cis-4-benzyl-10-oxa-4-azatricyclo<5.2.1.0>decane-3,5-dione | 7802-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: cis-4-benzyl-10-oxa-4-azatricyclo<5.2.1.0>decane-3,5-dione
• 英文别名: 4-benzyl-10-oxa-4-azatricyclo[5.2.1.0^2,6]decane-3,5-dione；exo-cis-7-Oxa-bicyclo<2.2.1>heptan-dicarbonsaeure-(2,3)-benzylimid；2-benzyl-(3at,7at)-hexahydro-4r,7c-epioxido-isoindole-1,3-dione；(3aR,4S,7R,7aS)-2-benzyl-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 7802-31-5
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: YFPFCGVFKLMZHJ-MPZDIEGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-4-benzyl-10-oxa-4-azatricyclo<5.2.1.0>decane-3,5-dione 在 α,α-diphenyl-L-prolinol borane 硫酸 、 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (1R,2S,5R,6R,7S)-4-Benzyl-5-ethoxy-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]decan-3-one
  参考文献：
  名称：

  Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides

  摘要：

  A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.

  DOI：

  10.1016/s0040-4039(00)79972-2
• 作为产物：
  描述：

  endothall 在 乙酰氯 作用下， 反应 9.5h， 生成 cis-4-benzyl-10-oxa-4-azatricyclo<5.2.1.0>decane-3,5-dione
  参考文献：
  名称：

  Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

  摘要：

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00154-7

文献信息

• Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation
  作者：Timothy A. Hill、Scott G. Stewart、Stephen P. Ackland、Jayne Gilbert、Benjamin Sauer、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.bmc.2007.06.034

  日期：2007.9

  A range of amines was reacted with norcantharidin (2) to provide the corresponding norcantharimides (9-43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (20) which was amenable to epoxidation (mCPBA, 22) and subsequent ring opening (MeOH/H(+); 23) or alternatively, osmylation (OsO(4)/NMO; 24). These simple synthetic modifications of 2 facilitated the

  使一定范围的胺与降冰毒烷素（2）反应以提供相应的降冰毒胺（9-43）。用烯丙胺处理降冰草烷素得到相应的烯丙基-去甲癸酰胺（20），其适合于环氧化（mCPBA，22）和随后的开环（MeOH / H（+）； 23）或可进行的osmylation（OsO（4）/ NMO； N / O）。 24）。这些对2的简单合成修饰促进了一系列新的降冰片内酰胺类化合物的开发，它们显示出对HT29和SW480（结直肠癌）的中等至良好的广谱细胞毒性。MCF-7（乳腺腺癌）；A2780（卵巢癌）; H460（肺癌）；A431（表皮样癌）；DU145（前列腺癌）; BE2-C（神经母细胞瘤）；和SJ-G2（胶质母细胞瘤）。具有C（10）的类比，
• Bicyclic Imides and Isoindolines¹
  作者：Charles H. Grogan、Leonard M. Rice

  DOI：10.1021/jm00342a042

  日期：1963.11
• Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides
  作者：Martin Ostendorf、Romeo Romagnoli、Isabel Cabeza Pereiro、Eric C. Roos、Marinus J. Moolenaar、W.Nico Speckamp、Henk Hiemstra

  DOI：10.1016/s0957-4166(97)00154-7

  日期：1997.6

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.
• Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides
  作者：Romeo Romagnoli、Eric C. Roos、Henk Hiemstra、Marinus J. Moolenaar、W. Nico Speckamp、Bernard Kaptein、Hans E. Schoemaker

  DOI：10.1016/s0040-4039(00)79972-2

  日期：1994.2

  A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.