5-羟基-2,8-二甲基-6,9-二氢-4H-氧杂卓并[3,2-g]苯并吡喃-4-酮 | 14729-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 中文名称: 5-羟基-2,8-二甲基-6,9-二氢-4H-氧杂卓并[3,2-g]苯并吡喃-4-酮
• 英文名称: pteroxylin
• 英文别名: ptaeroxylin；5-hydroxy-6,9-dihydro-2,8-dimethyl-4H-oxepino[3,2-g]chromen-4-one；desoxykarenin；5-hydroxy-2,8-dimethyl-6,9-dihydropyrano[3,2-h][1]benzoxepin-4-one
• CAS: 14729-11-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: IUIHYYSAVUBPQO-UHFFFAOYSA-N

物化性质

• 熔点：
  533.535 °C
• 沸点：
  434.4±45.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)
• 碰撞截面：
  153.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-allyl-5-hydroxy-2-methyl-7-(2-methylprop-2-en-1-yl)oxy-4H-chromen-4-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以64%的产率得到5-羟基-2,8-二甲基-6,9-二氢-4H-氧杂卓并[3,2-g]苯并吡喃-4-酮
  参考文献：
  名称：

  Ptaeroxylin (Desoxykarenin) 的合成：来自 Sneezewood 树 Ptaeroxylonobliquum 的一种不寻常的色素

  摘要：

  描述了从喷嚏树中分离出的 oxepinochromone ptaeroxylin（也称为脱氧卡列宁）的首次合成，其中关键步骤是克莱森重排和闭环复分解以形成七元氧杂环。

  DOI：

  10.1055/s-2008-1078250

文献信息

• Synthesis of the Oxepinochromone Natural Products Ptaeroxylin (Desoxykarenin), Ptaeroxylinol, and Eranthin
  作者：Marjorie Bruder、Paul L. Haseler、Marina Muscarella、William Lewis、Christopher J. Moody

  DOI：10.1021/jo902117e

  日期：2010.1.15

  7-hydroxyl group, allylation of the 5-hydroxyl, followed by Claisen rearrangement under microwave conditions with concomitant deprotection of the 7-hydroxyl. Alkylation of the 7-hydroxyl with the appropriate allyl bromide provides a precursor for ring-closing metathesis to deliver the oxepinochromone ring system. Eranthin was obtained by a similar strategy involving Claisen rearrangement to transfer

  据报道，氧代庚并二氢吡喃苯丙酸的合成得到了改善，同时还合成了相关的天然产物戊苯二酚和卵黄质。通过7-羟基的选择性反应，5-羟基的烯丙基化，随后在微波条件下的克莱森重排以及7-羟基的脱保护的情况下，从色酮降冰片苷原中获得了Pereroxylin和Ptaeroxylinol。7-羟基与适当的烯丙基溴的烷基化提供了用于闭环复分解以递送氧代庚并色酮环系统的前体。通过涉及克莱森重排以将烯丙基从降钙素原的C-7羟基选择性地转移至C-8的类似策略获得了Eranthin。
• COMPOUNDS AND METHODS FOR MODULATING THE SILENCING OF A POLYNUCLEOTIDE OF INTEREST
  申请人：Jin Peng

  公开号：US20120071539A1

  公开（公告）日：2012-03-22

  Methods and compositions comprising chemical compounds that modulate the silencing of a polynucleotide of interest in a cell are provided. Such chemical compounds when used in combination with an appropriate silencing element can be used to modulate (increase or decrease) the level of the polynucleotide targeted by the silencing element. Methods of using such compositions both in therapies involving RNAi-mediated suppression of gene expression, as well as, in vitro methods that allow for the targeted modulation of expression of a polynucleotide of interest are provided. Pharmaceutical or cosmetic compositions comprising such compounds and silencing elements also are disclosed. Methods for screening a compound of interest for the ability to modulate the activity of a heterologous silencing element also are provided.