methyl (2S)-2-[[(Z)-[7-[(8Z)-1,6-dihydroxy-8-[[[(2S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]amino]methylidene]-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-2-oxo-4-propan-2-ylnaphthalen-1-ylidene]methyl]amino]-3-(1H-indol-3-yl)propanoate

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl (2S)-2-[[(Z)-[7-[(8Z)-1,6-dihydroxy-8-[[[(2S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]amino]methylidene]-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-2-oxo-4-propan-2-ylnaphthalen-1-ylidene]methyl]amino]-3-(1H-indol-3-yl)propanoate
• 化学式: C₅₄H₅₄N₄O₁₀
• 分子量: 919.044
• InChiKey: KTNGHLCZVVDFRG-CDZRQLLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  68.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  223.3
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(Z)-[7-[(8Z)-1,6-dihydroxy-8-[[[(2S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]amino]methylidene]-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-2-oxo-4-propan-2-ylnaphthalen-1-ylidene]methyl]amino]-3-(1H-indol-3-yl)propanoate 在 盐酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 (-)-棉子素
  参考文献：
  名称：

  An expedient route for the practical preparation of optically active (−)-gossypol

  摘要：

  A simple and practical procedure has been developed for the resolution of racemic gossypol. The commercially available L-amino acid esters have been employed as the resolving agents with the L-tryptophan methyl ester (L-Trp-OMe) as the best reagent of choice. The individual diastereoisomeric gossypol adducts derived from L-Trp-OMe are readily separated by a simple filtration step to give the (-)-diastereoisomeric adduct, and its (+)-diastereoisomeric adduct can be easily obtained by simple evaporation of the mother liquor. Acid hydrolysis of the separated adduct gave (-)-gossypol and (+)-gossypol, respectively, in high chemical yields (quantitatively) and in high enantiomeric excesses (> 95%). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.032
• 作为产物：
  描述：

  (-)-棉子素 、 L-色氨酸甲酯盐酸盐 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以20.5%的产率得到methyl (2S)-2-[[(Z)-[7-[(8Z)-1,6-dihydroxy-8-[[[(2S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]amino]methylidene]-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-2-oxo-4-propan-2-ylnaphthalen-1-ylidene]methyl]amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  An expedient route for the practical preparation of optically active (−)-gossypol

  摘要：

  A simple and practical procedure has been developed for the resolution of racemic gossypol. The commercially available L-amino acid esters have been employed as the resolving agents with the L-tryptophan methyl ester (L-Trp-OMe) as the best reagent of choice. The individual diastereoisomeric gossypol adducts derived from L-Trp-OMe are readily separated by a simple filtration step to give the (-)-diastereoisomeric adduct, and its (+)-diastereoisomeric adduct can be easily obtained by simple evaporation of the mother liquor. Acid hydrolysis of the separated adduct gave (-)-gossypol and (+)-gossypol, respectively, in high chemical yields (quantitatively) and in high enantiomeric excesses (> 95%). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.032