1-Benzyl-2-methoxymethyl-aziridine-2-carboxylic acid benzyl-[(Z)-6-(4-methoxy-benzyloxy)-hex-3-enyl]-amide | 220456-13-3

• 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: 1-Benzyl-2-methoxymethyl-aziridine-2-carboxylic acid benzyl-[(Z)-6-(4-methoxy-benzyloxy)-hex-3-enyl]-amide
• 英文别名: N,1-dibenzyl-2-(methoxymethyl)-N-[(Z)-6-[(4-methoxyphenyl)methoxy]hex-3-enyl]aziridine-2-carboxamide
• CAS: 220456-13-3
• 化学式: C₃₃H₄₀N₂O₄
• 分子量: 528.692
• InChiKey: JFMMJBBOZGFBPM-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Benzyl-2-methoxymethyl-aziridine-2-carboxylic acid benzyl-[(Z)-6-(4-methoxy-benzyloxy)-hex-3-enyl]-amide 以 邻二氯苯 为溶剂， 反应 2.5h， 以59%的产率得到(3R,3aS,7aS)-1,6-Dibenzyl-3-[2-(4-methoxy-benzyloxy)-ethyl]-7a-methoxymethyl-octahydro-pyrrolo[2,3-c]pyridin-7-one
  参考文献：
  名称：

  Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic Rings

  摘要：

  Studies have been conducted on testing strategies for annulation of the two macrocyclic rings onto the central tricyclic nucleus of sarain A (1). In particular, methodology has been developed for introduction into the core of C-3' and C-3 substituents, which are necessary for construction of the "eastern" and "western" macrocyclic rings of I, respectively. Formation of the western ring has been successfully addressed via a ring-closing olefin metathesis strategy utilizing the Grubbs ruthenium catalyst. With this macrocyclization approach, a key intermediate lactam has been prepared which will be utilized in a total synthesis of the natural product.

  DOI：

  10.1021/jo981821d
• 作为产物：
  描述：

  1-Benzyl-2-methoxymethyl-aziridine-2-carboxylic acid methyl ester 在 三甲基铝 、 lithium hexamethyldisilazane 作用下， 反应 2.58h， 生成 1-Benzyl-2-methoxymethyl-aziridine-2-carboxylic acid benzyl-[(Z)-6-(4-methoxy-benzyloxy)-hex-3-enyl]-amide
  参考文献：
  名称：

  Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic Rings

  摘要：

  Studies have been conducted on testing strategies for annulation of the two macrocyclic rings onto the central tricyclic nucleus of sarain A (1). In particular, methodology has been developed for introduction into the core of C-3' and C-3 substituents, which are necessary for construction of the "eastern" and "western" macrocyclic rings of I, respectively. Formation of the western ring has been successfully addressed via a ring-closing olefin metathesis strategy utilizing the Grubbs ruthenium catalyst. With this macrocyclization approach, a key intermediate lactam has been prepared which will be utilized in a total synthesis of the natural product.

  DOI：

  10.1021/jo981821d