[(1R)-1-benzo[e][1,3]benzoxazol-2-yl-3-phenylpropyl] 3-phenylpropanoate | 1308372-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(1R)-1-benzo[e][1,3]benzoxazol-2-yl-3-phenylpropyl] 3-phenylpropanoate
• CAS: 1308372-96-4
• 化学式: C₂₉H₂₅NO₃
• 分子量: 435.522
• InChiKey: WLDNEUWUTRSJJI-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-Benzo[e][1,3]benzoxazol-2-yl-3-phenylpropan-1-ol 、 3-苯基丙酸 在 (+)-苯并四咪唑 、 三甲基乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1S)-1-benzo[e][1,3]benzoxazol-2-yl-3-phenylpropan-1-ol 、 、 [(1R)-1-benzo[e][1,3]benzoxazol-2-yl-3-phenylpropyl] 3-phenylpropanoate
  参考文献：
  名称：

  Kinetic Resolution of the Racemic 1-(Aryloxazol-2-yl)carbinols with Achiral Carboxylic Acids by Asymmetric Esterification: A New Method for the Preparation of Chiral 1,2-Amino Alcohols

  摘要：

  An efficient kinetic resolution of racemic 1-(aryloxazol-2-yl)carbinols with achiral carboxylic acids using pivalic anhydride in the presence of (R)-benzotetramisole ((R)-BTM) is reported. It was determined that the naphth[1,2-d]oxazole moiety at the C-1 position in the alcohols is a suitable structure to attain a high selectivity. An application to produce optically pure 1,2-amino alcohols was developed by the kinetic resolution of the racemic 1-(aryloxazol-2-yl)carbinols followed by a two-step cleavage of the aryloxazole part to form the corresponding amino group. Transition states that provide the desired (R)-esters from (R)-1-(benzoxazol-2-yl)ethan-1-ol or the undesired (S)-esters from (S)-1-(benzoxazol-2-yl)ethan-1-ol are disclosed by DFT calculations. Another transition state that affords the desired (R)-ester from (R)-1-(naphth[1,2-d]oxazol-2-yl)ethan-1-ol included in the racemic mixture is also estimated, and the structural features of these transition states are discussed.

  DOI：

  10.3987/com-10-s(e)120

文献信息

• Kinetic Resolution of the Racemic 1-(Aryloxazol-2-yl)carbinols with Achiral Carboxylic Acids by Asymmetric Esterification: A New Method for the Preparation of Chiral 1,2-Amino Alcohols
  作者：Isamu Shiina、Kenya Nakata、Keisuke Ono

  DOI：10.3987/com-10-s(e)120

  日期：——

  An efficient kinetic resolution of racemic 1-(aryloxazol-2-yl)carbinols with achiral carboxylic acids using pivalic anhydride in the presence of (R)-benzotetramisole ((R)-BTM) is reported. It was determined that the naphth[1,2-d]oxazole moiety at the C-1 position in the alcohols is a suitable structure to attain a high selectivity. An application to produce optically pure 1,2-amino alcohols was developed by the kinetic resolution of the racemic 1-(aryloxazol-2-yl)carbinols followed by a two-step cleavage of the aryloxazole part to form the corresponding amino group. Transition states that provide the desired (R)-esters from (R)-1-(benzoxazol-2-yl)ethan-1-ol or the undesired (S)-esters from (S)-1-(benzoxazol-2-yl)ethan-1-ol are disclosed by DFT calculations. Another transition state that affords the desired (R)-ester from (R)-1-(naphth[1,2-d]oxazol-2-yl)ethan-1-ol included in the racemic mixture is also estimated, and the structural features of these transition states are discussed.