(S)-(E)-isopropyl 5-hydroxy-3-oxo-6-octenoate

• 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: (S)-(E)-isopropyl 5-hydroxy-3-oxo-6-octenoate
• 英文别名: (2-methylethyl) (S,E)-5-hydroxy-3-oxooct-6-enoate；propan-2-yl (E,5S)-5-hydroxy-3-oxooct-6-enoate
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: JFYGRLCBGRMTMW-XNPJLODASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  双乙烯酮 、 巴豆醛 、 异丙醇 在 titanium(IV) isopropylate 、 (S)-4-HOCH₂-5,5-di-Et-2-(2-HO-3,5-di-tBu-phenyl)-2-oxazoline 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 (S)-(E)-isopropyl 5-hydroxy-3-oxo-6-octenoate 、 (2-methylethyl) (R,E)-5-hydroxy-3-oxooct-6-enoate
  参考文献：
  名称：

  Complete reversal of enantioselection using oxazoline-containing Schiff base ligands derived from l-serine in enantioselective addition of diketene to aldehydes

  摘要：

  Starting from one stereogenic center (in this case from L-serine), we obtained two chiral Schiff bases possessing oxazoline moieties, each of which recognized a different enantioface of aldehydes with a high enantionteric excess [up to 93% ee (R) and 89% ee (S)] in the addition reaction of diketene to 2-furfural. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.026

文献信息

• The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 <i>Bis</i>-pyran Unit of Phorboxazole B
  作者：Paul A. Clarke、Soraia Santos、Nimesh Mistry、Laurence Burroughs、Alexander C. Humphries

  DOI：10.1021/ol102860r

  日期：2011.2.18

  The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.