顺式-N-Boc-吡咯烷-3,4-二羧酸 | 441298-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 顺式-N-Boc-吡咯烷-3,4-二羧酸
• 英文名称: tert-butoxycarbonyl-cis-pyrrolidine-3,4-dicarboxylic acid
• 英文别名: cis-1-tert-butoxycarbonyl pyrrolidine-3,4-dicarboxylic acid；cis-N-Boc-pyrrolidine-3,4-dicarboxylic acid；(3S,4R)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3,4-dicarboxylic acid
• CAS: 441298-21-1
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: CEWHNBGJGPXFED-KNVOCYPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  顺式-N-Boc-吡咯烷-3,4-二羧酸 在 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到cis-5-tert-butoxycarbonyltetrahydro-3aH-furo[3,4-c]pyrrole-1,3-dione
  参考文献：
  名称：

  Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge

  摘要：

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.004
• 作为产物：
  描述：

  tert-butoxycarbonyl-cis-pyrrolidine-3,4-dicarboxylic benzyl ester 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以92%的产率得到顺式-N-Boc-吡咯烷-3,4-二羧酸
  参考文献：
  名称：

  A mild Boc deprotection and the importance of a free carboxylate

  摘要：

  We report a facile and rapid removal of Boc protecting groups using microwave heating in H2O, With deprotection only requiring a free carboxylic acid group in the starting material. Unlike previous approaches, no additional reagents are required. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.09.027