12-acetoxypodocarpic acid methyl ester | 24035-58-3

• 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: 12-acetoxypodocarpic acid methyl ester
• 英文别名: methyl 12-O-acetyl-podocarpate；12-acetoxy-podocarpa-8,11,13-trien-16-oic acid methyl ester；12-Acetoxy-podocarpa-8,11,13-trien-16-saeure-methylester；Podocarpsaeuremethylesteracetat；methyl (1S,4aS,10aR)-6-acetyloxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 24035-58-3
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: ZABWQWWKTVPXTP-RLLQIKCJSA-N

物化性质

• 熔点：
  122-123.5 °C(Solv: methanol, 50% (67-56-1))
• 沸点：
  418.1±45.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  12-acetoxypodocarpic acid methyl ester 在 chromium(VI) oxide 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 Methyl-5,6-dehydro-7-oxopodocarpat
  参考文献：
  名称：

  DERIVATIVES OF DEHYDROABIETIC AND PODOCARPIC ACIDS

  摘要：

  本文介绍了芳香树脂酸系列中腈的锂铝氢化还原成醛亚胺的过程，以及产物转化为其他衍生物的方法。注意到腈的立体化学对还原速率的影响。指出了脱氢松香烷转化为脱氢产物的过程。讨论了白杉酸的脱羧-5,6-脱氢-7-酮衍生物及其光学对映体的合成。报道了白杉酸的5,6-脱氢衍生物的氢化立体化学。说明了7-酮基团对芳香树脂酸甲酯水解速率的影响。描绘了甲基白杉酸的6-溴-7-酮衍生物与碱反应的反应过程。

  DOI：

  10.1139/v63-284
• 作为产物：
  描述：

  罗汉松酸 在 吡啶 作用下， 生成 12-acetoxypodocarpic acid methyl ester
  参考文献：
  名称：

  罗汉松科化学-III：一种新的木脂素，癸二异西里香脂醇和罗汉松心材的其他成分

  摘要：

  从罗汉松的心材中分离出一种新的木脂素，提出了新的木酚素，其名称为癸二-异西里香脂醇。已经显示该结构为2：3-双（4'-羟基-3'-甲氧基苄基）-丁丹-1：4-二醇（II，R = H），并且通过从（-）-的绝对合成来证实。苦参醇（I，R = H）。对心材提取物的进一步检查导致除先前报道的化合物马蒂固醇，α-榄香烯苷，槲皮素之外，还分离了次要成分（+）-紫杉醇，（+）-芳香金属菊酯，山奈酚和角豆蔻醇。 ，金雀异黄素和popopicatin。

  DOI：

  10.1016/s0040-4020(01)93195-3

文献信息

• Photoinduced direct 4-pyridination of C(sp3)–H Bonds
  作者：Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1039/c3sc51080h

  日期：——

  Direct substitution of hydrogen in C(sp3)–H bonds by 4-pyridine was achieved by employing benzophenone and 4-cyanopyridine in aqueous acetonitrile under photo-irradiating conditions. This simple and mild 4-pyridination proceeds in a highly chemoselective manner especially at benzylic C(sp3)–H bonds without affecting polar functional groups, and enables intermolecular formation of sterically hindered bonds between alkylaromatics and 4-pyridine. The present methodology thus serves as a powerful tool for construction of biologically active and functional molecules with 4-pyridine substructures.

  通过在光照射条件下，在含水的乙腈中使用二苯甲酮和4-氰基吡啶，实现了直接将氢原子替代到C(sp3)‒H键中形成4-吡啶基的反应。这种简单温和的4-吡啶化过程以高度化学选择性的方式进行，特别适用于苯甲位C(sp3)‒H键，且不影响极性官能团，并能够实现烷基芳香化合物与4-吡啶之间的分子间形成立体障碍的键。因此，本方法成为构建含有4-吡啶基结构的生物活性分子和功能分子的有力工具。
• Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives
  作者：Yong-Mei Cui、Eriko Yasutomi、Yuko Otani、Katsutoshi Ido、Takashi Yoshinaga、Kohei Sawada、Tomohiko Ohwada

  DOI：10.1016/j.bmc.2010.09.072

  日期：2010.12

  ether derivatives at the benzylic position of unsubstituted, dichloro, trichloro, and monobromo derivatives of the aromatic C-ring of dehydroabietic acid and podocarpic acid were synthesized and evaluated as BK channel openers in an assay system of CHO-K1 cells expressing hBKα channels. Detailed SAR analysis showed that the oximation was particularly effective in the cases of dehydroabietic acid derivatives

  合成了脱氢松香酸和罗汉果酸的芳香C环的未取代，二氯，三氯和一溴衍生物的苄基位置上的肟醚衍生物，并在表达hBKα通道的CHO-K1细胞分析系统中将其作为BK通道开放剂进行评估。详细的SAR分析表明，在脱氢松香酸衍生物的情况下，肟化作用特别有效，并且这些肟衍生物中的一些表现出比标准化合物NS1619更有效的BK通道活性。本研究为开发有效的BK通道开放剂提供了新的结构基础。
• Radical Amination of C(sp³)–H Bonds Using <i>N</i>-Hydroxyphthalimide and Dialkyl Azodicarboxylate
  作者：Yuuki Amaoka、Shin Kamijo、Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1021/jo301840e

  日期：2012.11.16

  A direct conversion of C(sp(3))-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.
• Phenolic Diterpenoid Derivatives as Anti-Influenza A Virus Agents
  作者：Zhao Dang、Katherine Jung、Lei Zhu、Hua Xie、Kuo-Hsiung Lee、Chin-Ho Chen、Li Huang

  DOI：10.1021/ml500533x

  日期：2015.3.12

  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.
• Partial Degradation and Reconstitution of Podocarpic Acid. A Novel Method of Hydrolysis of Highly Sterically Hindered Esters¹
  作者：Ernest Wenkert、B. G. Jackson

  DOI：10.1021/ja01534a055

  日期：1958.1