-(methyl 2-methyl-3-hydroxyheptanoate) | 77877-28-2

• 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: (2R,3S)-methyl 3-hydroxy-2-methylheptanoate；methyl (2R,3S)-3-hydroxy-2-methylheptanoate
• CAS: 77877-28-2
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: DOMUKTSMUVTFHD-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (2S,3RS,4aS,5R,8S,8aR)-2-butyl-3,5,10,10-tetramethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 2.5h， 生成 -(methyl 2-methyl-3-hydroxyheptanoate)
  参考文献：
  名称：

  [2+3] CycloadditionsBetween Nitroalkenes and Camphor-Derived OxazolineN-Oxidesand Radical Denitration of the Adducts

  摘要：

  樟脑衍生的噁唑啉 N-氧化物 2 与硝基烯 3a-f 发生[2+3] 环加成反应，生成立体选择性加合物 4a-f。自由基脱氮后进行酸性水解，可得到反醛 8a,b。自由基中间体也会被合适的烯烃捕获，从而产生单一的立体异构体。

  DOI：

  10.1055/s-2003-40191

文献信息

• Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates
  作者：D. A. Evans、J. Bartroli、T. L. Shih

  DOI：10.1021/ja00398a058

  日期：1981.4
• 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.
• EVANS D. A.; BARTROLI J.; SHIH T. L., J. AMER. CHEM. SOC., 1981, 103 NO 8, 2127-2129
  作者：EVANS D. A.、 BARTROLI J.、 SHIH T. L.

  DOI：——

  日期：——