(1R,2R)-2-aminomethyl-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptane

• 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)-2-aminomethyl-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptane
• 英文别名: 2-aminomethyl-2-hydroxy-1,3,3-trimethyl-[2,2,1]-bicycloheptane；(1R,2R,4R)-2-(aminomethyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: AVVKCURHCXPDER-IEBDPFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘-3-甲基苯甲醛 、 (1R,2R)-2-aminomethyl-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptane 在 sodium sulfate 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以36%的产率得到(1R,2R,4R)-2'-(2-iodo-3-methylphenyl)-1,7,7-trimethyl-4'H-spiro[bicyclo[2.2.1]heptane-2,5'-oxazole]
  参考文献：
  名称：

  New chiral iodooxazoline catalysts for the I(III)-mediated α-tosyloxylation of ketones: refining the stereoinduction model

  摘要：

  A new family of iodooxazoline catalysts, derived from widely available chiral ketones (menthone and camphor), was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The reaction conditions to achieve the direct formation of the oxazoline moieties from the corresponding aminoalcohols and an aldehyde were explored and optimized. These catalysts were tested for the alpha-tosyloxylation of propiophenone and led to new information on the stereoinduction process. The results demonstrate that modulation of the steric hindrance around the iodane center is critical to obtain good activity. Additionally, from the selectivities observed, a preliminary predictive model is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.002
• 作为产物：
  描述：

  2-cyano-2-trimethylsilanyloxy-1,3,3-trimethyl-[2.2.1]-bicycloheptane 在 红铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (1R,2R)-2-aminomethyl-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  新的烷氧基锂可加速酮的非对映选择性氰化。

  摘要：

  [反应：见正文]已经发现，在醛和酮中添加了一种非常普通的锂杂原子辅助的TMSCN或TBSCN。该方法具有出色的选择性和高产率。构象受限制的酮，如樟脑，芬琴酮和诺品酮，与TMSCN的结合具有极好的非对映选择性。还原2以良好的产率提供了非对映体纯的氨基醇3。具有TBSCN-LiOR的α-和β-甲基环己酮具有很高的非对映选择性和收率。

  DOI：

  10.1021/ol0069608

文献信息

• Chiral β- and γ-aminoalcohols derived from (+)-camphor and (−)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde
  作者：Vladimir Dimitrov、Georgi Dobrikov、Miroslav Genov

  DOI：10.1016/s0957-4166(01)00221-x

  日期：2001.6

  The addition of Me3SiCN and LICH2CN to (+)-camphor and (-)-fenchone. respectively, followed by reduction leads to chiral beta- and gamma -aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et2Zn to benzaldehyde were lower than those obtained using the corresponding delta -aminoalcohols. (C) 2001 Elsevier Science Ltd. All rights reserved.