(S)-1-phenyl-1-eicosanol | 1271732-60-5

• 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: (S)-1-phenyl-1-eicosanol
• 英文别名: (1S)-1-phenylicosan-1-ol
• CAS: 1271732-60-5
• 化学式: C₂₆H₄₆O
• 分子量: 374.651
• InChiKey: OPDCMCRZKBEGDC-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  eicosanophenone 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 、 盐酸 作用下， 以 四氢呋喃 、 甲苯 、 水 为溶剂， 反应 1.67h， 以70%的产率得到(S)-1-phenyl-1-eicosanol
  参考文献：
  名称：

  Asymmetric synthesis of new chiral long chain alcohols

  摘要：

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.010

文献信息

• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.