(1R,2S,3S,4R,4aS,8aS)-4-(4-bromophenyl)-8a-hydroxy-3-nitro-2-phenyldecahydronaphthalene-1-carbaldehyde | 1288984-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,3S,4R,4aS,8aS)-4-(4-bromophenyl)-8a-hydroxy-3-nitro-2-phenyldecahydronaphthalene-1-carbaldehyde
• 英文别名: (1R,2S,3S,4R,4aS,8aS)-4-(4-bromophenyl)-8a-hydroxy-3-nitro-2-phenyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalene-1-carbaldehyde
• CAS: 1288984-87-1
• 化学式: C₂₃H₂₄BrNO₄
• 分子量: 458.352
• InChiKey: SZVOXLYSEJJFCZ-NVNANWAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 (2S)-2-((1R)-1-(4-bromophenyl)-2-nitroethyl)cyclohexanone 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以75%的产率得到(1R,2S,3S,4R,4aS,8aS)-4-(4-bromophenyl)-8a-hydroxy-3-nitro-2-phenyldecahydronaphthalene-1-carbaldehyde
  参考文献：
  名称：

  Organocatalytic Synthesis of Multiple Substituted Bicyclo[4.4.0]Decalin System

  摘要：

  An efficient and unprecedented organocatalytic reaction of gamma-nitroketones with alpha,beta-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to > 99:1 dr and > 99% ee) via a formal [4 + 2] carbocyclization process.

  DOI：

  10.1021/ol200424x

文献信息

• Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts
  作者：Guangning Ma、Shuangzheng Lin、Ismail Ibrahem、Grzegorz Kubik、Leifeng Liu、Junliang Sun、Armando Córdova

  DOI：10.1002/adsc.201200357

  日期：2012.10.8

  approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic γ-nitro ketones and α,β-unsaturated aldehydes using different achiral co-catalysts. The utility of the method is

  公开了一种立体化学发散方法，其使用单一手性催化剂从外消旋物高度对映选择性地合成具有多个立体中心的独特的双环产物。它基于使用不同的非手性助催化剂在外消旋γ-硝基酮和α，β-不饱和醛之间进行手性胺催化的级联反应中整体反应路径的转换。该方法的实用性是通过手性胺和非手性氢键给体催化剂的组合进行非对映选择性高的转换和立体收敛的脱硝过程来举例说明的。