(S)-3-[7-((2R,5S)-5-{(4S,7R)-7-[(2R,5R)-5-((R)-1-Hydroxy-tridecyl)-tetrahydro-furan-2-yl]-[1,3]dioxepan-4-yl}-tetrahydro-furan-2-yl)-heptyl]-5-methyl-5H-furan-2-one | 195827-76-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-[7-((2R,5S)-5-{(4S,7R)-7-[(2R,5R)-5-((R)-1-Hydroxy-tridecyl)-tetrahydro-furan-2-yl]-[1,3]dioxepan-4-yl}-tetrahydro-furan-2-yl)-heptyl]-5-methyl-5H-furan-2-one
• 英文别名: (2S)-4-[7-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-1,3-dioxepan-4-yl]oxolan-2-yl]heptyl]-2-methyl-2H-furan-5-one
• CAS: 195827-76-0
• 化学式: C₃₈H₆₆O₇
• 分子量: 634.938
• InChiKey: FJNAHVKQVREHDF-VUODRKSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  45
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (S)-3-[7-((2R,5S)-5-{(4S,7R)-7-[(2R,5R)-5-((R)-1-Hydroxy-tridecyl)-tetrahydro-furan-2-yl]-[1,3]dioxepan-4-yl}-tetrahydro-furan-2-yl)-heptyl]-5-methyl-5H-furan-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-[(2R,5R)-5-((4R,7S)-7-{(2S,5R)-5-[7-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-heptyl]-tetrahydro-furan-2-yl}-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-tridecyl ester
  参考文献：
  名称：

  (2,4-cis and trans)-Gigantecinone and 4-Deoxygigantecin, Bioactive Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenins, from Goniothalamus giganteus

  摘要：

  Two new acetogenins, (2,4-cis and trans)-gigantecinone (1), isolated as a mixture, and 4-deoxygigantecin (2), a known acetogenin whose absolute stereochemistry has not been determined previously, were isolated using activity-directed fractionation, from the bark of Goniothalamus giganteus. A key step in solving their absolute stereochemistries was the preparation of 1,4-diol formaldehyde acetal derivatives (1b and 2a). Using the advanced Mosher ester method and circular dichroism, the absolute stereochemistries of I and 2 were revealed and were found to be the same as that of gigantecin (3), which supports a common biogenetic origin. Both 1 and Ib showed potent and selective cytotoxicities against the PC-3 human prostate adenocarcinoma cell line. Against yellow fever mosquito larvae, 1 and 2 were more potent than rotenone in pesticidal activity. Longimicin C and a mixture of (2,4-cis and trans)-isoannonacin were also isolated for the first time from this species.

  DOI：

  10.1021/np970211q
• 作为产物：
  描述：

  二甲基亚砜 、 (+)-4-deoxygigantecin 在 碘代三甲硅烷 作用下， 生成 (S)-3-[7-((2R,5S)-5-{(4S,7R)-7-[(2R,5R)-5-((R)-1-Hydroxy-tridecyl)-tetrahydro-furan-2-yl]-[1,3]dioxepan-4-yl}-tetrahydro-furan-2-yl)-heptyl]-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  (2,4-cis and trans)-Gigantecinone and 4-Deoxygigantecin, Bioactive Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenins, from Goniothalamus giganteus

  摘要：

  Two new acetogenins, (2,4-cis and trans)-gigantecinone (1), isolated as a mixture, and 4-deoxygigantecin (2), a known acetogenin whose absolute stereochemistry has not been determined previously, were isolated using activity-directed fractionation, from the bark of Goniothalamus giganteus. A key step in solving their absolute stereochemistries was the preparation of 1,4-diol formaldehyde acetal derivatives (1b and 2a). Using the advanced Mosher ester method and circular dichroism, the absolute stereochemistries of I and 2 were revealed and were found to be the same as that of gigantecin (3), which supports a common biogenetic origin. Both 1 and Ib showed potent and selective cytotoxicities against the PC-3 human prostate adenocarcinoma cell line. Against yellow fever mosquito larvae, 1 and 2 were more potent than rotenone in pesticidal activity. Longimicin C and a mixture of (2,4-cis and trans)-isoannonacin were also isolated for the first time from this species.

  DOI：

  10.1021/np970211q

文献信息

• (2,4-<i>cis</i> and <i>trans</i>)-Gigantecinone and 4-Deoxygigantecin, Bioactive Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenins, from <i>Goniothalamus giganteus</i>
  作者：Feras Q. Alali、Yan Zhang、Lingling Rogers、J. L. McLaughlin

  DOI：10.1021/np970211q

  日期：1997.9.1

  Two new acetogenins, (2,4-cis and trans)-gigantecinone (1), isolated as a mixture, and 4-deoxygigantecin (2), a known acetogenin whose absolute stereochemistry has not been determined previously, were isolated using activity-directed fractionation, from the bark of Goniothalamus giganteus. A key step in solving their absolute stereochemistries was the preparation of 1,4-diol formaldehyde acetal derivatives (1b and 2a). Using the advanced Mosher ester method and circular dichroism, the absolute stereochemistries of I and 2 were revealed and were found to be the same as that of gigantecin (3), which supports a common biogenetic origin. Both 1 and Ib showed potent and selective cytotoxicities against the PC-3 human prostate adenocarcinoma cell line. Against yellow fever mosquito larvae, 1 and 2 were more potent than rotenone in pesticidal activity. Longimicin C and a mixture of (2,4-cis and trans)-isoannonacin were also isolated for the first time from this species.