iriomoteolide-3a | 1009815-99-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: iriomoteolide-3a
• 英文别名: Iriomoteolide 3a；(1S,3S,7S,9E,11S,12S,13E,15S)-11,12-dihydroxy-3-[(1S,3R,4E,7E)-1-hydroxy-3-methylnona-4,7-dienyl]-7-methyl-4,16-dioxabicyclo[13.1.0]hexadeca-9,13-dien-5-one
• CAS: 1009815-99-9
• 化学式: C₂₅H₃₈O₆
• 分子量: 434.573
• InChiKey: LQBFGORJMLJPKT-RXPUTBOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  iriomoteolide-3a 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以0.12 mg的产率得到[(1S,3S,7S,9E,11S,12S,13E,15S)-7-methyl-3-[(1S,3R,4E,7E)-3-methyl-1-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxynona-4,7-dienyl]-5-oxo-12-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy-4,16-dioxabicyclo[13.1.0]hexadeca-9,13-dien-11-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Iriomoteolide-3a, a Cytotoxic 15-Membered Macrolide from a Marine Dinoflagellate Amphidinium Species

  摘要：

  A 15-membered macrolide, iriomoteolide-3a (1), with an allyl epoxide has been isolated from a marine benthic dinoflagellate Amphidinium sp. (strain HYA024), and the structure was assigned by detailed analyses of 2D NMR data. Relative and absolute configurations were elucidated on the basis of conformational studies of 1 and its acetonide (2) and modified Mosher's method of 1, respectively. Iriomoteolide3a (1) and the acetonide (2) exhibited potently cytotoxic activity against antitumor cells.

  DOI：

  10.1021/jo702440s

文献信息

• Iriomoteolide-3a, a Cytotoxic 15-Membered Macrolide from a Marine Dinoflagellate <i>Amphidinium</i> Species
  作者：Keiko Oguchi、Masashi Tsuda、Rie Iwamoto、Yumiko Okamoto、Jun'ichi Kobayashi、Eri Fukushi、Jun Kawabata、Tomoko Ozawa、Atsunori Masuda、Yoshiaki Kitaya、Kenji Omasa

  DOI：10.1021/jo702440s

  日期：2008.2.1

  A 15-membered macrolide, iriomoteolide-3a (1), with an allyl epoxide has been isolated from a marine benthic dinoflagellate Amphidinium sp. (strain HYA024), and the structure was assigned by detailed analyses of 2D NMR data. Relative and absolute configurations were elucidated on the basis of conformational studies of 1 and its acetonide (2) and modified Mosher's method of 1, respectively. Iriomoteolide3a (1) and the acetonide (2) exhibited potently cytotoxic activity against antitumor cells.