(2-methylethyl) (S)-5-hydroxy-3-oxo-5-phenylpentanoate | 210626-65-6

• 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: (2-methylethyl) (S)-5-hydroxy-3-oxo-5-phenylpentanoate
• 英文别名: (S)-isopropyl 5-hydroxy-5-phenyl-3-oxopentanoate；propan-2-yl (5S)-5-hydroxy-3-oxo-5-phenylpentanoate
• CAS: 210626-65-6
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: KZZKGALMOUVSQP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-methylethyl) (S)-5-hydroxy-3-oxo-5-phenylpentanoate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 生成 (S)-4-hydroxy-6-phenyl-5,6-dihydro-2-pyrone
  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
• 作为产物：
  描述：

  双乙烯酮 、 苯甲醛 、 异丙醇 在 titanium(IV) isopropylate 、 (S)-3,5-(t-Bu)2-2-HO-C₆H₂-C(1-naphthyl)=N-C(iPr)-CH₂OH 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 51.0h， 生成 (2-methylethyl) (R)-5-hydroxy-3-oxo-5-phenylpentanoate 、 (2-methylethyl) (S)-5-hydroxy-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  手性席夫碱-钛醇盐配合物促进的双烯酮对醛的对映选择性加成。应用于HMG辅酶还原酶的潜在抑制剂的不对称合成†

  摘要：

  通过使用新型的席夫碱-钛醇盐配合物，可以实现双烯酮向醛类的高度对映选择性加成。得到高达92％ee的5-羟基-3-氧代酯。该程序为HMG辅酶还原酶的潜在抑制剂的不对称合成提供了一种有效的方法。

  DOI：

  10.1560/px53-y9jj-fu8v-gken

文献信息

• Highly efficient preparation of optically active 5-hydroxy-3-oxoesters by enantioselective reaction of diketene with aldehydes promoted by novel chiral Schiff base-titanium alkoxide complexes
  作者：Masahiko Hayashi、Kiyoshi Tanaka、Nobuki Oguni

  DOI：10.1016/0957-4166(95)00230-m

  日期：1995.8

  Optically active 5-hydroxy-3-oxoesters 1 can be obtained in up to 91% enantiomeric excess (e.e.) by the enantioselective reaction of diketene with aldehydes promoted by novel chiral Schiff base-titanium alkoxide complexes.

  通过双烯酮与由新型手性席夫碱-钛醇盐配合物促进的醛的对映选择性反应，可以得到高达91％对映体过量（ee）的旋光5-羟基-3-氧酸酯1。
• Catalytic Enantioselective Reaction of Diketene with Aldehydes Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes
  作者：Nobuku Oguni、Kiyoshi Tanaka、Hajime Ishida

  DOI：10.1055/s-1998-1744

  日期：1998.6

  The catalytic enantioselective reaction of diketene with aldehydes was achieved by the use of a catalytic amount (20 mol%) of chiral Schiff base to afford the corresponding 5-hydroxy-3-oxoesters with high enantioselectivity.

  通过使用催化量（20 摩尔%）的手性席夫碱，实现了二乙烯与醛的催化对映体选择性反应，从而以高对映体选择性得到相应的 5-羟基-3-氧代酯。
• 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.