(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.
• Complete reversal of enantioselection using oxazoline-containing Schiff base ligands derived from l-serine in enantioselective addition of diketene to aldehydes
  作者：Changhu Chu、Koji Morishita、Takanori Tanaka、Masahiko Hayashi

  DOI：10.1016/j.tetasy.2006.09.026

  日期：2006.10

  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.
• Enantioselective addition Of diketene to aldehydes promoted by chiral schiff base—titanium alkoxide complex. Application to asymmetric synthesis of potential inhibitors of HMG coenzyme reductase
  作者：Masahiko Hayashi、Kazuya Yoshimoto、Naohito Hirata、Kiyoshi Tanaka、Nobuki Oguni、Katsumasa Harada、Akio Matsushita、Yasuhiro Kawachi、Hiroshi Sasaki

  DOI：10.1560/px53-y9jj-fu8v-gken

  日期：2001.12

  Highly enantioselective addition of diketene to aldehydes was achieved by using novel Schiff base—titanium alkoxide complexes. Up to 92% ee of 5-hydroxy-3-oxoesters was obtained. This procedure provides an efficient method for the asymmetric synthesis of potential inhibitors of HMG coenzyme reductase.

  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。