methyl 3-hydroxy-2,4-dimethylpentanoate | 78655-80-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 3-hydroxy-2,4-dimethylpentanoate
• 英文别名: -2,4-dimethyl-3-hydroxypentanoic acid methyl ester；(-)-threo-methyl 2,4-dimethyl-3-hydroxypentanate；methyl (2R,3R)-3-hydroxy-2,4-dimethylpentanoate
• CAS: 78655-80-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: MXWOUIHOPZWBDL-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 methyl 3-hydroxy-2,4-dimethylpentanoate 在 吡啶 作用下， 生成 (2R,3R)-2,4-Dimethyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-pentanoic acid methyl ester
  参考文献：
  名称：

  A new protocol for the diastereoselective formation of lactones from either achiral or chiral vinylogous urethanes

  摘要：

  DOI：

  10.1021/jo00380a050
• 作为产物：
  描述：

  2,4-二甲基-3-羰基-戊酸甲酯 以62%的产率得到
  参考文献：
  名称：

  ITO, YOSHIO;KATSUKI, TSUTOMU;YAMAGUCHI, MASARU, TETRAHEDRON LETT., 1985, 26, N 38, 4643-4646

  摘要：

  DOI：

文献信息

• Stereoselectivity in the aldol reaction
  作者：A.I. Meyers、Yukio Yamamoto

  DOI：10.1016/0040-4020(84)80014-9

  日期：1984.1

  Chiral oxazolines, as their boron enolates derived from various boron triflates, react with aldehydes to give erythro-selectivity (97% + %) with enantiomeric purities of 50–60%. Achiral oxazolines as their boron enolates derived from diisopinocampheylborane give, on reaction with aldehydes, β-hydroxy esters with high threo-selectivity (90+%) in 77–85% ee. A variety of structurally different oxazolines

  手性恶唑啉是源自三氟甲磺酸三氟硼烷的硼烯酸酯，它与醛反应生成对映异构体纯度为50-60％的赤型选择性（97％+％）。非手性恶唑啉作为二异硫代樟脑硼烷的硼烯酸酯，与醛反应后，在77–85％ee中具有高苏式选择性（90％以上）的β-羟基酯。还研究了各种结构不同的恶唑啉，其中许多显示出高的赤型选择性。
• Enantioselective aldol reactions with high threo or erythro selectivity using boron azaenolates
  作者：A. I. Meyers、Yukio Yamamoto

  DOI：10.1021/ja00404a064

  日期：1981.7
• Enantioselective Capture and Retroracemization of (1-Bromoalkyl)boronic Esters by an N-Propanoyloxazolidinone Enolate and Iodide Ion
  作者：Donald S. Matteson、Hon-Wah Man

  DOI：10.1021/jo00098a036

  日期：1994.9

  Lithium enolates of N-propanoyloxazolidinones react with (1-bromoethyl)boronic esters to form predominantly threo-2-methyl-3-borylbutanoic acid derivatives. The reaction of enantiomerically pure oxazolidinone enolate 2 with excess racemic (1-bromoethyl)boronic ester rac-3a produced a single isolable product 4a in high diastereomeric and enantiomeric purity. Iodide catalysts resulted in racemization of any excess of ent-3a back to rac-3a so that both enantiomers were utilized via 3a (hence, ''retroracemization'') in the presence of 1 equiv of 2 to produce 4a, again in high purity and yield. The (1-bromoethyl)boronic ester rac-3b underwent similar retroracemization, though less efficiently. (Haloalkyl)boronic esters of much higher or lower reactivity did not undergo useful Im an attempt to direct the reaction to produce erythro isomer, 2 was paired with (1-bromoethyl)boronic ester 10, but the predominant product remained the threo isomer. The enantiomeric composition of this threo product was subsequently called into question by the observation that (1-bromopentyl)boronic ester 13 epimerizes readily to 14 and that both 13 and 14 with the lithium enolate of tert-butyl propanoate. This result contrasts sharply to the previously reported grossly differing behaviors of diastereomeric pairs of (1-chloroalkyl)boronic esters toward Grignard reagents and provides a warning that the previously reported reactions of (1-bromoalkyl)boronic esters with carboxylic ester enolates do not necessarily lead to good enantiomeric purities.
• Synthesis of Enantiomerically Pure Anti-Aldols:  A Highly Stereoselective Ester-Derived Titanium Enolate Aldol Reaction
  作者：Arun K. Ghosh、Masanobu Onishi

  DOI：10.1021/ja9539148

  日期：1996.1.1
• Copper(I)-Catalyzed Enantio- and Diastereoselective Tandem Reductive Aldol Reaction
  作者：Olivier Chuzel、Julia Deschamp、Christophe Chausteur、Olivier Riant

  DOI：10.1021/ol062398v

  日期：2006.12.1

  An efficient method for the enantioselective tandem reductive aldol reaction of methyl acrylate with aldehydes is reported. By using a copper( I) precursor and a proper diphosphane ligand, high reactivities can be reached, with TOF up to 40 000 h(-1). Taniaphos- based ligands lead to enantioselectivities of up to 97% in the case of the major syn diastereoisomer.