(2R,3R)-2-(benzyloxy)-3-((4-methoxybenzyl)((R)-1-phenylethyl)amino)butanal | 1376622-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-2-(benzyloxy)-3-((4-methoxybenzyl)((R)-1-phenylethyl)amino)butanal
• CAS: 1376622-77-3
• 化学式: C₂₇H₃₁NO₃
• 分子量: 417.548
• InChiKey: MCDYQABDGFLDGK-LOYIFYEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(benzyloxy)-3-((4-methoxybenzyl)((R)-1-phenylethyl)amino)butanal 、 (4-甲氧基苄基)三苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (3S,4R,αR,Z)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-(4''-methoxybenzyl)-N-(α-methylbenzyl)-amino]pent-1-ene 、 (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-(4''-methoxybenzyl)-N-(α-methylbenzyl)-amino]pent-1-ene
  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：

  tert-butyl (R,R,R)-2-hydroxy-3-[N-(4'-methoxybenzyl)-N-(α-methylbenzyl)amino]butanoate 在 lithium aluminium tetrahydride 、 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 13.33h， 生成 (2R,3R)-2-(benzyloxy)-3-((4-methoxybenzyl)((R)-1-phenylethyl)amino)butanal
  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