4-tert-butyl 1-((1S,2R)-2-phenylcyclohexyl) 2-((tert-butyldimethylsilyl)oxy)-2-((E)-1,5-di(furan-2-yl)-3-oxopent-4-en-1-yl)succinate | 1366465-26-0

• 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: 4-tert-butyl 1-((1S,2R)-2-phenylcyclohexyl) 2-((tert-butyldimethylsilyl)oxy)-2-((E)-1,5-di(furan-2-yl)-3-oxopent-4-en-1-yl)succinate
• 英文别名: 4-O-tert-butyl 1-O-[(1S,2R)-2-phenylcyclohexyl] (2R)-2-[(E,1S)-1,5-bis(furan-2-yl)-3-oxopent-4-enyl]-2-[tert-butyl(dimethyl)silyl]oxybutanedioate
• CAS: 1366465-26-0
• 化学式: C₃₉H₅₂O₈Si
• 分子量: 676.923
• InChiKey: TYOZUQZSWJIJOD-WAFGKGFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  醋酸叔丁酯 、 (1S,2R)-2-phenylcyclohexyl tert-butyldimethylsilyl glyoxylate 、 (E,E)-1,5-di-(2-furyl)pent-1,4-dien-3-one 在 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以80%的产率得到4-tert-butyl 1-((1S,2R)-2-phenylcyclohexyl) 2-((tert-butyldimethylsilyl)oxy)-2-((E)-1,5-di(furan-2-yl)-3-oxopent-4-en-1-yl)succinate
  参考文献：
  名称：

  Three-Component Glycolate Michael Reactions of Enolates, Silyl Glyoxylates, and α,β-Enones

  摘要：

  Silyl glyoxylates react with enolates and enones to afford either glycolate aldol or Michael adducts. Product identity is controlled by the countercation associated with the enolate. Reformatsky nucleophiles in the presence of additional Zn(OTf)(2) result in aldol coupling (A), while lithium enolates provide the Michael coupling (B). Deprotonation of the aldol product A with LDA induces equilibration to form the minor diastereomer of Michael product B. This observation suggests that formation of the major diastereomer of Michael product B does not occur via an aldol/retro-aldol/Michael sequence.

  DOI：

  10.1021/jo202679u

文献信息

• Three-Component Glycolate Michael Reactions of Enolates, Silyl Glyoxylates, and α,β-Enones
  作者：Daniel C. Schmitt、Ericka J. Malow、Jeffrey S. Johnson

  DOI：10.1021/jo202679u

  日期：2012.4.6

  Silyl glyoxylates react with enolates and enones to afford either glycolate aldol or Michael adducts. Product identity is controlled by the countercation associated with the enolate. Reformatsky nucleophiles in the presence of additional Zn(OTf)(2) result in aldol coupling (A), while lithium enolates provide the Michael coupling (B). Deprotonation of the aldol product A with LDA induces equilibration to form the minor diastereomer of Michael product B. This observation suggests that formation of the major diastereomer of Michael product B does not occur via an aldol/retro-aldol/Michael sequence.