1'-(2'',4'',6''-triisopropylphenyl)ethyl 2,2-dihydroxyacetate | 1400563-22-5

• 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: 1'-(2'',4'',6''-triisopropylphenyl)ethyl 2,2-dihydroxyacetate
• CAS: 1400563-22-5
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: MZGJKOMTGYYSOM-UHFFFAOYSA-N

物化性质

• 沸点：
  388.4±37.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1'-(2'',4'',6''-triisopropylphenyl)ethyl 2,2-dihydroxyacetate 在 甲醇 、 potassium carbonate 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-(-)-1-(2,4,6-三异丙基苯基)乙醇 、 (R)-(+)-1-(2,4,6-三异丙基苯基)乙醇
  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)ethyl acetoxyacetate 在 Candida antarctica lipase B 、 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 环戊醇 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 1'-(2'',4'',6''-triisopropylphenyl)ethyl 2,2-dihydroxyacetate
  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