3',4'-didemethoxy-4-deoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin | 105608-71-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3',4'-didemethoxy-4-deoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin
• 英文别名: 4',5'-didemethoxy-4',5'-dioxodeoxypodophyllotoxin；5-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-3-methoxycyclohexa-3,5-diene-1,2-dione
• CAS: 105608-71-7
• 化学式: C₂₀H₁₆O₇
• 分子量: 368.343
• InChiKey: CPSSZJPWVUOTCG-PDSMFRHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3',4'-didemethoxy-4-deoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin 生成 (5R,5aR,8aR)-5-(2-azido-4,5-dihydroxy-3-methoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
  参考文献：
  名称：

  AYRES, DAVID C.;RITCHIE, TIMOTHY J., J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 9, C. 2573-2578

  摘要：

  DOI：
• 作为产物：
  描述：

  鬼臼毒素 在 palladium 10% on activated carbon 、 氢气 、 硝酸 、 溶剂黄146 、 丙酸 作用下， 95.0 ℃ 、202.66 kPa 条件下， 反应 5.07h， 生成 3',4'-didemethoxy-4-deoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin
  参考文献：
  名称：

  Synthesis and Insecticidal Activity of New Deoxypodophyllotoxin-Based Phenazine Analogues against Mythimna separata Walker

  摘要：

  In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, a series of new deoxypodophyllotoxin-based phenazine analogues modified in their E-ring were prepared, and their structures were well characterized by H-1 NMR, HRMS, ESI-MS, IR, optical rotation, and mp. The absolute steric configuration of one key isomer was unambiguously confirmed by X-ray crystallography. Their insecticidal activity was examined against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at the concentration of 1 mg/mL. All derivatives showed delayed insecticidal activity. Especially compound 9i, containing p-methoxybenzoylamnio at the C-9' position of deoxypodophyllotoxin-based phenazine fragment, exhibited the most promising insecticidal activity with the final mortality rate of 72.4%. According to the symptoms of the tested M. separata, the derivatives likely displayed an antimolting hormone effect. In addition, preliminary structure-activity relationships were observed. These suggested that the proper length of the side chain of alkylacylamino might be important for their insecticidal activity, and introduction of the acylamino groups at the C-9' position of deoxypodophyllotoxin-based phenazine fragment usually afforded more potent compounds than those containing the same ones at the C-10' position. This will pave the way for further design, structural modification, and development of deoxypodophyllotoxin-based derivatives as insecticidal agents.

  DOI：

  10.1021/jf4011033

文献信息

• Lignans and related phenols. Part 18. The synthesis of quinones from podophyllotoxin and its analogues
  作者：David C. Ayres、Timothy J. Ritchie

  DOI：10.1039/p19880002573

  日期：——

  The preparation of quinones from podophyllotoxin and peltatins of the aryltetrahydronaphthalene class by oxidative demethylation is described. The derivation of 2′-substituted ortho-quinones from these products by the reductive addition of azide, bromide, and chloride and subsequent oxidation by periodate is reported. Acid-catalysed reactions of ortho-quinones with alcohols are described including

  描述了通过鬼臼四氢萘类的鬼臼毒素和peltatins通过氧化脱甲基制备醌的方法。据报道，通过叠氮化物，溴化物和氯化物的还原性加成以及随后的高碘酸盐的氧化，从这些产物中衍生出2'-取代的邻醌。描述了邻醌与醇的酸催化反应，包括还原性甲基化的不寻常实例。