cis-5-benzyltetrahydro-1H-furo[3,4-c]pyrrole-1,3(3aH)-dione | 1221289-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: cis-5-benzyltetrahydro-1H-furo[3,4-c]pyrrole-1,3(3aH)-dione
• 英文别名: cis-5-benzyltetrahydro-3aH-furo[3,4-c]pyrrole-1,3-dione；1H-Furo[3,4-c]pyrrole-1,3(3aH)-dione, tetrahydro-5-(phenylmethyl)-, (3aR,6aS)-rel-；(3aR,6aS)-5-benzyl-3a,4,6,6a-tetrahydrofuro[3,4-c]pyrrole-1,3-dione
• CAS: 1221289-17-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: PMPSADXJSJCNFQ-PHIMTYICSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  392.5±35.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-5-benzyltetrahydro-1H-furo[3,4-c]pyrrole-1,3(3aH)-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以74%的产率得到顺式-（1-苄基吡咯烷-3,4-二基）二甲醇
  参考文献：
  名称：

  3-Oxa-7-氮杂双环[3.3.0]辛烷的一种方法—双环吗啉代用品

  摘要：

  摘要 报道了一种3-氧杂-7-氮杂双环[3.3.0]辛烷，双环吗啉类似物的方法，该方法依赖于[3 + 2]马来酸酐或呋喃-2（5 H）-环和原位环加成。生成甲亚胺叶立德。该方法的实用性在多克尺度上得到了证明。 报道了一种3-氧杂-7-氮杂双环[3.3.0]辛烷，双环吗啉类似物的方法，该方法依赖于[3 + 2]马来酸酐或呋喃-2（5 H）-环和原位环加成。生成甲亚胺叶立德。该方法的实用性在多克尺度上得到了证明。

  DOI：

  10.1055/s-0036-1588785
• 作为产物：
  描述：

  1-benzylpyrrolidine-3,4-dicarboxylic acid 在 乙酸酐 、 溶剂黄146 作用下， 以91%的产率得到cis-5-benzyltetrahydro-1H-furo[3,4-c]pyrrole-1,3(3aH)-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

文献信息

• Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
  作者：Ali Thaqi、Janet L. Scott、Jayne Gilbert、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.ejmech.2010.01.004

  日期：2010.5

  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.
• An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates
  作者：Oleksandr Grygorenko、Yevhenii Sokolenko、Eugeniy Ostapchuk、Artem Artemenko

  DOI：10.1055/s-0036-1588785

  日期：2017.7

  bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5H)-ones and an in situ generated azomethine ylide. The utility of the method was demonstrated on a multigram scale. An approach to 3-oxa-7-azabicyclo[3.3.0]octanes, bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5H)-ones and an in

  摘要 报道了一种3-氧杂-7-氮杂双环[3.3.0]辛烷，双环吗啉类似物的方法，该方法依赖于[3 + 2]马来酸酐或呋喃-2（5 H）-环和原位环加成。生成甲亚胺叶立德。该方法的实用性在多克尺度上得到了证明。 报道了一种3-氧杂-7-氮杂双环[3.3.0]辛烷，双环吗啉类似物的方法，该方法依赖于[3 + 2]马来酸酐或呋喃-2（5 H）-环和原位环加成。生成甲亚胺叶立德。该方法的实用性在多克尺度上得到了证明。