(S)-1-phenyl-1-dodecanol | 270076-41-0

• 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-dodecanol
• 英文别名: (1S)-1-phenyldodecan-1-ol
• CAS: 270076-41-0
• 化学式: C₁₈H₃₀O
• 分子量: 262.436
• InChiKey: DTXGFKMOQIMZIS-SFHVURJKSA-N

物化性质

• 熔点：
  34.4-35.2 °C
• 沸点：
  336.4±10.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  月桂基苯甲酮 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95%的产率得到(S)-1-phenyl-1-dodecanol
  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

• Expanding substrate scope of lipase-catalyzed transesterification by the utilization of liquid carbon dioxide
  作者：Hai Nam Hoang、Tomoko Matsuda

  DOI：10.1016/j.tet.2015.11.052

  日期：2016.11

  Secondary alcohols having bulky substituents on both sides of the chiral center are often poor substrates for most lipases. Here we reported that substrate scopes of two of the most used lipases, Candida antarctica lipase B and Burkholderia cepacia lipase, were found to be expanded toward more bulky secondary alcohols such as 1-phenyl-1-dodecanol and 2-methyl-1-phenyl-1-propanol by simply using them in liquid carbon dioxide as a solvent. The effects of solvents, reaction pressure, and pre-treatment of the enzyme with liquid CO2 on this acceleration phenomenon were also studied. (C) 2015 Elsevier Ltd. All rights reserved.
• Iron Achieves Noble Metal Reactivity and Selectivity: Highly Reactive and Enantioselective Iron Complexes as Catalysts in the Hydrosilylation of Ketones
  作者：Tim Bleith、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/ja512986m

  日期：2015.2.25

  Chiral iron alkyl and iron alkoxide complexes bearing boxmi pincers as stereodirecting ligands have been employed as catalysts for enantioselective hydrosilylation reactions with unprecedented activity and selectivity (TOF = 240 h(-1) at -40 degrees C, ee up to 99% for alkyl aryl ketones), which match the performance of previously established noble-metal-based catalysts. This shows the potential of earth-abundant metals such as iron for replacing platinum-metals without any drawbacks for the reaction design.
• PROCESS FOR THE PREPARATION OF ALKOXYLATES COMPOSITIONS
  申请人：Rhodia Operations

  公开号：EP3717447A1

  公开（公告）日：2020-10-07
• 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.