3-(p-tolyl)butan-2-ol

• 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: 3-(p-tolyl)butan-2-ol
• 英文别名: 3-(4-Methylphenyl)butan-2-ol
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: BONMWTYWAIWNKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(p-tolyl)butan-2-ol 、 苯胺 在 (C₅(CH₃)5)Ir(NHCH(C₆H₅)CH(C₆H₅)NSO₂C₆(CH₃)5) 、 (Ra)-12-hydroxy-1,10-bis(2,4,6-triisopropylphenyl)-4,5,6,7-tetrahydrodiindeno[1,3,2]dioxaphosphocine 12-oxide 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以76%的产率得到N-((2S,3S)-3-p-tolylbutan-2-yl)aniline
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines

  摘要：

  The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, a-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

  DOI：

  10.1021/jacs.5b02212
• 作为产物：
  描述：

  1-methoxy-2-(p-tolyl)propene 在 氢溴酸 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 13.5h， 生成 3-(p-tolyl)butan-2-ol
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines

  摘要：

  The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, a-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

  DOI：

  10.1021/jacs.5b02212

文献信息

• Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol
  作者：Ming Huang、Xiuju Cai、Yan Liu、Zhuofeng Ke

  DOI：10.1016/j.cclet.2023.109323

  日期：2024.7

  Herein, we report the NHC-Ru catalyst system that realizes the chemo-selective transformation of ketones with methanol. By simply changing the base, a broad range of structurally diverse ketones, could be selectively and efficiently converted to the corresponding -methylated secondary alcohols or secondary alcohols. Remarkably, this catalytic system was very effective for the synthesis of bio-related

  在此，我们报道了NHC-Ru催化剂系统，该系统实现了酮与甲醇的化学选择性转化。通过简单地改变碱基，多种结构多样的酮可以选择性且有效地转化为相应的甲基化仲醇或仲醇。值得注意的是，该催化系统对于生物相关分子和氘代醇的合成以及甲基酮、伯醇和甲醇之间的三组分偶联非常有效。通过实验和DFT机理研究进一步揭示了反应机理。