tert-butyl (2R)-2-[(1R)-3-oxocyclohexyl]propanoate | 1432602-23-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2R)-2-[(1R)-3-oxocyclohexyl]propanoate
• CAS: 1432602-23-7
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: MJXFHCYUXHIQKU-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-[(1R)-3-oxocyclohexyl]propanoate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (2R)-2-[(7R)-1,4-dioxaspiro[4.5]decan-7-yl]propan-1-ol
  参考文献：
  名称：

  Catalytic Enantioselective Carbon Insertion into the β-Vinyl C–H Bond of Cyclic Enones

  摘要：

  Chiral oxazaborolidinium ion-catalyzed C-sp(2)-H functionalization of enones using diazoacetate has been developed. Various beta-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.

  DOI：

  10.1021/ja402873b
• 作为产物：
  描述：

  2-甲基-3-氧代丁酸叔丁酯 在 [RhCl2(PPh3)3] 、 (3aS)-3,3-bis(3,5-dimethylphenyl)-1-naphthalen-1-yl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole 、 4-乙酰氨基苯磺酰叠氮 、 氢气 、 双三氟甲烷磺酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， -20.0~20.0 ℃ 、3.0 MPa 条件下， 反应 60.17h， 生成 tert-butyl (2R)-2-[(1R)-3-oxocyclohexyl]propanoate 、 tert-butyl (R)-2-((S)-3-oxocyclohexyl)propanoate
  参考文献：
  名称：

  Catalytic Enantioselective Carbon Insertion into the β-Vinyl C–H Bond of Cyclic Enones

  摘要：

  Chiral oxazaborolidinium ion-catalyzed C-sp(2)-H functionalization of enones using diazoacetate has been developed. Various beta-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.

  DOI：

  10.1021/ja402873b

文献信息

• Catalytic Enantioselective Carbon Insertion into the β-Vinyl C–H Bond of Cyclic Enones
  作者：Sung Il Lee、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1021/ja402873b

  日期：2013.5.15

  Chiral oxazaborolidinium ion-catalyzed C-sp(2)-H functionalization of enones using diazoacetate has been developed. Various beta-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.