acrylic acid 2,6-dimethoxyphenyl ester | 1528740-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: acrylic acid 2,6-dimethoxyphenyl ester
• 英文别名: syringyl vinyl ketone；syringyl acrylate；(2,6-Dimethoxyphenyl) prop-2-enoate；(2,6-dimethoxyphenyl) prop-2-enoate
• CAS: 1528740-16-0
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: JFQXQDSZHOMFIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-(1-nitroethyl)-phosphonate 、 acrylic acid 2,6-dimethoxyphenyl ester 在 3-(benzylamino)-4-(((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以92%的产率得到4-(diethoxyphosphoryl)-4-nitropentanoic acid 2,6-dimethoxyphenyl ester
  参考文献：
  名称：

  Cinchona based squaramide catalysed enantioselective Michael addition of α-nitrophosphonates to aryl acrylates: enantioselective synthesis of quaternary α-aminophosphonates

  摘要：

  Several cinchona based squaramide catalysts were applied to the asymmetric Michael addition of alpha-nitroethylphosphonates to acrylic acid aryl esters, resulting in high yields and enantioselectivities. The absolute configuration of one of the quaternary alpha-nitrophosphonate adducts was deduced from its experimental and calculated CD spectra. The adducts were reduced to their cyclic aminophosphonates by catalytic hydrogenation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.008

文献信息

• Diethyl (cyanofluoromethyl)phosphonate: Application in catalytic enantioselective Michael additions
  作者：Zsuzsa Jászay、István Tódor、Zsolt Rapi、Péter Bakó、Imre Petneházy、László Tőke

  DOI：10.1080/10426507.2017.1311334

  日期：2017.6.3

  GRAPHICAL ABSTRACT ABSTRACT Three types of chiral catalysts: a chincona-based squaramide, TADDOL and a group of sugar-based crown ethers were applied to the asymmetric Michael addition of diethyl (cyanofluoromethyl)phosphonate to diverse Michael acceptors. Two of the crown ether catalysts resulted in high yields and enantioselectivities with trans-β-nitostyrene as in case of the chincona-based squaramide

  图形摘要摘要 三种类型的手性催化剂：基于金科纳的方酸酰胺、TADDOL 和一组基于糖的冠醚被应用于（氰氟甲基）膦酸二乙酯与不同迈克尔受体的不对称迈克尔加成。两种冠醚催化剂在反式-β-硝基苯乙烯的情况下产生高产率和对映选择性，如在基于chincona的方酰胺催化剂的情况下，产率低且对映选择性高。TADDOL 被证明是活跃的，但在迈克尔加法中的选择性较低。
• WO2022272142A1
  申请人：——

  公开号：WO2022272142A1

  公开（公告）日：2022-12-29
• Cinchona based squaramide catalysed enantioselective Michael addition of α-nitrophosphonates to aryl acrylates: enantioselective synthesis of quaternary α-aminophosphonates
  作者：Truong Son Pham、Katalin Gönczi、György Kardos、Krisztina Süle、László Hegedűs、Mihály Kállay、Miklós Kubinyi、Pál Szabó、Imre Petneházy、László Tőke、Zsuzsa Jászay

  DOI：10.1016/j.tetasy.2013.10.008

  日期：2013.12

  Several cinchona based squaramide catalysts were applied to the asymmetric Michael addition of alpha-nitroethylphosphonates to acrylic acid aryl esters, resulting in high yields and enantioselectivities. The absolute configuration of one of the quaternary alpha-nitrophosphonate adducts was deduced from its experimental and calculated CD spectra. The adducts were reduced to their cyclic aminophosphonates by catalytic hydrogenation. (C) 2013 Elsevier Ltd. All rights reserved.