tert-butyl 2-diazo-3,6-dioxotridec-11-ynoate | 529508-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2-diazo-3,6-dioxotridec-11-ynoate
• 英文别名: 2-diazonio-1-[(2-methylpropan-2-yl)oxy]-1,6-dioxotridec-2-en-11-yn-3-olate
• CAS: 529508-12-1
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: FENKJEROARAAMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-diazo-3,6-dioxotridec-11-ynoate 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 作用下， 以 正己烷 为溶剂， 生成 8-carbo tert-butoxy-7-methyl-12-oxatricyclo[5.4.1.0^1,6]dodec-6-en-9-one 、 8-carbo tert-butoxy-7-methyl-12-oxatricyclo[5.4.1.0^1,6]dodec-6-en-9-one
  参考文献：
  名称：

  The Scope of Catalytic Enantioselective Tandem Carbonyl Ylide Formation−Intramolecular [3 + 2] Cycloadditions

  摘要：

  Catalytic enantioselective tandem carbonyl ylide formation-intramolecular 1,3-dipolar cycloaddition reactions of 2-diazo-3,6-diketoesters show promising scope in terms of asymmetric induction as the tethered alkene/alkyne dipolarophile component is varied. Cycloadditions were found to occur in moderate to very good yields, with a difference in ee exhibited by the electronically different 2-diazo-3,6-diketoesters 1, 25 and 33, 34. Values for ee of up to 90% for alkene dipolarophiles and up to 86% for alkyne dipolarophiles were obtained.

  DOI：

  10.1021/jo0343735
• 作为产物：
  描述：

  4-oxoundec-9-ynoic acid 在 4-乙酰氨基苯磺酰叠氮 、 二丁基镁 、 三乙胺 作用下， 以 四氢呋喃 、 正庚烷 、 乙腈 为溶剂， 反应 25.5h， 生成 tert-butyl 2-diazo-3,6-dioxotridec-11-ynoate
  参考文献：
  名称：

  The Scope of Catalytic Enantioselective Tandem Carbonyl Ylide Formation−Intramolecular [3 + 2] Cycloadditions

  摘要：

  Catalytic enantioselective tandem carbonyl ylide formation-intramolecular 1,3-dipolar cycloaddition reactions of 2-diazo-3,6-diketoesters show promising scope in terms of asymmetric induction as the tethered alkene/alkyne dipolarophile component is varied. Cycloadditions were found to occur in moderate to very good yields, with a difference in ee exhibited by the electronically different 2-diazo-3,6-diketoesters 1, 25 and 33, 34. Values for ee of up to 90% for alkene dipolarophiles and up to 86% for alkyne dipolarophiles were obtained.

  DOI：

  10.1021/jo0343735

文献信息

• Hodgson, David M.; Labande, Agnès H.; Pierard, Françoise Y. T. M., Synlett, 2003, # 1, p. 59 - 62
  作者：Hodgson, David M.、Labande, Agnès H.、Pierard, Françoise Y. T. M.

  DOI：——

  日期：——