(2-methylethyl) (R)-5-hydroxy-3-oxooctanoate

• 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) (R)-5-hydroxy-3-oxooctanoate
• 英文别名: (R)-isopropyl 5-hydroxy-3-oxooctanoate；isopropyl 5-hydroxy-3-oxo-octanoate；propan-2-yl (5R)-5-hydroxy-3-oxooctanoate
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: LNTXNMSXTPTZTK-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  正丁醛 、 双乙烯酮 、 异丙醇 以84%的产率得到
  参考文献：
  名称：

  Masahiko Hayashi, Tetsuya Inoue, Yasunori Miyamoto, Nobuki Oguni, Tetrahedron, 50 (1994) N 15, S 4385-4398

  摘要：

  DOI：

文献信息

• Asymmetric carboncarbon bond forming reactions catalyzed by chiral Schiff base—titanium alkoxide complexes
  作者：Masahiko Hayashi、Tetsuya Inoue、Yasunori Miyamoto、Nobuki Oguni

  DOI：10.1016/s0040-4020(01)89374-1

  日期：1994.4

  The enantioselective addition of trimethylsilyl cyanide to a variety of aldehydes proceeded by the aid of a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases and gave the corresponding cyanohydrins in high optical yield (up to 96% e.e.). A remarkable rate enhancement was brought about by the addition of the Schiff base to the titanium alkoxide mediated

  在由四异丙醇钛[Ti（O- i- Pr）4 ]和手性席夫碱原位制备的催化剂的帮助下，将三甲基甲硅烷基氰化物对映选择性加成到各种醛中，从而以高光学收率得到了相应的氰醇（最多到96％ee）。通过将席夫碱加入到钛醇盐介导的醛的甲硅烷基氰化中，可以显着提高速率。该催化剂体系还促进了双烯酮与醛的高度对映选择性反应，这导致形成光学活性的5-羟基-3-氧代酯。
• Novel enantioselective reaction of diketene with aldehydes promoted by chiral Schiff base–titanium alkoxide complex
  作者：Masahiko Hayashi、Tetsuya Inoue、Nobuki Oguni

  DOI：10.1039/c39940000341

  日期：——

  Reaction of a variety of aldehydes with diketene in the presence of chiral Schiff base–titanium alkoxide complexes proceeds with high enantioselectivity to afford the corresponding 5-hydroxy-3-oxoesters.

  在手性席夫碱钛氧化物络合物存在下，各种醛与二乙烯的反应具有很高的对映选择性，可以得到相应的 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.