methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate | 901-36-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate
• 英文别名: 12-methoxy-7-oxo-podocarpa-8,11,13-trien-16-oic acid methyl ester；12-Methoxy-7-oxo-podocarpa-8,11,13-trien-16-saeure-methylester；1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-6-methoxy-1,4a-dimethyl-9-oxo-, methyl ester, (1S,4aS,10aR)-；methyl (1S,4aS,10aR)-6-methoxy-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate
• CAS: 901-36-0
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: MABBDZWYIBJBFO-QRQLOZEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate 在 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 cerium(III) chloride 、 三氟化硼乙醚 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙二醇 、 溶剂黄146 为溶剂， 反应 19.17h， 生成 1,1,10-trimethyl-6-methoxy-1,2,3,4-tetrahydroanthracene
  参考文献：
  名称：

  Skeletal Rearrangements of Ring C Aromatic Diterpenoids

  摘要：

  通过重排 13-甲氧基托塔拉-5,8,11,13-四烯-7α-醇 (2) 而得到的萘衍生物的结构 13-甲氧基托塔拉-5,8,11,13-四烯-7α-醇 (2) 的结构已修订为 5-(5′-异丙基-6′-甲氧基-2′-甲基-1′-萘基)-2-甲基戊-2-烯(7)。 (7).13-甲氧基托塔拉-8,11,13-三烯（4）的一个次要氧化产物被确认为 确定为 4-甲氧基-3,3-二甲基-7-(1′,3′,3′-三甲基-2′-氧代环己基)异苯并呋喃-1(3H)-酮(16)。 (16) 并通过 X 射线晶体学确认了其结构。甲基 12-甲氧基十二碳-8,11,13-三烯-19-酸甲酯（12）已转化为一种 中间体，用于合成线性二萜伞形酮 [3-(1′-羟基-1′-甲基乙基)-5,5,9-三甲基-5,6,7,8-四氢蒽-1,2-二酮] (15) 的中间体。 (15).

  DOI：

  10.1071/c97198
• 作为产物：
  描述：

  罗汉松酸 在 chromium(VI) oxide 、 乙酸酐 、 sodium hydride 、 sodium hydroxide 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 0.75h， 生成 methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate
  参考文献：
  名称：

  Phenolic Diterpenoid Derivatives as Anti-Influenza A Virus Agents

  摘要：

  A series of diterpenoid derivatives based on podocarpic acid were synthesized and evaluated as anti influenza A virus agents. Several of the novel podocarpic acid derivatives exhibited nanomolar activities against an HINI influenza A virus (A/Puerto Rico/8/34) that was resistant to two anti-influenza drugs, oseltamivir and amantadine. This class of compounds inhibits the influenza virus by targeting the viral hemagglutinin-mediated membrane fusion. These results indicated that podocarpic acid derivatives may serve as potential drug candidates to fight drug-resistant influenza A virus infections.

  DOI：

  10.1021/ml500533x

文献信息

• Coupling reactions of diterpenoid η2-tetracarbonylmanganese complexes with alkynes
  作者：Richard C. Cambie、Michael R. Metzler、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1016/0022-328x(92)83317-b

  日期：1992.5

  A number of tetracarbonylmanganese complexes derived from podocarpic acid (1) have been coupled with acetylene or diphenylacetylene to give steroidal analogues in high yield. Several modes of activating these manganese complexes towards coupling reactions were investigated, including oxidative decarbonylation at room temperature and thermal promotion.

  许多衍生自罗汉果酸（1）的四羰基锰配合物已与乙炔或二苯乙炔偶合，从而以高收率获得甾族类似物。研究了活化这些锰配合物以进行偶联反应的几种方式，包括室温下的氧化脱羰作用和热促进作用。
• Acid-Promoted Fries Rearrangements of Benzannulated Lactones
  作者：Richard C. Cambie、Lorna H. Mitchell、Peter S. Rutledge

  DOI：10.1071/c98023

  日期：——

  The scope of acid-promoted Fries rearrangements of benzannulated lactones has been examined. The reaction is applicable to seven-membered lactones possessing a sufficiently activated aromatic ring but not to six-membered lactones, and it proceeds in higher yield for diterpenoid lactones than for lower molecular weight lactones. The structures of the 2,6-methano-bridged benzoxocin side products (23), (24), and (25) from rearrangement of the diterpenoid lactone (11) have been assigned.

