(3R,4S)-3-benzoyl-4-ethylchroman-2-one | 1194476-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S)-3-benzoyl-4-ethylchroman-2-one
• CAS: 1194476-54-4
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: UPLYDGZIOPBSAT-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-苯甲酰基香豆素 、 三乙基铝 在 (R,R)-(PhMeCH)2N-P(-2-O-3,5-diMe-C₆H₂-C₆H₂-3',5'-diMe-2'-O-) 、 copper(II) acetate monohydrate 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 (3R,4S)-3-benzoyl-4-ethylchroman-2-one 、 3-benzoyl-4-ethylchroman-2-one
  参考文献：
  名称：

  Asymmetric conjugate additions to 1,1′-diactivated cyclic enones—a comparative study

  摘要：

  A study of copper-phosphoramidite-catalysed ZnR2 and AlR3 additions to 1,1'-dicarbonyl-activated cyclic Michael acceptors has revealed high enantioselectivities for AlR3 (R = Me, Et) 1,4-addition to a range of 3-acylcoumarins (85-98% ee, trans:cis similar to 90:10) using commercial OF readily available ligands. Large substituents at the 6-position, and to some extent at the 5-position, of the coumarin are less well tolerated, nor is truncation of the coumarin motif to a comparable 2-acylcyclohexenone (ee values up to 78%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.006

文献信息

• Organocatalytic Asymmetric Addition of Aromatic α-Cyanoketones to <i>o</i>-Quinone Methides: Synthesis of 3,4-Dihydrocoumarins and Tetrasubstituted Chromans
  作者：Chandan Gharui、Chandrakanta Parida、Subhas Chandra Pan

  DOI：10.1021/acs.joc.1c00435

  日期：2021.9.17

  The first organocatalytic asymmetric addition of aromatic α-cyanoketones to in situ-generated o-quinone methides has been developed. The products 3,4-dihydrocoumarin and tetrasubstituted chroman were obtained via addition of aromatic α-cyanoketones to in situ-generated o-quinone methides followed by treatment with 0.7 N HCl. With 10 mol % catalyst, the desired products were obtained in high enantio-

  第一有机催化不对称加成芳香α-cyanoketones的到在situ-产生ö -quinone甲基化物已被开发。产品3,4-二氢香豆素和四取代的苯并二氢吡喃是通过加入芳香α-cyanoketones的获得在situ-产生ö -quinone甲基化物，然后用0.7N的HCl处理。使用 10 mol% 的催化剂，以高对映选择性和非对映选择性获得所需产物。