ethyl (5E)-3-hydroxyoct-5-enoate | 71677-19-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (5E)-3-hydroxyoct-5-enoate
• 英文别名: ethyl (E)-3-hydroxyoct-5-enoate
• CAS: 71677-19-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: UIWVSNIRNXLEKC-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (5E)-3-hydroxyoct-5-enoate 在 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (7E)-3-oxo-5-(1,1,2,2-tetramethyl-1-silapropoxy)dec-7-enenitrile
  参考文献：
  名称：

  Unsaturated Oxo−Nitriles:  Stereoselective, Chelation-Controlled Conjugate Additions

  摘要：

  Addition of Grignard reagents to the unsaturated oxo-nitrile 10 (4-hydroxy-4-methyl-6-oxocyclohex-1-enecarbonitrile) provides conjugate addition products with virtually complete stereocontrol. Mechanistic evidence supports a chelation-controlled conjugate addition via alkylmagnesium alkoxide inter mediates. Diverse Grignard reagents having sp(3)-, sp(2)-, and sp-hybridized carbons react with comparable efficiency, with even sterically demanding nucleophiles adding with complete stereocontrol. Unsaturated oxo-nitriles that are incapable of chelation afford diastereomeric conjugate addition products through an unusual boatlike transition state. Collectively, these reactions illustrate the complementary stereoselectivity of chelation-controlled conjugate additions to hydroxylated, unsaturated oxo-nitriles and stereoelectronically controlled conjugate additions to enones.

  DOI：

  10.1021/jo9909709
• 作为产物：
  描述：

  ethyl (5E)-3-oxooct-5-enoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以88%的产率得到ethyl (5E)-3-hydroxyoct-5-enoate
  参考文献：
  名称：

  Unsaturated Oxo−Nitriles:  Stereoselective, Chelation-Controlled Conjugate Additions

  摘要：

  Addition of Grignard reagents to the unsaturated oxo-nitrile 10 (4-hydroxy-4-methyl-6-oxocyclohex-1-enecarbonitrile) provides conjugate addition products with virtually complete stereocontrol. Mechanistic evidence supports a chelation-controlled conjugate addition via alkylmagnesium alkoxide inter mediates. Diverse Grignard reagents having sp(3)-, sp(2)-, and sp-hybridized carbons react with comparable efficiency, with even sterically demanding nucleophiles adding with complete stereocontrol. Unsaturated oxo-nitriles that are incapable of chelation afford diastereomeric conjugate addition products through an unusual boatlike transition state. Collectively, these reactions illustrate the complementary stereoselectivity of chelation-controlled conjugate additions to hydroxylated, unsaturated oxo-nitriles and stereoelectronically controlled conjugate additions to enones.

  DOI：

  10.1021/jo9909709

文献信息

• JPS55136249A
  申请人：——

  公开号：JPS55136249A

  公开（公告）日：1980-10-23
• Unsaturated Oxo−Nitriles:  Stereoselective, Chelation-Controlled Conjugate Additions
  作者：Fraser F. Fleming、Jianping Guo、Qunzhao Wang、Douglas Weaver

  DOI：10.1021/jo9909709

  日期：1999.11.1

  Addition of Grignard reagents to the unsaturated oxo-nitrile 10 (4-hydroxy-4-methyl-6-oxocyclohex-1-enecarbonitrile) provides conjugate addition products with virtually complete stereocontrol. Mechanistic evidence supports a chelation-controlled conjugate addition via alkylmagnesium alkoxide inter mediates. Diverse Grignard reagents having sp(3)-, sp(2)-, and sp-hybridized carbons react with comparable efficiency, with even sterically demanding nucleophiles adding with complete stereocontrol. Unsaturated oxo-nitriles that are incapable of chelation afford diastereomeric conjugate addition products through an unusual boatlike transition state. Collectively, these reactions illustrate the complementary stereoselectivity of chelation-controlled conjugate additions to hydroxylated, unsaturated oxo-nitriles and stereoelectronically controlled conjugate additions to enones.