methyl (E)-2'-isocyanato-3'-methoxycinnamate | 155710-67-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-2'-isocyanato-3'-methoxycinnamate
• CAS: 155710-67-1
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: NOKAXVMQJYDICA-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-2'-isocyanato-3'-methoxycinnamate 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 51.0h， 生成 (4aR*,9R*,9aS*)-4a-acetyl-5-methoxy-9a-methoxycarbonyl-9-methoxycarbonylmethyl-1,2,3,4,4a,9,9a,10-octahydroacridine
  参考文献：
  名称：

  A highly diastereoselective tandem Michael-Michael addition reaction in a rotameric ring system: steric acceleration due to conformation locking

  摘要：

  A highly diastereoselective one-pot tandem Michael-Michael addition reaction developed in a rotamerically locked conformation is described. Reaction of isocyanates 8 - 13 with hydroxylactone 14 gave tandem Michael-Michael adducts 22 - 26 in good to excellent yields. The intermediate tricyclic oxazolidinones consisted of rotamer pairs 16 - 19, and the rotation barriers of some of these compounds were determined. The tandem addition reaction was highly accelerated by introducing conformation anchoring group X. A new versatile synthesis of octahydroacridines 27 - 29 using the tandem adducts is also described.

  DOI：

  10.1016/s0040-4020(01)80175-7
• 作为产物：
  描述：

  光气 、 以 甲苯 为溶剂， 以84%的产率得到methyl (E)-2'-isocyanato-3'-methoxycinnamate
  参考文献：
  名称：

  A highly diastereoselective tandem Michael-Michael addition reaction in a rotameric ring system: steric acceleration due to conformation locking

  摘要：

  A highly diastereoselective one-pot tandem Michael-Michael addition reaction developed in a rotamerically locked conformation is described. Reaction of isocyanates 8 - 13 with hydroxylactone 14 gave tandem Michael-Michael adducts 22 - 26 in good to excellent yields. The intermediate tricyclic oxazolidinones consisted of rotamer pairs 16 - 19, and the rotation barriers of some of these compounds were determined. The tandem addition reaction was highly accelerated by introducing conformation anchoring group X. A new versatile synthesis of octahydroacridines 27 - 29 using the tandem adducts is also described.

  DOI：

  10.1016/s0040-4020(01)80175-7