1-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethanol | 469874-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethanol
• 英文别名: (1S)-2-(3,4-dihydro-1H-isoquinolin-2-yl)-1-phenylethanol
• CAS: 469874-45-1
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: ZOLSBNMKZYHYDL-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethanol 在 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 反应 20.5h， 生成 (1S)-2-(3,4-dihydro-1H-isoquinolin-2-yl)-N-methyl-1-phenylethanamine
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 1-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethanol
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9

文献信息

• Acid-Assisted Ru-Catalyzed Enantioselective Amination of 1,2-Diols through Borrowing Hydrogen
  作者：Li-Cheng Yang、Ya-Nong Wang、Yao Zhang、Yu Zhao

  DOI：10.1021/acscatal.6b02959

  日期：2017.1.6

  Here, we present a highly enantioselective synthesis of 1,2-amino alcohols from readily available racemic 1,2-diols through a borrowing hydrogen process. An intriguing acid effect was discovered for this Ru-catalyzed amination reaction, which led to a significant improvement of the stereoselectivity of the process. Preliminary mechanistic studies suggest a scenario of Brønsted acid-assisted dynamic

  在这里，我们介绍了通过借用氢过程从容易获得的外消旋1,2-二醇中高度对映选择性合成1,2-氨基醇的方法。对于这种Ru催化的胺化反应，发现了一种引人入胜的酸效应，这导致了该方法的立体选择性的显着改善。初步的机理研究表明，布朗斯台德酸辅助的醇动力学动力学不对称胺化的情况。
• Ruthenium-Catalyzed Enantioselective Synthesis of β-Amino Alcohols from 1,2-Diols by “Borrowing Hydrogen”
  作者：Anggi Eka Putra、Yohei Oe、Tetsuo Ohta

  DOI：10.1002/ejoc.201300692

  日期：2013.9

  Enantioselective synthesis of β-amino alcohols from 1,2-diols by the use of [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS catalysis was developed. Several 1,2-diols were treated with secondary amines to afford the corresponding optically active β-amino alcohols in up to 99 % yield with 77 % ee.

  开发了使用 [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS 催化从 1,2-二醇对映选择性合成 β-氨基醇。几种 1,2-二醇用仲胺处理，得到相应的光学活性 β-氨基醇，产率高达 99%，ee 为 77%。