(R)-1-(naphthalen-1-yl)ethyl octanoate | 1369869-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-1-(naphthalen-1-yl)ethyl octanoate
• CAS: 1369869-20-4
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: OBXBZCBBNBFPDZ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  辛酸乙烯酯 、 1-(1-萘)乙醇 在 lipase B from Candida antarctica 作用下， 以 环己烷 为溶剂， 反应 1.75h， 以90%的产率得到(R)-1-(naphthalen-1-yl)ethyl octanoate
  参考文献：
  名称：

  Catalytic performance of H-β nanozeolite microspheres in one-pot dynamic kinetic resolution of aromatic sec-alcohols

  摘要：

  In this paper, uniform H-beta nanozeolite microsphere (beta-ZMS) prepared by polymerization-induced colloid aggregation, combined with an immobilized lipase B from Candida antarctica (commercially available Novozym (R) 435), is applied as a racemization catalyst to the one-pot dynamic kinetic resolution (DKR) of aromatic sec-alcohols. The DKRs of various aromatic sec-alcohols can be carried out with high selectivity and conversion under optimum conditions. Importantly, it is found that, compared to commercial zeolites beta (C-beta), beta-ZMSs display high selectivity for small sec-alcohol molecules because their shorter microporous channels reduce the diffusion time of substrate/product in the three-dimensional framework, and thereby decrease the possibility of secondary reactions. However, the beta-ZMS5 show a high racemization rate in the DKR of large sec-alcohol molecules, such as racemic 1-(1-naphthyl)-ethanol, thanks to their abundant accessible active sites. This observation will not only benefit the performance of acidic zeolite catalysts in one-pot DKR systems but also provide a new perspective on the application of nanozeolites in catalysis. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2011.12.021