1'-(2'',4'',6''-triisopropylphenyl)ethyl acetoxyacetate | 1400563-23-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1'-(2'',4'',6''-triisopropylphenyl)ethyl acetoxyacetate
• CAS: 1400563-23-6
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: DZUVVFYFQNRWJN-UHFFFAOYSA-N

物化性质

• 沸点：
  395.4±37.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1'-(2'',4'',6''-triisopropylphenyl)ethyl acetoxyacetate 在 Candida antarctica lipase B 作用下， 以 环戊醇 为溶剂， 反应 31.0h， 以81%的产率得到1'-(2'',4'',6''-triisopropylphenyl)ethyl hydroxyacetate
  参考文献：
  名称：

  Examination of spacer effects on stereochemical recognition of a remote sterically hindered chiral center in lipase-catalyzed acylation

  摘要：

  To date, the enzyme-catalyzed kinetic resolution of the secondary alcohol [Ar-C*H(CH3)OH, Ar = 2,4,6'-triisopropylphenyl] has not been available, due to high steric hindrance around the hydroxy group. To achieve resolution, the reaction site was extended by the introduction of two kinds of spacers, [-C(=O)CH2-] and [-C(=O)C**HCN-]. In the first substrate, the recognition of remote chirality [Ar-C*H(CH3)O-C(=O)CH2-OH] by acylation with Burkholderia cepacia lipase was examined by changing reaction conditions and acyl donors. An E = 22 in the preference of (1'R)-isomer, was recorded with vinyl acetate as an acyl donor at 25 degrees C. In the second substrate, there was a matched enantiomeric pair [stereoselective ratio at C-1' = 15, in the preference of (1'R)-isomer] and a mismatched pair [stereoselective ratio at C-1' = 2.5, in the preference of (1'S)-isomer] based on the relative stereochemistry between the two chiral centers [Ar-C*H(CH3)O-C(=O)C**HCN-OH]. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.05.006
• 作为产物：
  描述：

  1-(2,4,6-triisopropylphenyl)ethanol 、 乙酰氧基乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 以60%的产率得到1'-(2'',4'',6''-triisopropylphenyl)ethyl acetoxyacetate
  参考文献：
  名称：

  Examination of spacer effects on stereochemical recognition of a remote sterically hindered chiral center in lipase-catalyzed acylation

  摘要：

  To date, the enzyme-catalyzed kinetic resolution of the secondary alcohol [Ar-C*H(CH3)OH, Ar = 2,4,6'-triisopropylphenyl] has not been available, due to high steric hindrance around the hydroxy group. To achieve resolution, the reaction site was extended by the introduction of two kinds of spacers, [-C(=O)CH2-] and [-C(=O)C**HCN-]. In the first substrate, the recognition of remote chirality [Ar-C*H(CH3)O-C(=O)CH2-OH] by acylation with Burkholderia cepacia lipase was examined by changing reaction conditions and acyl donors. An E = 22 in the preference of (1'R)-isomer, was recorded with vinyl acetate as an acyl donor at 25 degrees C. In the second substrate, there was a matched enantiomeric pair [stereoselective ratio at C-1' = 15, in the preference of (1'R)-isomer] and a mismatched pair [stereoselective ratio at C-1' = 2.5, in the preference of (1'S)-isomer] based on the relative stereochemistry between the two chiral centers [Ar-C*H(CH3)O-C(=O)C**HCN-OH]. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.05.006