(3S,4S)-2,2-dimethyl-4-nitromethylchroman-3-carbaldehyde | 1122077-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3S,4S)-2,2-dimethyl-4-nitromethylchroman-3-carbaldehyde
• 英文别名: (3S,4S)-2,2-dimethyl-4-(nitromethyl)-3,4-dihydrochromene-3-carbaldehyde
• CAS: 1122077-36-4
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: BOVHRWFSBLTCKY-MNOVXSKESA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  377.6±42.0 °C(predicted)
• 密度：
  1.209±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-2,2-dimethyl-4-nitromethylchroman-3-carbaldehyde 、 4-溴肉桂醛 以 氯仿 为溶剂， 反应 24.0h， 以52%的产率得到(6aS,9R,10R,10aS)-9-(4-bromophenyl)-6,6-dimethyl-10-nitro-6a,9,10,10a-tetrahydrobenzo[c]chromene-8-carbaldehyde
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Conicol via Cascade Three-Component Organocatalysis

  摘要：

  The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.

  DOI：

  10.1021/ol902840x
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 反-2-羟基-β-硝基苯乙烯 在 (S)-2-(allyloxydiphenylmethyl)pyrrolidine grafted on mercaptopropyl functionalized mesoporous siliceous material 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以55%的产率得到(3S,4S)-2,2-dimethyl-4-nitromethylchroman-3-carbaldehyde
  参考文献：
  名称：

  通过介孔二氧化硅表面上的接枝手性碱和固有羟基协同催化的氧杂-迈克尔-迈克尔级联反应异构化对苯并二氢吡喃

  摘要：

  已经开发了一种多相对映选择性的氧杂-Michael-Michael反应，用于合成苯并二氢吡喃，该反应以固有的二氧化硅为酸性位点和固定的手性胺为碱性位点的多相酸碱协同催化剂为基础。与2-硝基乙烯基苯酚和3-甲基-2-丁烯醛相比，最终产品具有高达98％的选择性和ee达97％的选择性。还研究了多相协同催化机理。

  DOI：

  10.1039/c7cc03556j

文献信息

• Enantioselective Total Synthesis of (+)-Conicol via Cascade Three-Component Organocatalysis
  作者：Bor-Cherng Hong、Prakash Kotame、Chih-Wei Tsai、Ju-Hsiou Liao

  DOI：10.1021/ol902840x

  日期：2010.2.19

  The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.
• Heterogeneous enantioselective synthesis of chromans via the oxa-Michael–Michael cascade reaction synergically catalyzed by grafted chiral bases and inherent hydroxyls on mesoporous silica surface
  作者：Shanshan Wang、Jing He、Zhe An

  DOI：10.1039/c7cc03556j

  日期：——

  A heterogeneous enantioselective oxa-Michael–Michael reaction for the synthesis of chromans has been developed on a heterogeneous acid–base synergic catalyst with inherent silica as acidic sites and immobilized chiral amines as basic sites. Final products were afforded in selectivity of up to 98% and ee of 97% from 2-nitrovinyl phenol and 3-methyl-2-butenal. The heterogeneous synergistic catalytic

  已经开发了一种多相对映选择性的氧杂-Michael-Michael反应，用于合成苯并二氢吡喃，该反应以固有的二氧化硅为酸性位点和固定的手性胺为碱性位点的多相酸碱协同催化剂为基础。与2-硝基乙烯基苯酚和3-甲基-2-丁烯醛相比，最终产品具有高达98％的选择性和ee达97％的选择性。还研究了多相协同催化机理。