-(methyl 2-methyl-3-hydroxyheptanoate) | 127464-85-1

• 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 2-methyl-3-hydroxyheptanoate)
• 英文别名: methyl (2R,3R)-3-hydroxy-2-methylheptanoate
• CAS: 127464-85-1
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: DOMUKTSMUVTFHD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-methyl-3-oxoheptanoate 在 氢氧化钾 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 -(methyl 2-methyl-3-hydroxyheptanoate)
  参考文献：
  名称：

  Watabu, Hisashi; Ohkubo, Munemasa; Matsubara, Hiroshi, Chemistry Letters, 1989, p. 2183 - 2184

  摘要：

  DOI：

文献信息

• 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.
• Watabu, Hisashi; Ohkubo, Munemasa; Matsubara, Hiroshi, Chemistry Letters, 1989, p. 2183 - 2184
  作者：Watabu, Hisashi、Ohkubo, Munemasa、Matsubara, Hiroshi、Sakai, Takashi、Tsuboi, Sadao、Utaka, Masanori

  DOI：——

  日期：——