectra of the first group show peaks typical of the fragmentation of simple chalcones balanced by additional fragmentation routes competing effectively with the typical chalcone fragmentation. For the other group with the introduced double bond the fragmentation is considerably changed. Initial loss of a methyl group gives rise to formation of the base peak in three of four examples. The [M – CH3]+ ion decomposes further, eliminating a styrene yielding the m/z 187 ion. This process may be rationalized as a retro‐Diels–Alder fragmentation of a flavanone formed on intramolecular rearrangement of the molecular ion.