(1R,2R,4R)-N-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine | 158411-96-2

• 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: (1R,2R,4R)-N-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine
• 英文别名: N-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine
• CAS: 158411-96-2
• 化学式: C₁₇H₂₅N
• 分子量: 243.392
• InChiKey: RDMPEKVKUMKCOW-INMHGKMJSA-N

物化性质

• 沸点：
  324.7±11.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  白樟油 在 三(五氟苯基)硼烷 、 氢气 作用下， 以 甲苯 为溶剂， 115.0 ℃ 、506.66 kPa 条件下， 反应 120.0h， 生成 (1R,2R,4R)-N-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine
  参考文献：
  名称：

  使用B（C6F5）3进行亚胺的无金属非对映选择性催化氢化。

  摘要：

  H（2）下催化量的B（C（6）F（5））（3）催化的手性酮亚胺的还原导致中等至极好的非对映选择性。对于樟脑和薄荷酮衍生的亚胺，还原反应的非对映选择性大于95％。

  DOI：

  10.1039/c1cc10438a
• 作为试剂：
  描述：

  扁桃酸 在 (1R,2R,4R)-N-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 以37%的产率得到D-扁桃酸
  参考文献：
  名称：

  Benzyl isobornyl amines: a simple and practical class of NMR discriminating agents for effective chiral recognition of acids

  摘要：

  The design and synthesis of a few simple N-benzyl derivatives of isobornyl amine is presented. The derivatives have been assessed as chiral solvating agents for effective discrimination of the signals of some acids in NMR analysis. The single crystal X-ray analysis of the salts of (R)-mandelic acid with two of the title derivatives help to understand the supramolecular interactions and assign the induced chemical shifts in H-1 NMR analysis. The title derivative is found to be suitable for quantitative determination of the enantiomeric excess of unknown enantiomeric purity as well as being efficient in resolving racemic mandelic acid. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.007

文献信息

• Direct Reductive Amination of Camphor Using Iron Pentacarbonyl as Stoichiometric Reducing Agent: Features and Limitations
  作者：Oleg I. Afanasyev、Artemy R. Fatkulin、Pavel N. Solyev、Ivan Smirnov、Artem Amangeldyev、Sergey E. Semenov、Denis Chusov

  DOI：10.1002/ejoc.202001087

  日期：2020.10.22

  direct reductive amination protocol of camphor and fenchone was developed. Scope and limitations of this protocol were studied. Primary amines react with high stereoselectivity while secondary cyclic amines lead to a mixture of endo‐(major) and exo‐(minor) adducts with a good to moderate yields.

  开发了樟脑和fenchone的直接还原胺化方案。研究了该协议的范围和局限性。伯胺具有很高的立体选择性，而仲环胺则可生成内（主要）和外（次要）加合物的混合物，产率中等至中等。
• Metal-free diastereoselective catalytic hydrogenations of imines using B(C6F5)3
  作者：Zachariah M. Heiden、Douglas W. Stephan

  DOI：10.1039/c1cc10438a

  日期：——

  Reductions of chiral ketimines effected under H(2) by catalytic amounts of B(C(6)F(5))(3) result in moderate to excellent diastereoselectivities. In the case of camphor and menthone derived imines, the reductions proceeded with greater than 95% diastereoselectivity.

  H（2）下催化量的B（C（6）F（5））（3）催化的手性酮亚胺的还原导致中等至极好的非对映选择性。对于樟脑和薄荷酮衍生的亚胺，还原反应的非对映选择性大于95％。
• Benzyl isobornyl amines: a simple and practical class of NMR discriminating agents for effective chiral recognition of acids
  作者：Jayaraman Kannappan、Aditya N. Khanvilkar、Gourav M. Upadhyay、Ashutosh V. Bedekar

  DOI：10.1016/j.tetasy.2017.08.007

  日期：2017.10

  The design and synthesis of a few simple N-benzyl derivatives of isobornyl amine is presented. The derivatives have been assessed as chiral solvating agents for effective discrimination of the signals of some acids in NMR analysis. The single crystal X-ray analysis of the salts of (R)-mandelic acid with two of the title derivatives help to understand the supramolecular interactions and assign the induced chemical shifts in H-1 NMR analysis. The title derivative is found to be suitable for quantitative determination of the enantiomeric excess of unknown enantiomeric purity as well as being efficient in resolving racemic mandelic acid. (C) 2017 Elsevier Ltd. All rights reserved.