tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{{{(1R)-2-hydroxy-1-[4-(prop-2-enyloxy)phenyl]ethyl}amino}methyl}-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 1159576-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{{{(1R)-2-hydroxy-1-[4-(prop-2-enyloxy)phenyl]ethyl}amino}methyl}-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 1159576-35-8
• 化学式: C₂₄H₃₆N₂O₆
• 分子量: 448.56
• InChiKey: DGQRYKLRKRPHOR-JSXRDJHFSA-N

物化性质

• 沸点：
  576.4±50.0 °C(predicted)
• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.49
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{{{(1R)-2-hydroxy-1-[4-(prop-2-enyloxy)phenyl]ethyl}amino}methyl}-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以44%的产率得到(2R,3R,4S)-2-{{[(1R)-2-hydroxy-1-[4'-(prop-2-enyloxy)phenyl]ethyl]amino}methyl}pyrrolidine-3,4-diol
  参考文献：
  名称：

  Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

  摘要：

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.009
• 作为产物：
  描述：

  tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{{{(1R)-2-methoxy-2-oxo-1-[4-(prop-2-enyloxy)phenyl]ethyl}amino}methyl}-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到tert-butyl (3aR,4R,6aS)-2,2-dimethyl-4-{{{(1R)-2-hydroxy-1-[4-(prop-2-enyloxy)phenyl]ethyl}amino}methyl}-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

  摘要：

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.009