methyl 3-hydroxy-2-methylheptanoate | 77877-27-1

• 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 3-hydroxy-2-methylheptanoate
• 英文别名: rac-(2R,3S)-methyl 3-hydroxy-2-methylheptanoate；methyl (2S,3R)-3-hydroxy-2-methylheptanoate
• CAS: 77877-27-1
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: DOMUKTSMUVTFHD-JGVFFNPUSA-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：

  (+/-)-methyl 3-hydroxy-2-methyleneheptanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 -(methyl 2-methyl-3-hydroxyheptanoate) 、 methyl 3-hydroxy-2-methylheptanoate
  参考文献：
  名称：

  Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis–Hillman adducts. Total synthesis of (±)-sitophilate

  摘要：

  We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00647-0

文献信息

• Regioselective Carbonylation of <i>trans</i>-Disubstituted Epoxides to β-Lactones: A Viable Entry into <i>syn</i>-Aldol-Type Products
  作者：Michael Mulzer、Bryan T. Whiting、Geoffrey W. Coates

  DOI：10.1021/ja405151n

  日期：2013.7.31

  reported for the regioselective carbonylation of trans-disubstituted epoxides to cis-β-lactones. The two catalysts display high and opposing selectivities, which generally are difficult to achieve for this class of epoxides. The resulting β-lactones are well-defined precursors for a wide variety of aldol-type compounds. Altogether, carbonylation of disubstituted epoxides is established as a viable and

  据报道，两种新催化剂可用于将反式双取代环氧化物区域选择性羰基化成顺式-β-内酯。这两种催化剂显示出高且相反的选择性，这对于此类环氧化物通常难以实现。由此产生的 β-内酯是各种羟醛型化合物的明确前体。总之，双取代环氧化物的羰基化被确立为合成和抗羟醛产品的可行且经济的入口。
• 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
• 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：——