(Z)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate | 820994-17-0

• 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: (Z)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate
• 英文别名: benzyl (2S)-2-[(Z)-3-methoxy-3-oxoprop-1-enyl]pyrrolidine-1-carboxylate
• CAS: 820994-17-0
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: QREMKCXTGGXQIG-CMUBDUJZSA-N

物化性质

• 沸点：
  411.1±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  非对映选择性环氧化顺式-4-氨基烯丙基醇与米氯过苯甲酸。他汀的有效合成

  摘要：

  广志弘

  DOI：

  10.1039/c39870000311
• 作为产物：
  描述：

  Z-L-脯氨醇 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (Z)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate
  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

• GABA-UPTAKE-INHIBITOREN MIT PYRROLIDINSTRUKTUR
  申请人：BDD Berolina Drug Development AB

  公开号：EP1109783A2

  公开（公告）日：2001-06-27
• [DE] GABA-UPTAKE-INHIBITOREN MIT PYRROLIDINSTRUKTUR<br/>[EN] GABA UPTAKE INHIBITORS HAVING A PYRROLIDINE STRUCTURE<br/>[FR] INHIBITEURS D'ABSORPTION DE GABA A STRUCTURE PYRROLIDINIQUE
  申请人：WANNER KLAUS

  公开号：WO2000014064A2

  公开（公告）日：2000-03-16

  Beschrieben werden Verbindungen der allgemeinen Formel (I), worin R?1 bis R7, A1, A2¿, X und Z wie in Anspruch 1 definiert sind. Diese Verbindungen eignen sich als GABA-uptake-Inhibitoren zur Behandlung von Krankheiten wie beispielsweise Epilepsie.
• Diastereoselective epoxidation of cis-4-amino allylic alcohol with m-chloroperbenzoic acid. An efficient synthesis of statine
  作者：Takahide Nishi

  DOI：10.1039/c39870000311

  日期：——

  Hiroshi Kogen

  广志弘
• 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.