  研究了苯并内酯在酸促进下进行弗里斯重排的范围。 进行了研究。该反应适用于具有足够活化芳香环的七元内酯 但不适用于六元内酯。 二萜内酯的产率高于分子量较低的内酯。 二萜内酯的产率高于分子量较低的内酯。2,6-甲桥苯并氧杂环己烷副产品（23,6-甲桥苯并氧杂环己烷）的结构为 2,6-甲桥苯并氧羰基副产物(23)、(24)和(25)的结构。 二萜内酯 (11) 重排生成的 2,6-甲桥苯并恶嗪副产品 (23)、(24) 和 (25) 的结构已经确定。
• Reactions of η2-tetracarbonylmanganese complexes derived from podocarpic acid with electrophiles; functionalization of ring C
  作者：Richard C. Cambie、Michael R. Metzler、Clifton E.F. Rickard、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1016/0022-328x(92)80117-g

  日期：1992.6

  se(I) complexes derived from podocarpic acid (1) with electrophilic bromine or iodine in CCl4 leads to 14-halogenated derivatives inaccessible by direct halogenation. Similar reactions in protic solvents lead to the formation of γ-lactones in high yield. The structure of one of these was established unequivocally by X-ray crystallography. Attempted oxidation of the CMn bond with a number of reagents

  衍生自罗汉果酸（1）的四羰基锰（I）配合物与亲电溴或碘在CCl 4中的反应导致直接卤化无法获得的14卤代衍生物。在质子溶剂中的类似反应导致高产率地形成γ-内酯。通过X射线晶体学明确地确定了其中之一的结构。通常证明用多种试剂尝试氧化C bondMn键是不成功的。
• Rotatory dispersion and circular dichroism studies of some α-tetralones
  作者：R.C. Cambie、L.N. Mander、A.K. Bose、M.S. Manhas

  DOI：10.1016/s0040-4020(01)93227-2

  日期：1964.1

  The rotatory dispersion and circular dichroism spectra of several ketones conjugated with an aromatic ring (derived from diterpenoids and steroids) have been studied. These compounds show Cotton effect curves with peaks near 350mμ. Extremely weak UV absorption maxima in the 320- 350 mμ region can be detected for these ketones in iso-octane solution. This would indicate that the perturbing light wave

  研究了几种与芳香环共轭的酮的旋转分散和圆二色性光谱（衍生自二萜和类固醇）。这些化合物显示出棉花效应曲线，其峰值接近350mμ。可以在异辛烷溶液中检测到这些酮在320-350mμ区域内极弱的紫外线吸收最大值。这将表明，扰动的光波在这样的共轭酮中诱导出非常小的电偶极矩，但引起了很大的磁偶极矩。
• Organomanganese complexes of podocarpic acid derivatives
  作者：Richard C. Cambie、Michael R. Metzler、Clifton E.F. Rickard、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1016/0022-328x(92)80023-q

  日期：1992.2

  Cyclomanganation reactions of podocarpic acid derivatives containing aldehyde, ketone, ester, or oxime groups as directing functionalities have been investigated. Attempted complexation of amide-containing ligands proved generally to be unsuccessful whereas benzylic ketones gave their corresponding tetracarbonyl complexes in high yields. Complexation of ligands containing either two potential sites

  已经研究了包含醛，酮，酯或肟基团作为指导官能团的罗汉果酸衍生物的环锰化反应。尝试证明含酰胺配体的络合通常是不成功的，而苄基酮则以高收率得到了它们相应的四羰基络合物。还研究了包含两个潜在的潜在锰基位点或两个潜在的连接基团的配体的络合，并通过NMR或X射线晶体学明确地确定了分离出的络合物的结构