(S)-1-(1H-indol-4-yloxy)-2,3-isopropylidenedioxypropane | 209728-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-1-(1H-indol-4-yloxy)-2,3-isopropylidenedioxypropane
• 英文别名: 4-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-1H-indole
• CAS: 209728-00-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: NPTNLEPXSCGYKX-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(1H-indol-4-yloxy)-2,3-isopropylidenedioxypropane 在 吡啶 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.5h， 生成 2-羟基-1.3-二苯基-2-(4-甲氧基-苯基)-丙烷
  参考文献：
  名称：

  Synthesis of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4-hydroxypiperidin-1-yl]-propan-2-ol (LY333068) succinate, and its 3-[14C]-isotopomer based on chiral glycerol-[14C] derivatives

  摘要：

  The 3-[C-14]-isotopomer of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4- hydroxypiperidin-1-yl]-propan-2-ol (LY333068), a 5HT(1A) antagonist, was prepared in 10 steps and 8.2% radiochemical yield from (L)-serine-[3-C-14]. Deamination, esterification, and protection of the resulting diet gave methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate-[3-C-14], as a chiral and radiolabeled building block, which then was subsequently coupled with 4-hydroxyindole and 4-(3-methoxyphenyl)-4-hydroxypiperidine to give the titled product with 99.4% radiochemical purity.

  DOI：

  10.1002/(sici)1099-1344(199806)41:6<465::aid-jlcr103>3.0.co;2-b
• 作为产物：
  描述：

  (R)-(-)-甘油醇缩丙酮 在 吡啶 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 4.5h， 生成 (S)-1-(1H-indol-4-yloxy)-2,3-isopropylidenedioxypropane
  参考文献：
  名称：

  Synthesis of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4-hydroxypiperidin-1-yl]-propan-2-ol (LY333068) succinate, and its 3-[14C]-isotopomer based on chiral glycerol-[14C] derivatives

  摘要：

  The 3-[C-14]-isotopomer of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4- hydroxypiperidin-1-yl]-propan-2-ol (LY333068), a 5HT(1A) antagonist, was prepared in 10 steps and 8.2% radiochemical yield from (L)-serine-[3-C-14]. Deamination, esterification, and protection of the resulting diet gave methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate-[3-C-14], as a chiral and radiolabeled building block, which then was subsequently coupled with 4-hydroxyindole and 4-(3-methoxyphenyl)-4-hydroxypiperidine to give the titled product with 99.4% radiochemical purity.

  DOI：

  10.1002/(sici)1099-1344(199806)41:6<465::aid-jlcr103>3.0.co;2-b

文献信息

• Synthesis of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4-hydroxypiperidin-1-yl]-propan-2-ol (LY333068) succinate, and its 3-[14C]-isotopomer based on chiral glycerol-[14C] derivatives
  作者：Boris A. Czeskis

  DOI：10.1002/(sici)1099-1344(199806)41:6<465::aid-jlcr103>3.0.co;2-b

  日期：1998.6

  The 3-[C-14]-isotopomer of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4- hydroxypiperidin-1-yl]-propan-2-ol (LY333068), a 5HT(1A) antagonist, was prepared in 10 steps and 8.2% radiochemical yield from (L)-serine-[3-C-14]. Deamination, esterification, and protection of the resulting diet gave methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate-[3-C-14], as a chiral and radiolabeled building block, which then was subsequently coupled with 4-hydroxyindole and 4-(3-methoxyphenyl)-4-hydroxypiperidine to give the titled product with 99.4% radiochemical purity.