4-oxo-9-decenoic acid | 529508-00-7

• 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: 4-oxo-9-decenoic acid
• 英文别名: 4-Oxodec-9-enoic acid；4-oxodec-9-enoic acid
• CAS: 529508-00-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: FTPWJGVRXGRCNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46 °C
• 沸点：
  347.1±25.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-oxo-9-decenoic acid 在 二丁基镁 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 20.5h， 生成 tert-butyl 3,6-dioxododec-11-enoate
  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：

  5-己-5-烯基-2,3-二氢呋喃 在 jones reagent 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以10.4 g的产率得到4-oxo-9-decenoic acid
  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

• A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction
  作者：Varinder Aggarwal、Jonathan Killen、John Leonard

  DOI：10.1055/s-0029-1219210

  日期：2010.3

  A Morita-Baylis-Hillman-type reaction has been applied to the asymmetric preparation of azaspirocycles in high yield and diastereoselectivity. The optimisation of the reaction is discussed and a model for the origin of diastereoselectivity is proposed.

  森田-贝利斯-希尔曼型反应已被应用于高效和高立体选择性地不对称合成氮杂螺环化合物。本文探讨了该反应的优化方法，并提出了一种解释立体选择性起源的模型。
• 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：——
• 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.