1-methylthio-4-hydroxy-4-(3',5'-bis-trifluoromethylphenyl)-butan-2-one

• 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: 1-methylthio-4-hydroxy-4-(3',5'-bis-trifluoromethylphenyl)-butan-2-one
• 英文别名: 4-[3,5-Bis(trifluoromethyl)phenyl]-4-hydroxy-1-methylsulfanylbutan-2-one
• 化学式: C₁₃H₁₂F₆O₂S
• 分子量: 346.293
• InChiKey: GNUKJWWMTDZRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-甲基硫代-2-丙酮 、 3,5-双三氟甲基苯甲醛 在 (2R,3R,3'S)-2-hydroxy-3-[(pyrrolidine-2-carbonyl)amino]succinic acid diethyl ester 作用下， 以 二氯甲烷 为溶剂， 反应 124.0h， 以77%的产率得到1-methylthio-4-hydroxy-4-(3',5'-bis-trifluoromethylphenyl)-butan-2-one
  参考文献：
  名称：

  l-Proline amides catalyze direct asymmetric aldol reactions of aldehydes with methylthioacetone and fluoroacetone

  摘要：

  Direct aldol reactions of aldehydes with methylthio- and fluoroacetone catalyzed by proline amides have been investigated. L-Prolinamide 5e was found to be the best catalyst. Under the optimized reaction conditions, a series of aromatic and aliphatic aldehydes reacted smoothly with methylthioacetone, to generate 1-methylthio-4-hydroxyketones 3 in good yields and with high regio- and enantioselectivities. Excellent enantioselectivities of up to 98% ee were observed for aromatic aldehydes and even higher enantioselectivities of > 99% ee were observed for aliphatic aldehydes. Asymmetric direct aldol reactions of fluoroacetone with aldehydes in the presence of 20 mol % of 5e preferentially occurred at the fluoromethyl group, yielding products with high enantioselectivities (up to 98% ee). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.021

文献信息

• l-Proline amides catalyze direct asymmetric aldol reactions of aldehydes with methylthioacetone and fluoroacetone
  作者：Xiao-Ying Xu、Yan-Zhao Wang、Lin-Feng Cun、Liu-Zhu Gong

  DOI：10.1016/j.tetasy.2007.01.021

  日期：2007.2

  Direct aldol reactions of aldehydes with methylthio- and fluoroacetone catalyzed by proline amides have been investigated. L-Prolinamide 5e was found to be the best catalyst. Under the optimized reaction conditions, a series of aromatic and aliphatic aldehydes reacted smoothly with methylthioacetone, to generate 1-methylthio-4-hydroxyketones 3 in good yields and with high regio- and enantioselectivities. Excellent enantioselectivities of up to 98% ee were observed for aromatic aldehydes and even higher enantioselectivities of > 99% ee were observed for aliphatic aldehydes. Asymmetric direct aldol reactions of fluoroacetone with aldehydes in the presence of 20 mol % of 5e preferentially occurred at the fluoromethyl group, yielding products with high enantioselectivities (up to 98% ee). (c) 2007 Elsevier Ltd. All rights reserved.