(1S,2R,7aS)-1,2-dihydroxy-3-pyrrolizidinone | 259235-01-3

• 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: (1S,2R,7aS)-1,2-dihydroxy-3-pyrrolizidinone
• 英文别名: (1S,2R,7aS)-1,2-dihydroxypyrrolizidin-3-one；(1S,2R,8S)-1,2-dihydroxy-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 259235-01-3
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: ADSLGPSVITYQPB-HCWXCVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 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：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,7aS)-1,2-dihydroxy-3-pyrrolizidinone 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (1S,2S,7aS)-1,2-dibenzyloxypyrrolizidine
  参考文献：
  名称：

  Polyhydroxylated pyrrolizidines. Part 5: Stereoselective synthesis of 1,2-dihydroxypyrrolizidines as a model for the preparation of densely polyhydroxylated pyrrolizidines

  摘要：

  The reaction of N-benzyloxycarbonyl-L-prolinal 5 with (methoxycarbonylmethylene)triphenylphosphorane in CH2Cl2 afforded methyl (E)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate 7. When the reaction was performed in MeOH, an appreciable amount of the (Z)-isomer 6 was obtained. Compounds 7 and 6 were dihydroxylated to the corresponding 2,3-dihydroxy esters 8-9 and 20 21, respectively. The stereochemistry of the latter compounds could be determined after their transformations into the corresponding 1,2-dihydroxypyrrolizidin-3-ones 11-16 and 23-25, respectively. Finally, lactams 11, 16, and 25 were reduced to the related pyrrolizidines 14, 19, and 27. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.003
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 palladium on activated charcoal 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 四氧化锇 、 氢气 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 12.0h， 生成 (1S,2R,7aS)-1,2-dihydroxy-3-pyrrolizidinone
  参考文献：
  名称：

  Polyhydroxylated pyrrolizidines. Part 5: Stereoselective synthesis of 1,2-dihydroxypyrrolizidines as a model for the preparation of densely polyhydroxylated pyrrolizidines

  摘要：

  The reaction of N-benzyloxycarbonyl-L-prolinal 5 with (methoxycarbonylmethylene)triphenylphosphorane in CH2Cl2 afforded methyl (E)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate 7. When the reaction was performed in MeOH, an appreciable amount of the (Z)-isomer 6 was obtained. Compounds 7 and 6 were dihydroxylated to the corresponding 2,3-dihydroxy esters 8-9 and 20 21, respectively. The stereochemistry of the latter compounds could be determined after their transformations into the corresponding 1,2-dihydroxypyrrolizidin-3-ones 11-16 and 23-25, respectively. Finally, lactams 11, 16, and 25 were reduced to the related pyrrolizidines 14, 19, and 27. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.003

文献信息

• Samarium Diiodide-Promoted Cyclization of <i>N</i>-(ω-Iodoalkyl)imides to Polyhydroxylated Indolizidinones and Pyrrolizidinones:  Synthesis of (+)-Lentiginosine
  作者：Deok-Chan Ha、Chang-Soo Yun、Yeonbae Lee

  DOI：10.1021/jo9913762

  日期：2000.1.1
• Polyhydroxylated pyrrolizidines. Part 5: Stereoselective synthesis of 1,2-dihydroxypyrrolizidines as a model for the preparation of densely polyhydroxylated pyrrolizidines
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Juan A. Tamayo

  DOI：10.1016/j.tetasy.2004.10.003

  日期：2004.11

  The reaction of N-benzyloxycarbonyl-L-prolinal 5 with (methoxycarbonylmethylene)triphenylphosphorane in CH2Cl2 afforded methyl (E)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate 7. When the reaction was performed in MeOH, an appreciable amount of the (Z)-isomer 6 was obtained. Compounds 7 and 6 were dihydroxylated to the corresponding 2,3-dihydroxy esters 8-9 and 20 21, respectively. The stereochemistry of the latter compounds could be determined after their transformations into the corresponding 1,2-dihydroxypyrrolizidin-3-ones 11-16 and 23-25, respectively. Finally, lactams 11, 16, and 25 were reduced to the related pyrrolizidines 14, 19, and 27. (C) 2004 Elsevier Ltd. All rights reserved.