(2S,3S)-2,3,4,4-Tetramethyl-pentanoic acid ethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-2,3,4,4-Tetramethyl-pentanoic acid ethyl ester
• 英文别名: ethyl (2S,3S)-2,3,4,4-tetramethylpentanoate
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: BEROKFFIYJACEF-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4,4-三甲基戊酸 在 N-甲基吗啉 、 硫酸 、 cesium fluoride 、 copper dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2,3,4,4-Tetramethyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective radical-radical disproportionation

  摘要：

  Radicals a to the carbonyl of ethyl 3,4,4-trimethylpentanoate couple with little stereoselectivity while analogous tertiary radicals derived from ethyl 2,3,4,4-tetramethylpentanoate disproportionate at 25 degrees C to give the corresponding alkene and alkane. The alkane is formed by disproportionation with a diastereoselectivity of greater than 20:1.

  DOI：

  10.1016/s0040-4039(00)61496-x

文献信息

• Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates
  作者：David J. Hart、Ramanarayanan Krishnamurthy

  DOI：10.1021/jo00042a029

  日期：1992.7

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.
• Stereoselective radical-radical disproportionation
  作者：Ned A. Porter、Ian J. Rosenstein

  DOI：10.1016/s0040-4039(00)61496-x

  日期：1993.12

  Radicals a to the carbonyl of ethyl 3,4,4-trimethylpentanoate couple with little stereoselectivity while analogous tertiary radicals derived from ethyl 2,3,4,4-tetramethylpentanoate disproportionate at 25 degrees C to give the corresponding alkene and alkane. The alkane is formed by disproportionation with a diastereoselectivity of greater than 20:1.