哥纳香素 | 113817-64-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 哥纳香素
• 英文名称: goniothalamicin
• 英文别名: 2(5H)-Furanone, 5-methyl-3-(2,8,11-trihydroxy-11-(tetrahydro-5-(1-hydroxypentadecyl)-2-furanyl)undecyl)-；(2S)-2-methyl-4-[(2R,8R,11R)-2,8,11-trihydroxy-11-[(2R,5R)-5-[(1R)-1-hydroxypentadecyl]oxolan-2-yl]undecyl]-2H-furan-5-one
• CAS: 113817-64-4
• 化学式: C₃₅H₆₄O₇
• 分子量: 596.889
• InChiKey: NBVJDUCRUAUMAA-CGWDHHCXSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  751.0±55.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  42
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二甲基亚砜 、 哥纳香素 在 三甲基氯硅烷 作用下， 生成 Goniothalamicin 10,13-formaldehyde acetal
  参考文献：
  名称：

  Determining Absolute Configurations of Stereocenters in Annonaceous Acetogenins through Formaldehyde Acetal Derivatives and Mosher Ester Methodology

  摘要：

  Formaldehyde (methylene) acetal derivatives can be conveniently prepared, on a small scale, using parent Annonaceous acetogenins which have 1,2-, 1,4-, and/or 1,5-diols along their aliphatic chains. The resulting cyclic acetal protons give NMR signals which allow characterization of the relative stereochemistries of the two stereogenic centers that originated from the diols. Less complicated (vs the parent acetogenins) per-Mosher ester [methoxy(trifluoromethyl)phenyl acetate or MTPA] derivatives of the acetal derivatives can then be prepared and used to determine absolute configurations of the chiral positions which bear the remaining free hydroxyls. Prior knowledge of relative stereochemical relationships then permits assignments of absolute configurations to additional chiral centers along the chain of the molecules. This method has been particularly useful in solving the absolute configurations of several nonadjacent bis-THF and mono-THF acetogenins, viz. bullatanocin (1), (2,4-cis and trans)-bullatanocinones (2 and 3), bullatalicin (4), (2,4-cis and trans)-bullatalicinones (5 and 6), squamostatin A (7), squamocin (8), gigantetrocin A (9), and goniothalamicin (10). Most of the resulting acetals (vs the parent acetogenins) show enhanced, bioactivities, and their mode of action is, likewise, by mitochondrial inhibition.

  DOI：

  10.1021/jo00097a017
• 作为产物：
  描述：

  (+)-giganin 在 间氯过氧苯甲酸 作用下， 反应 2.0h， 生成 gigantetrocin A 、 哥纳香素 、 (S)-3-{(R)-2-Hydroxy-7-[(2R,5R)-5-((1R,4R,5R)-1,4,5-trihydroxy-nonadecyl)-tetrahydro-furan-2-yl]-heptyl}-5-methyl-5H-furan-2-one 、 (S)-5-Methyl-3-{(2R,8R,11S)-2,8,11-trihydroxy-11-[(2S,5R)-5-((R)-1-hydroxy-pentadecyl)-tetrahydro-furan-2-yl]-undecyl}-5H-furan-2-one
  参考文献：
  名称：

  Absolute Stereochemistries of Giganin and Longanin, Bioactive Non-tetrahydrofuran Ring Annonaceous Acetogenins from Asimina longifolia

  摘要：

  DOI：

  10.3987/com-96-7515

文献信息

• Absolute Stereochemistries of Giganin and Longanin, Bioactive Non-tetrahydrofuran Ring Annonaceous Acetogenins from Asimina longifolia
  作者：Jerry L. McLaughlin、Qing Ye、Dean Evert

  DOI：10.3987/com-96-7515

  日期：——
• Determining Absolute Configurations of Stereocenters in Annonaceous Acetogenins through Formaldehyde Acetal Derivatives and Mosher Ester Methodology
  作者：Z. Gu、Lu Zeng、X. Fang、Trina Colman-Saizarbitoria、Mei Huo、Jerry L. McLaughlin

  DOI：10.1021/jo00097a017

  日期：1994.9

  Formaldehyde (methylene) acetal derivatives can be conveniently prepared, on a small scale, using parent Annonaceous acetogenins which have 1,2-, 1,4-, and/or 1,5-diols along their aliphatic chains. The resulting cyclic acetal protons give NMR signals which allow characterization of the relative stereochemistries of the two stereogenic centers that originated from the diols. Less complicated (vs the parent acetogenins) per-Mosher ester [methoxy(trifluoromethyl)phenyl acetate or MTPA] derivatives of the acetal derivatives can then be prepared and used to determine absolute configurations of the chiral positions which bear the remaining free hydroxyls. Prior knowledge of relative stereochemical relationships then permits assignments of absolute configurations to additional chiral centers along the chain of the molecules. This method has been particularly useful in solving the absolute configurations of several nonadjacent bis-THF and mono-THF acetogenins, viz. bullatanocin (1), (2,4-cis and trans)-bullatanocinones (2 and 3), bullatalicin (4), (2,4-cis and trans)-bullatalicinones (5 and 6), squamostatin A (7), squamocin (8), gigantetrocin A (9), and goniothalamicin (10). Most of the resulting acetals (vs the parent acetogenins) show enhanced, bioactivities, and their mode of action is, likewise, by mitochondrial inhibition.