Ethyl 16-acetyl-15-thiatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-16-carboxylate | 182313-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Ethyl 16-acetyl-15-thiatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-16-carboxylate
• CAS: 182313-29-7
• 化学式: C₂₀H₁₈O₃S
• 分子量: 338.427
• InChiKey: VPNDMEMMRCPLSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 16-acetyl-15-thiatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-16-carboxylate 在 羟胺 作用下， 以85%的产率得到
  参考文献：
  名称：

  Glycosyl Transfer to Nitrogen via Cycloaddition

  摘要：

  [GRAPHICS]This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.

  DOI：

  10.1021/ol990583l
• 作为产物：
  描述：

  蒽 、 Ethyl 2-(1,3-dioxoisoindol-2-yl)sulfanyl-3-oxobutanoate 在 吡啶 作用下， 以90%的产率得到Ethyl 16-acetyl-15-thiatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-16-carboxylate
  参考文献：
  名称：

  Glycosyl Transfer to Nitrogen via Cycloaddition

  摘要：

  [GRAPHICS]This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.

  DOI：

  10.1021/ol990583l

文献信息

• α-Oxosulfines part 1: Reactivity of α-oxosulfines obtained from Retro Diels-Alder reaction of 1,4-oxathiin-S-oxides
  作者：Giuseppe Capozzi、Paola Fratini、Stefano Menichetti、Cristina Nativi

  DOI：10.1016/0040-4020(96)00710-7

  日期：1996.9

  Retro Diels-Alder (RDA) reaction to form α-oxosulfines under very mild conditions. These reactive intermediates can be successfully trapped as dienophiles or as electron poor dienes in Inverse Electron Demand Diels-Alder reaction (IEDDA). The relationship between the structure of the starting sulfoxide, the geometry of the intermediate sulfine and the stereochemistry of the final cycloadduct have been

  1,4-氧杂ath啶衍生物10–16的氧化可提供高产率和良好的立体选择性的相应亚砜17–26。所述oxathiin-小号-oxides经历逆狄尔斯-阿尔德（RDA）反应以形成α-oxosulfines非常温和的条件下。这些反应性中间体可以成功地捕获为亲电子体或逆电子需量狄尔斯-阿尔德反应（IEDDA）中的贫电子二烯。起始亚砜的结构，中间亚砜的几何形状和最终环加合物的立体化学之间的关系已被初步关联。
• Glycosyl Transfer to Nitrogen via Cycloaddition
  作者：Baoqing Li、Richard W. Franck、Giuseppe Capozzi、Stefano Menichetti、Cristina Nativi

  DOI：10.1021/ol990583l

  日期：1999.7.1

  [GRAPHICS]This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.