ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate | 852468-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate
• 英文别名: ethyl (Z,4S)-4-[(4-methoxyphenyl)methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-2-methyl-5-phenylpent-2-enoate
• CAS: 852468-43-0
• 化学式: C₂₇H₃₅NO₅
• 分子量: 453.579
• InChiKey: MSHQDGBHADTRNL-SZPSBJAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate 在 tetracarbonyl(triphenylphosphine)iron 十二/十四烷基二甲基氧化胺 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 13.0h， 生成 tert-butyl (2S,3Z)-(4-methoxybenzyl)(4-formyl-1-phenylpent-3-en-2-yl)carbamate
  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：

  methyl (4-methoxybenzoyl)-L-phenylalaninate 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate
  参考文献：
  名称：

  羰基铁促进的[6 + 2]烯型反应过程中的动态动力学拆分

  摘要：

  环己二烯-Fe（CO）3配合物与侧链烯烃的分子内偶联，形成螺内酰胺，使用手性酰胺底物可实现动态动力学拆分，可进行出色的立体控制。

  DOI：

  10.1016/j.tetlet.2005.02.166

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.
• Dynamic kinetic resolution during iron carbonyl promoted [6+2] ene-type reactions
  作者：Anthony J. Pearson、Xiaolong Wang

  DOI：10.1016/j.tetlet.2005.02.166

  日期：2005.4

  Intramolecular coupling of cyclohexadiene–Fe(CO)3 complexes with pendant alkenes, to form spirolactams, proceed with excellent stereocontrol, using chiral amide substrates that lead to dynamic kinetic resolution.

  环己二烯-Fe（CO）3配合物与侧链烯烃的分子内偶联，形成螺内酰胺，使用手性酰胺底物可实现动态动力学拆分，可进行出色的立体控制。