(E)-8,11-dioxotridec-2-enedioic acid 13-tert-butyl ester 1-methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (E)-8,11-dioxotridec-2-enedioic acid 13-tert-butyl ester 1-methyl ester
• 英文别名: 13-O-tert-butyl 1-O-methyl (E)-8,11-dioxotridec-2-enedioate
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: HLWQVFFIORKXNK-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙二酸单叔丁酯 在 Grubbs catalyst first generation 二丁基镁 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 为溶剂， 反应 33.25h， 生成 (E)-8,11-dioxotridec-2-enedioic acid 13-tert-butyl ester 1-methyl ester
  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

• The Scope of Catalytic Enantioselective Tandem Carbonyl Ylide Formation−Intramolecular [3 + 2] Cycloadditions
  作者：David M. Hodgson、Agnès H. Labande、Françoise Y. T. M. Pierard、María Á. Expósito Castro

  DOI：10.1021/jo0343735

  日期：2003.8.1

  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.