(6aS,9R,10R,10aS)-9-(dimethoxymethyl)-2-hydroxy-6,6-dimethyl-10-nitro-6a,9,10,10a-tetrahydrobenzo[c]chromene-8-carbaldehyde | 1207377-04-5

• 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: (6aS,9R,10R,10aS)-9-(dimethoxymethyl)-2-hydroxy-6,6-dimethyl-10-nitro-6a,9,10,10a-tetrahydrobenzo[c]chromene-8-carbaldehyde
• CAS: 1207377-04-5
• 化学式: C₁₉H₂₃NO₇
• 分子量: 377.394
• InChiKey: ZGSYWBYSMVLOGH-SVGFKBNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6aS,9R,10R,10aS)-9-(dimethoxymethyl)-2-hydroxy-6,6-dimethyl-10-nitro-6a,9,10,10a-tetrahydrobenzo[c]chromene-8-carbaldehyde 在 Wilkinson's catalyst 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以54%的产率得到(6aS,9R,10R,10aS)-9-(dimethoxymethyl)-6,6-dimethyl-10-nitro-6a,9,10,10a-tetrahydrobenzo[c]chromen-2-ol
  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：

  4,4-二甲氧基-2-丁烯醛 、 (3S,4S)-6-hydroxy-2,2-dimethyl-4-(nitromethyl)chromane-3-carbaldehyde 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 35.0h， 以69%的产率得到(6aS,9R,10R,10aS)-9-(dimethoxymethyl)-2-hydroxy-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

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.