(Z)-N-(2-iodovinyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide | 1334510-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-N-(2-iodovinyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide
• 英文别名: N-[(Z)-2-iodoethenyl]-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide
• CAS: 1334510-08-5
• 化学式: C₁₁H₁₈INO₃
• 分子量: 339.173
• InChiKey: GINFPUFJPNXUAA-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N-(2-iodovinyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2,2,5,5-tetramethyl-1,3-dioxan-4-yl)oxazole 、
  参考文献：
  名称：

  Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides

  摘要：

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.

  DOI：

  10.1021/jo202130e
• 作为产物：
  描述：

  N-(2,2-diiodovinyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide 在 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以71%的产率得到(Z)-N-(2-iodovinyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide
  参考文献：
  名称：

  Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides

  摘要：

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.

  DOI：

  10.1021/jo202130e

文献信息

• Regioselective synthesis of β-iodo-enamides and β-yn-enamides
  作者：Adele E. Pasqua、Lynne H. Thomas、James J. Crawford、Rodolfo Marquez

  DOI：10.1016/j.tet.2011.07.033

  日期：2011.9

  Iodo-enamides were synthesised in a single step, in good yield and with complete selectivity from N-formyl imides. The beta-iodo-enamides are stable and were converted efficiently into novel geometrically defined beta-yn-enamides. (C) 2011 Elsevier Ltd. All rights reserved.