1'-(2'',4'',6''-triisopropylphenyl)ethyl hydroxyacetate | 1400563-20-3

• 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 hydroxyacetate
• 英文别名: 1-[2,4,6-Tri(propan-2-yl)phenyl]ethyl 2-hydroxyacetate；1-[2,4,6-tri(propan-2-yl)phenyl]ethyl 2-hydroxyacetate
• CAS: 1400563-20-3
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: NPLMAZLGRQUKHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1'-(2'',4'',6''-triisopropylphenyl)ethyl hydroxyacetate 在 三氧化硫吡啶 、 三乙胺 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 1'-(2'',4'',6''-triisopropylphenyl)ethyl 2-cyano-2-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)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