(E)-(4R,5R)-1-pyrrolidino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one | 1258388-25-8

• 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: (E)-(4R,5R)-1-pyrrolidino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one
• 英文别名: (E,4R,5R)-5-hydroxy-4,6-bis[(4-methoxyphenyl)methoxy]-1-pyrrolidin-1-ylhex-1-en-3-one
• CAS: 1258388-25-8
• 化学式: C₂₆H₃₃NO₆
• 分子量: 455.551
• InChiKey: ZONVIISVHGMSRP-WDXRYWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 3,4,6-tri-O-(p-methoxybenzyl)-D-glucal 在 羟基甲苯磺酰碘苯 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以57%的产率得到(E)-(4R,5R)-1-pyrrolidino-5-hydroxy-4,6-O-bis(4-methoxybenzyl)-hex-1-en-3-one
  参考文献：
  名称：

  An efficient one-pot synthesis of β-enamino ketones from endo glucal via hypervalent iodine

  摘要：

  beta-Enamino ketones were successfully synthesized by reaction of endo glycals with primary or secondary amines in the presence of hypervalent iodine reagent in one pot. After the oxidation and protonation taking place on hypervalent iodine agent in acidic condition, endo glucals were effectively converted into the uncyclic beta-alkoxyvinyl ketones. Further substitution of beta-alkoxyvinyl ketones with primary or secondary amines provided the corresponding beta-enamino ketone derivatives in 57-67% yields. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.019

文献信息

• An efficient one-pot synthesis of β-enamino ketones from endo glucal via hypervalent iodine
  作者：Zi-Ping Lin、Hsu-Hsuan Wu、Masayuki Kimura、Kimiyoshi Kaneko、Hiroyuki Takayama、Fung Fuh Wong、Jin Bin Wu、Hui-Chang Lin

  DOI：10.1016/j.tetlet.2010.09.019

  日期：2010.11

  beta-Enamino ketones were successfully synthesized by reaction of endo glycals with primary or secondary amines in the presence of hypervalent iodine reagent in one pot. After the oxidation and protonation taking place on hypervalent iodine agent in acidic condition, endo glucals were effectively converted into the uncyclic beta-alkoxyvinyl ketones. Further substitution of beta-alkoxyvinyl ketones with primary or secondary amines provided the corresponding beta-enamino ketone derivatives in 57-67% yields. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.