[(3S,5S,8R,9S,10S,12R,13S,14S,16S,17R)-12-acetyloxy-16-[(5,5-dimethyl-3,4-dihydropyrrol-2-yl)oxy]-17-(1-iodoethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate | 1446685-91-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(3S,5S,8R,9S,10S,12R,13S,14S,16S,17R)-12-acetyloxy-16-[(5,5-dimethyl-3,4-dihydropyrrol-2-yl)oxy]-17-(1-iodoethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1446685-91-1
• 化学式: C₃₁H₄₈INO₅
• 分子量: 641.63
• InChiKey: YLZZSSBEXYZXAG-CSTLQKIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S,5S,8R,9S,10S,12R,13S,14S,16S,17R)-12-acetyloxy-16-[(5,5-dimethyl-3,4-dihydropyrrol-2-yl)oxy]-17-(1-iodoethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以88%的产率得到[(3S,5S,8R,9S,10S,12R,13S,14S,16S,17R)-12-acetyloxy-16-[(5,5-dimethyl-3,4-dihydropyrrol-2-yl)oxy]-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  参考文献：
  名称：

  Unexpected opening of steroidal E-ring during hypoiodite-mediated oxidation

  摘要：

  In this Letter, we report unexpected formation of E-ring opened steroidal alkaloid from primary amine presumably via a hypoiodite-mediated iodoamination followed by fragmentation of sterically congested iodospiroaminal. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.115
• 作为产物：
  描述：

  [(1R,2S,4S,6R,7S,8R,9S,10R,12S,13S,16S,18S)-10-acetyloxy-6-(3-amino-3-methylbutyl)-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] acetate 在 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到[(3S,5S,8R,9S,10S,12R,13S,14S,16S,17R)-12-acetyloxy-16-[(5,5-dimethyl-3,4-dihydropyrrol-2-yl)oxy]-17-(1-iodoethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  参考文献：
  名称：

  Unexpected opening of steroidal E-ring during hypoiodite-mediated oxidation

  摘要：

  In this Letter, we report unexpected formation of E-ring opened steroidal alkaloid from primary amine presumably via a hypoiodite-mediated iodoamination followed by fragmentation of sterically congested iodospiroaminal. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.115