(S)-4-(4'-chlorophenyl)-3-methyl-butan-2-one | 1101197-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-(4'-chlorophenyl)-3-methyl-butan-2-one
• 英文别名: (3S)-4-(4-chlorophenyl)-3-methylbutan-2-one
• CAS: 1101197-89-0
• 化学式: C₁₁H₁₃ClO
• 分子量: 196.677
• InChiKey: PPFQLGFSWPJTGJ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-4-(4-chlorophenyl)-3-methyl-3-buten-2-one 在 ((4S)-2-(2-(diphenylphosphino)phenyl)-4-tert-butyl-4,5-dihydrooxazole)-(η4-1,5-cyclooctadiene)iridium(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 、 氢气 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 3.0h， 以92%的产率得到(S)-4-(4'-chlorophenyl)-3-methyl-butan-2-one
  参考文献：
  名称：

  铱催化的不对称加氢反应对光学活性酮的高度对映选择性合成。

  摘要：

  DOI：

  10.1002/anie.200803709

文献信息

• Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
  作者：Bruno R.S. de Paula、Dávila S. Zampieri、J. Augusto R. Rodrigues、Paulo J.S. Moran

  DOI：10.1016/j.tetasy.2013.07.007

  日期：2013.9

  Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten-2-one (R = n-pentyl, phenyl, 2'- and 4'-chlorophenyl, 3'- and 4'-nitrophenyl, 4'-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae and Geotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.
• Extractive biocatalysis in the asymmetric reduction of α-alkyl, β-aryl enones by Baker’s yeast
  作者：Rafaela M. Silva、Laura T. Okano、J. Augusto R. Rodrigues、Giuliano C. Clososki

  DOI：10.1016/j.tetasy.2017.05.009

  日期：2017.7

  We prepared various chiral alpha-alkyl, beta-aryl ketones with good to excellent enantiomeric excess through the Baker's yeast asymmetric double-bond reduction of the corresponding alpha,beta-unsaturated substrates adsorbed onto the resin Amberlite XAD-7. This methodology was compatible with substrates bearing both electron-donating and withdrawing groups attached to the aromatic ring. Elongation of the alpha-alkyl substituent of the starting material strongly affected the reactivity and enantioselectivity of the reaction. (C) 2017 Elsevier Ltd. All rights reserved.
• US4356024A
  申请人：——

  公开号：US4356024A

  公开（公告）日：1982-10-26
• Highly Enantioselective Synthesis of Optically Active Ketones by Iridium-Catalyzed Asymmetric Hydrogenation
  作者：Sheng-Mei Lu、Carsten Bolm

  DOI：10.1002/anie.200803709

  日期：2008.11.3