methyl (E)-3'-chloro-2'-isocyanatocinnamate | 155710-68-2

• 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)-3'-chloro-2'-isocyanatocinnamate
• 英文别名: methyl (E)-3-(3-chloro-2-isocyanatophenyl)prop-2-enoate
• CAS: 155710-68-2
• 化学式: C₁₁H₈ClNO₃
• 分子量: 237.642
• InChiKey: SDUSPWBBYPYXJE-AATRIKPKSA-N

物化性质

• 沸点：
  347.7±37.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3'-chloro-2'-isocyanatocinnamate 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 19.0h， 生成 (4aR*,9R*,9aS*)-4a-acetyl-5-chloro-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 、 (E)-3-(2-Amino-3-chloro-phenyl)-acrylic acid methyl ester; hydrochloride 以 甲苯 为溶剂， 以52%的产率得到methyl (E)-3'-chloro-2'-isocyanatocinnamate
  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

文献信息

• A highly diastereoselective tandem Michael-Michael addition reaction in a rotameric ring system: steric acceleration due to conformation locking
  作者：Kenji Saito、Makoto Yamamoto、Kazutoshi Yamada、Hideo Takagi

  DOI：10.1016/s0040-4020(01)80175-7

  日期：1993.1

  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.