ethyl (1S,4S,5S,6S,7S)-4-benzyl-3-[(4-methoxyphenyl)methyl]-6-methyl-2-oxo-3-azatricyclo[5.2.2.01,5]undec-8-ene-6-carboxylate | 934980-02-6

• 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: ethyl (1S,4S,5S,6S,7S)-4-benzyl-3-[(4-methoxyphenyl)methyl]-6-methyl-2-oxo-3-azatricyclo[5.2.2.01,5]undec-8-ene-6-carboxylate
• CAS: 934980-02-6
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: GZFZZJYSPWDVPQ-JAVNRSFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  ethyl (1S,4S,5S,6S,7S)-4-benzyl-3-[(4-methoxyphenyl)methyl]-6-methyl-2-oxo-3-azatricyclo[5.2.2.01,5]undec-8-ene-6-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以98%的产率得到ethyl (4S,5S,6S)-4-benzyl-3-[(4-methoxyphenyl)methyl]-6-methyl-2-oxo-3-azatricyclo[5.2.2.01,5]undecane-6-carboxylate
  参考文献：
  名称：

  Dynamic Diastereoselectivity during Iron Carbonyl Mediated Spirocyclization Reactions

  摘要：

  Dynamic diastereoselectivity during Fe(CO)(3) promoted [6 + 2] ene spirocyclization of 35a and 35b, having a chiral center on the pendent side chain, was investigated and gave rise to products 28a and 28b instead of four possible isomers. From this reaction, two chiral centers are generated, with absolute stereochemistry determined by the double bond geometry and the chiral center already present. 28a/b and the diene product from demetallation of 28a are proposed as potential intermediates for total synthesis of 18-deoxycytochalasin H. Furthermore, a stepwise second cyclization and a tandem double cyclization mediated by the Fe(CO)(3) moiety was investigated.

  DOI：

  10.1021/jo0625608
• 作为产物：
  描述：

  N-(tert-Butoxycarbonyl)-N-(4-methoxybenzyl)-L-phenylalaninal 在 正丁基锂 、 甲基磺酰氯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 29.67h， 生成 ethyl (1S,4S,5S,6S,7S)-4-benzyl-3-[(4-methoxyphenyl)methyl]-6-methyl-2-oxo-3-azatricyclo[5.2.2.01,5]undec-8-ene-6-carboxylate
  参考文献：
  名称：

  Dynamic Diastereoselectivity during Iron Carbonyl Mediated Spirocyclization Reactions

  摘要：

  Dynamic diastereoselectivity during Fe(CO)(3) promoted [6 + 2] ene spirocyclization of 35a and 35b, having a chiral center on the pendent side chain, was investigated and gave rise to products 28a and 28b instead of four possible isomers. From this reaction, two chiral centers are generated, with absolute stereochemistry determined by the double bond geometry and the chiral center already present. 28a/b and the diene product from demetallation of 28a are proposed as potential intermediates for total synthesis of 18-deoxycytochalasin H. Furthermore, a stepwise second cyclization and a tandem double cyclization mediated by the Fe(CO)(3) moiety was investigated.

  DOI：

  10.1021/jo0625608

文献信息

• Dynamic Diastereoselectivity during Iron Carbonyl Mediated Spirocyclization Reactions
  作者：Anthony J. Pearson、Huikai Sun、Xiaolong Wang

  DOI：10.1021/jo0625608

  日期：2007.3.1

  Dynamic diastereoselectivity during Fe(CO)(3) promoted [6 + 2] ene spirocyclization of 35a and 35b, having a chiral center on the pendent side chain, was investigated and gave rise to products 28a and 28b instead of four possible isomers. From this reaction, two chiral centers are generated, with absolute stereochemistry determined by the double bond geometry and the chiral center already present. 28a/b and the diene product from demetallation of 28a are proposed as potential intermediates for total synthesis of 18-deoxycytochalasin H. Furthermore, a stepwise second cyclization and a tandem double cyclization mediated by the Fe(CO)(3) moiety was investigated.