dl-Phyllostin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dl-Phyllostin
• 英文别名: (1S,6R)-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
• 化学式: C₇H₆O₄
• 分子量: 154.122
• InChiKey: PLELZLHJHUZIGY-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dl-Phyllostin 在 三乙酰氧基硼氢化钠 作用下， 以 甲醇 为溶剂， 生成 (+/-)-parasitenone
  参考文献：
  名称：

  Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

  摘要：

  Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappa B (NF-kappa B) inhibitor that inhibits DNA binding of NF-kappa B components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-kappa B indicated that the epoxycyclohexenone moiety is the most essential element for the NF-kappa B inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.120
• 作为产物：
  描述：

  在 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 生成 dl-Phyllostin
  参考文献：
  名称：

  Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

  摘要：

  Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappa B (NF-kappa B) inhibitor that inhibits DNA binding of NF-kappa B components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-kappa B indicated that the epoxycyclohexenone moiety is the most essential element for the NF-kappa B inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.120

文献信息

• Synthesis of (.+-.)-epoxydon and related natural compounds.
  作者：Akitami ICHIHARA、Ryoji KIMURA、Kengo ODA、Koichi MORIYASU、Sadao SAKAMURA

  DOI：10.1271/bbb1961.46.1879

  日期：——

  Synthesis of (±)-phyllostine, (±)-epoxydon, (±)-epiepoxydon, (±)-epoformin and (±)-epiepoformin by the retro-Diels-Alder reaction was described.

  描述了通过逆-Diels-Alder 反应合成(±)-phyllostine、(±)-epoxydon、(±)-epiepoxydon、(±)-epoformin 和 (±)-epiepoformin的过程。
• Filling Some Blanks in a Divergent Approach to Gabosines: Enantioselective Synthesis of (–)‐Epiepoxydon, (+)‐Phyllostine, (–)‐Gabosine D, and (–)‐Gabosine E
  作者：Miguel Ángel Fresneda、Ramon Alibés、Pau Bayón、Marta Figueredo

  DOI：10.1002/ejoc.201600492

  日期：2016.7

  polyoxygenated cyclohexane target molecules. Key steps in the synthesis of (–)-gabosines D and E from (4R,6S)-3 are the stereoselective hydroxymethylation at the α-carbonyl position leading to (+)-4, and the subsequent reagent-controlled epoxidation of the carbon–carbon double bond. A branching in the sequence also allowed the synthesis of the anhydrogabosines (–)-epiepoxydon and (+)-phyllostine.

  gabosines D 和 E 的左旋对映异构体是通过不同的方法合成的，该方法同样适用于从天然来源中分离出来的右旋对映异构体的合成。该方法依赖于对甲氧基苯酚的初始去对称化，然后进行酶拆分，分别提供合成子 3 的两种对映异构体。这种多功能合成子可以进一步转化为多种多氧化环己烷目标分子。从 (4R,6S)-3 合成 (-)-gabosine D 和 E 的关键步骤是在导致 (+)-4 的 α-羰基位置的立体选择性羟甲基化，以及随后的试剂控制的碳环氧化-碳双键。
• Efficient Asymmetric Synthesis of Chiral Monomer of Epoxyquinols and (-)-Phyllostine
  作者：Hee-Il Chae、Geum-Sook Hwang、Ming-Yu Jin、Do-Hyun Ryu

  DOI：10.5012/bkcs.2010.31.04.1047

  日期：2010.4.20
• Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB
  作者：Tsuyoshi Saitoh、Eriko Suzuki、Arisa Takasugi、Rika Obata、Yuichi Ishikawa、Kazuo Umezawa、Shigeru Nishiyama

  DOI：10.1016/j.bmcl.2009.07.120

  日期：2009.9

  Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappa B (NF-kappa B) inhibitor that inhibits DNA binding of NF-kappa B components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-kappa B indicated that the epoxycyclohexenone moiety is the most essential element for the NF-kappa B inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity. (C) 2009 Elsevier Ltd. All rights reserved.