(R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine | 1376622-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine
• CAS: 1376622-85-3
• 化学式: C₂₆H₂₈INO₂
• 分子量: 513.418
• InChiKey: FJGVVZFSZIPLQD-UJTWYAIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0~30.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 (R,R,R,R)-2-(4'-methoxyphenyl)-3-acetoxy-4-benzyloxy-5-methylpyrrolidine
  参考文献：
  名称：

  Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine

  摘要：

  Ring-closing iodoamination of (E)-configured, N-alpha-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with 12 and NaHCO3 in MeCN occurs with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.045
• 作为产物：
  描述：

  (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以41%的产率得到(R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine
  参考文献：
  名称：

  Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine

  摘要：

  Ring-closing iodoamination of (E)-configured, N-alpha-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with 12 and NaHCO3 in MeCN occurs with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.045