homoisoflavan | 99217-74-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: homoisoflavan
• 英文别名: 3-benzylchromane；3-benzylchroman；3-benzyl-3,4-dihydro-2H-chromene
• CAS: 99217-74-0
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: FAZPXZSNQNWJAW-UHFFFAOYSA-N

物化性质

• 沸点：
  349.9±12.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  高氯酸 、 homoisoflavan 、 乙酸酐 生成 2,4-bis-(3-benzyl-chroman-6-yl)-6-methyl-pyrylium; perchlorate
  参考文献：
  名称：

  Pfeiffer et al., Justus Liebigs Annalen der Chemie, 1949, vol. 564, p. 208,219

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苄基-2H-色烯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 homoisoflavan
  参考文献：
  名称：

  A new route to 3,4-dihydro-2H-1-benzopyrans substituted at 3-position via palladium-catalysed reactions

  摘要：

  3,4-Dihydro-2H-1-benzopyrans substituted at 3-position were prepared via palladium-catalysed reactions between a triflate and several coupling reagents (alkyl or aryl tin reagents and borane derivatives) according to Stille or Suzuki methodologies. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01209-4

文献信息

• N‐Atom Deletion in Nitrogen Heterocycles
  作者：Haitao Qin、Wangshui Cai、Shuang Wang、Ting Guo、Guigen Li、Hongjian Lu

  DOI：10.1002/anie.202107356

  日期：2021.9.13

  Examples are provided of deletion of nitrogen from natural products, synthesis of chiral O-heterocycles from commercially available chiral β-amino alcohols, formal inert C−H functionalization through a sequence of N-directed C−H functionalization and N-atom deletion reactions in which the N-atom can serve as a traceless directing group.

  切除仲胺中的氮并将两个残留片段偶联起来是一种骨架编辑策略，可用于构建具有新骨架的分子，但在很大程度上尚未被探索。在这里，我们报告了一种从 N-杂环中切除 N-原子的通用方法。该过程使用容易获得的 N-杂环作为底物，并通过 N-磺酰叠氮作用进行，然后氨磺酰叠氮化物中间体的重排，提供各种环状产物。提供了从天然产物中删除氮、从市售手性 β-氨基醇合成手性 O-杂环、通过一系列 N 导向的 CH 官能化和 N 原子缺失反应的形式惰性 CH 官能化的例子其中 N 原子可以作为一个无痕导向群。
• Synthesis and biological activity of (±)-7,3′,4′-trihydroxyhomoisoflavan and its analogs
  作者：Toshiro Noshita、Kentaro Fujita、Takeru Koga、Hidekazu Ouchi、Akihiro Tai

  DOI：10.1016/j.bmcl.2020.127674

  日期：2021.1

  Acetylcholinesterase (AChE) inhibitors and neurite outgrowth promoters are thought to alleviate the symptoms of degenerative brain disorders, such as Alzheimer's disease. We designed and synthesized a series of homoisoflavonoids based on the structure of natural homoisoflavan isolated from Dracaena cambodiana dragon’s blood. The homoisoflavonoids were then evaluated as AChE inhibitors and neurite outgrowth

  乙酰胆碱酯酶（AChE）抑制剂和神经突增生促进剂被认为可减轻变性性脑部疾病的症状，例如阿尔茨海默氏病。基于从龙血树龙血中分离得到的天然异黄酮的结构，我们设计并合成了一系列异黄酮。然后将同型异黄酮评估为AChE抑制剂和神经突增生促进剂。高异黄烷B环的儿茶酚结构对于AChE抑制很重要，并且一些高异黄酮能显着促进神经生长因子（NGF）诱导的神经突生长。
• Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives
  作者：Cinzia Conti、Nicoletta Desideri

  DOI：10.1016/j.bmc.2009.03.051

  日期：2009.5

  A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC(50)s from 0.11 to 6.62 mu M). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 mu M, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene) chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids. (C) 2009 Elsevier Ltd. All rights reserved.
• EDIBLE COMPOSITION
  申请人：Unilever PLC

  公开号：EP3344070B1

  公开（公告）日：2019-12-18