6-tert-butyl-3-methyl-4-chromanone | 646064-62-2

• 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: 6-tert-butyl-3-methyl-4-chromanone
• 英文别名: 6-tert-Butyl-3-methyl-2,3-dihydro-4H-1-benzopyran-4-one；6-tert-butyl-3-methyl-2,3-dihydrochromen-4-one
• CAS: 646064-62-2
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: GYROGDBBRVOADH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-tert-butyl-3-methyl-4-chromanone 在 钯 (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 (R)-6-tert-butyl-3-methyl-4-chromanone
  参考文献：
  名称：

  Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step

  摘要：

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.095
• 作为产物：
  描述：

  2-(4-tert-Butyl-phenoxymethyl)-acrylic acid ethyl ester 在 palladium on activated charcoal 三氟甲磺酸 、 氢气 作用下， 以 乙腈 为溶剂， 反应 1.3h， 生成 6-tert-butyl-3-methyl-4-chromanone
  参考文献：
  名称：

  Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step

  摘要：

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.095

文献信息

• Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step
  作者：Olivier Roy、François Loiseau、Abdelkhalek Riahi、Françoise Hénin、Jacques Muzart

  DOI：10.1016/j.tet.2003.09.095

  日期：2003.11

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.