1-tigloyl-3-acetyl-11-methoxyazadirachtin | 113589-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1-tigloyl-3-acetyl-11-methoxyazadirachtin
• 英文别名: 1-tigloyl-3-acetyl-11-methoxyazadirachtinin；1-O-tigloyl-3-acetyl-11-O-methylazadirachtinin；3-acetyl-11-methoxy-1-tigloylazadirachtinin；dimethyl (1S,4S,5R,6S,7R,8S,10S,14S,15S,16R,18S,19R,22S,23R,25S,26R)-23-acetyloxy-7,14-dihydroxy-4-methoxy-6,16-dimethyl-25-[(E)-2-methylbut-2-enoyl]oxy-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.18,15.01,5.06,18.07,16.010,14.022,26]heptacos-12-ene-4,22-dicarboxylate
• CAS: 113589-91-6
• 化学式: C₃₆H₄₆O₁₆
• 分子量: 734.752
• InChiKey: IRLZLBSKSFBHPL-JNIVOBJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  201
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-7-hydroxy-6-[(1S,2S,4S,6R,8S,9R,11S)-2-hydroxy-4-methoxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodecan-9-yl]-4-methoxy-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate 在 4 A molecular sieve 、 苯硒酚 、 吡啶 、 双氧水 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 3.08h， 以85%的产率得到1-tigloyl-3-acetyl-11-methoxyazadirachtin
  参考文献：
  名称：

  Synthesis of Natural Products from the Indian Neem Tree Azadirachta indica

  摘要：

  The synthesis of five natural products (3, 6, 7, 10, and 14), isolated from the Indian neem tree Azadirachta indica, is reported from a common intermediate (2). The judicious choice of transacetalization conditions allows efficient access to both the azadirachtinin (9 and 10) and the azadirachtin (3, 6, 7, and 14) skeletons.

  DOI：

  10.1021/ol7027898

文献信息

• Synthesis of Natural Products from the Indian Neem Tree <i>Azadirachta indica</i>
  作者：Gemma E. Veitch、Andrea Pinto、Alistair Boyer、Edith Beckmann、James C. Anderson、Steven V. Ley

  DOI：10.1021/ol7027898

  日期：2008.2.1

  The synthesis of five natural products (3, 6, 7, 10, and 14), isolated from the Indian neem tree Azadirachta indica, is reported from a common intermediate (2). The judicious choice of transacetalization conditions allows efficient access to both the azadirachtinin (9 and 10) and the azadirachtin (3, 6, 7, and 14) skeletons.