(1R,2S,6R,7aR)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one | 1604804-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (1R,2S,6R,7aR)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one
• 英文别名: (1R,2S,6R,8R)-1,2,6-trihydroxy-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 1604804-42-3
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: HESYNJWUSQYCCC-KAZBKCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,6R,7aR)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到(1R,2R,6R,7aR)-1,2,6-trihydroxyhexahydro-1H-pyrrolizine-1,2,6-triol
  参考文献：
  名称：

  An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

  摘要：

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.050
• 作为产物：
  描述：

  顺式-4-羟基-D-脯氨酸 在 三乙烯二胺 、 盐酸 、 氯化亚砜 、 二异丁基氢化铝 、 碳酸氢钠 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 108.83h， 生成 (1R,2S,6R,7aR)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one
  参考文献：
  名称：

  An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

  摘要：

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.050

文献信息

• An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines
  作者：Kristerson R. Luna-Freire、João Paulo S. Scaramal、Jackson A.L.C. Resende、Cláudio F. Tormena、Fábio L. Oliveira、Ricardo Aparicio、Fernando Coelho

  DOI：10.1016/j.tet.2013.10.050

  日期：2014.5

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.