1-Acetoxy-2,3,3-trimethylbutan | 102439-06-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Acetoxy-2,3,3-trimethylbutan
• 英文别名: 2,3,3-Trimethyl-butylacetat；acetic acid-(2,3,3-trimethyl-butyl ester)；Essigsaeure-(2,3,3-trimethyl-butylester)；2,3,3-Trimethylbutyl ethanoate；2,3,3-trimethylbutyl acetate
• CAS: 102439-06-5
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: XGQAAEGIHGLFGO-UHFFFAOYSA-N

物化性质

• 沸点：
  153.5±8.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Acetoxy-2,3,3-trimethylbutan 在 Pseudomonas cepacia lipase 作用下， 以 aq. phosphate buffer 、 异丙醇 为溶剂， 生成 (+)(S)-2,3,3-trimethyl-1-butanol
  参考文献：
  名称：

  A new mechanism of enantioselectivity toward chiral primary alcohol by lipase from Pseudomonas cepacia

  摘要：

  The stereo-recognition of chiral primary alcohols by lipase from Pseudomonas cepacia was found to deviate from earlier observations. Enantioselectivity toward 14 pairs of chiral primary alcohol esters by this lipase was dependent on the existence of an Onon-alpha (oxygen at non-alpha-position of the acyloxy group) in the alcohol moiety, and decreased as the size of the acyl moiety increased. Chemical modification on the lipase and molecular dynamics simulations indicated that Tyr(29) located within the catalytic cavity forms a hydrogen bond with the Onon-alpha of the preferred enantiomer of the primary alcohol ester. However, a larger acyl moiety suffered stronger hindrance from the catalytic cavity wall of the lipase, pushing the Onon-alpha away from Tyr(29), and thus weakening the stereo-recognition. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.08.014
• 作为产物：
  描述：

  3-bromo-4,4-dimethylpentan-2-one 在 lithium aluminium tetrahydride 、 乙醚 、 硫酸 作用下， 生成 1-Acetoxy-2,3,3-trimethylbutan
  参考文献：
  名称：

  The Synthesis of Branched Primary and Secondary Alkyl Acetates

  摘要：

  DOI：

  10.1021/ja01601a068

文献信息

• The Synthesis of Branched Primary and Secondary Alkyl Acetates
  作者：Shalom Sarel、Melvin S. Newman

  DOI：10.1021/ja01601a068

  日期：1956.10
• A new mechanism of enantioselectivity toward chiral primary alcohol by lipase from Pseudomonas cepacia
  作者：Xiao Meng、Li Guo、Gang Xu、Jian-Ping Wu、Li-Rong Yang

  DOI：10.1016/j.molcatb.2014.08.014

  日期：2014.11

  The stereo-recognition of chiral primary alcohols by lipase from Pseudomonas cepacia was found to deviate from earlier observations. Enantioselectivity toward 14 pairs of chiral primary alcohol esters by this lipase was dependent on the existence of an Onon-alpha (oxygen at non-alpha-position of the acyloxy group) in the alcohol moiety, and decreased as the size of the acyl moiety increased. Chemical modification on the lipase and molecular dynamics simulations indicated that Tyr(29) located within the catalytic cavity forms a hydrogen bond with the Onon-alpha of the preferred enantiomer of the primary alcohol ester. However, a larger acyl moiety suffered stronger hindrance from the catalytic cavity wall of the lipase, pushing the Onon-alpha away from Tyr(29), and thus weakening the stereo-recognition. (C) 2014 Elsevier B.V. All rights reserved.