(S)-6-Chloro-3-methyl-chroman-4-one | 141921-59-7

• 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: (S)-6-Chloro-3-methyl-chroman-4-one
• 英文别名: (3S)-6-chloro-3-methyl-2,3-dihydrochromen-4-one
• CAS: 141921-59-7
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: XZYWJEGILOPDJG-LURJTMIESA-N

物化性质

• 沸点：
  322.1±42.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  ethyl α-p-chlorophenoxymethylacrylate 在 palladium on activated charcoal 、 钯 甲烷磺酸 、 (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 、 甲苯 、 乙腈 为溶剂， 反应 13.5h， 生成 (S)-6-Chloro-3-methyl-chroman-4-one
  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

• Enantioselective preparation of 2-alkyl-3-aryloxypropionic acids and esters and 3-alkyl-4-chromanones
  作者：Bernard Loubinoux、Christine Viriot-Chauveau、J.L. Sinnes

  DOI：10.1016/0040-4039(92)88162-x

  日期：1992.4

  Lipases provided access to chiral 2-alkyl-3-aryloxypropionic acids that gave chiral 3-alkyl-4-chromanones with high enantioselectivity.
• 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.