4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid | 220810-56-0

• 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: 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid
• 英文别名: 4-[[(8R,9S,13S,14S,16S,17S)-16-(3-azidopropyl)-13-methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxymethyl]-3-nitrobenzoic acid
• CAS: 220810-56-0
• 化学式: C₃₄H₄₂N₄O₇
• 分子量: 618.73
• InChiKey: NWNXHCZSPGKIPN-YMOKGWTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丙酸 、 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid 在 盐酸 、 三丁基膦 、 碳酸二异丙酯 、 aminomethyl resin 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 N-[3-[(8R,9S,13S,14S,16S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]propyl]propanamide
  参考文献：
  名称：

  Solid-phase synthesis of phenolic steroids: Towards combinatorial libraries of estradiol derivatives

  摘要：

  The 16 beta-(azidopropyl) derivative of estradiol (7) was synthesized and coupled to aminomethyl resin via a photolabile o-nitrobenzyl linker. Condensation of the corresponding iminophosphorane with activated acids successfully gave amides. Photocleavage resulted in good yield recovery of estradiol derivatives 15 and 16 in acceptable purities for biological screening. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02640-9
• 作为产物：
  描述：

  3-[(8R,9S,13S,14S,16S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl]-propan-1-ol 在 吡啶 、 lithium hydroxide 、 sodium azide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-[(8R,9S,13S,14S,16S,17S)-16-(3-Azido-propyl)-13-methyl-17-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxymethyl]-3-nitro-benzoic acid
  参考文献：
  名称：

  Solid-phase synthesis of phenolic steroids: Towards combinatorial libraries of estradiol derivatives

  摘要：

  The 16 beta-(azidopropyl) derivative of estradiol (7) was synthesized and coupled to aminomethyl resin via a photolabile o-nitrobenzyl linker. Condensation of the corresponding iminophosphorane with activated acids successfully gave amides. Photocleavage resulted in good yield recovery of estradiol derivatives 15 and 16 in acceptable purities for biological screening. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02640-9