(E)-3-(1,3-di-p-tolylallyl)-4-hydroxy-2H-chromen-2-one | 1379594-82-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-3-(1,3-di-p-tolylallyl)-4-hydroxy-2H-chromen-2-one
• 英文别名: 3-[(E)-1,3-bis(4-methylphenyl)prop-2-enyl]-4-hydroxychromen-2-one
• CAS: 1379594-82-7
• 化学式: C₂₆H₂₂O₃
• 分子量: 382.459
• InChiKey: GXUNGZYEZBLTRH-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(1,3-di-p-tolylallyl)-4-hydroxy-2H-chromen-2-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 1.0h， 以213 mg的产率得到2,4-di-p-tolyl-2H,5H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  HFIP Promoted C3 Alkylation of Lawsone and 4-Hydroxycoumarin with Alcohols by Dehydrative Cross-Coupling

  摘要：

  An environmentally benign system for the direct alkylation of lawsones and 4-hydroxycoumarins with alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is reported. The reaction proceeded smoothly via a dehydrative cross-coupling process by utilizing the unique properties of HFIP. A variety of alkylated products and subsequent one-pot cyclized products (pyranonaphthoquinones and pyranocoumarins) could be obtained in 40-93% yields.

  DOI：

  10.1021/acs.joc.0c01207
• 作为产物：
  描述：

  4-羟基香豆素 、 1,3-di(4'-tolyl)prop-2-en-1-ol 在 六氟异丙醇 作用下， 反应 0.17h， 以69%的产率得到(E)-3-(1,3-di-p-tolylallyl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  HFIP Promoted C3 Alkylation of Lawsone and 4-Hydroxycoumarin with Alcohols by Dehydrative Cross-Coupling

  摘要：

  An environmentally benign system for the direct alkylation of lawsones and 4-hydroxycoumarins with alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is reported. The reaction proceeded smoothly via a dehydrative cross-coupling process by utilizing the unique properties of HFIP. A variety of alkylated products and subsequent one-pot cyclized products (pyranonaphthoquinones and pyranocoumarins) could be obtained in 40-93% yields.

  DOI：

  10.1021/acs.joc.0c01207

文献信息

• First example of a heterobimetallic ‘Pd–Sn’ catalyst for direct activation of alcohol: efficient allylation, benzylation and propargylation of arenes, heteroarenes, active methylenes and allyl-Si nucleophiles
  作者：Debjit Das、Sanjay Pratihar、Ujjal Kanti Roy、Dipakranjan Mal、Sujit Roy

  DOI：10.1039/c2ob25275a

  日期：——

  Arenes, heteroarenes, 1,3-dicarbonyls and organosilicon nucleophiles undergo highly efficient alkylation with allylic, propargylic and benzylic alcohols in the presence of a new ‘Pd–Sn’ bimetallic catalyst in nitromethane; water being the sole byproduct. The plausible mechanism of alkylation and the intermediacy of ether has been enumerated.

  在新的“ Pd-Sn”双金属催化剂存在下，芳烃，杂芳烃，1,3-二羰基化合物和有机硅亲核试剂与烯丙基，炔丙基和苄基醇进行高效烷基化 硝基甲烷; 水是唯一的副产品。列举了烷基化的合理机理和醚的中间体。