(R)-4-phenyl-4-phenylsulfanylbutan-2-one | 78343-36-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-4-phenyl-4-phenylsulfanylbutan-2-one
• 英文别名: (4R)-4-phenyl-4-phenylsulfanylbutan-2-one
• CAS: 78343-36-9
• 化学式: C₁₆H₁₆OS
• 分子量: 256.368
• InChiKey: MZXMQFZIMHARKM-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯硫酚 、 苄叉丙酮 在 (αR,αR)-α,α-双(叔丁基)-[2,2-联吡啶]-6,6-二甲醇 、 scandium tris(trifluoromethanesulfonate) 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.17h， 以72%的产率得到(S)-4-phenyl-4-phenylsulfanylbutan-2-one
  参考文献：
  名称：

  Sc(III)-Catalyzed Enantioselective Addition of Thiols to α,β-Unsaturated Ketones in Neutral Water

  摘要：

  This report concerns Lewis acid catalyzed enantioselective sulfa-Michael addition in neutral water by using a very efficient Sc(OTf)(3)/bipyridine 1 catalytic system. It is noteworthy that the protocol presented employs water as a reaction medium and allows us to obtain very high stereoselectivity and satisfactory yields for beta-keto sulphides deriving from aliphatic thiols. The recovery and reuse of both the aqueous medium and the catalytic system is also reported.

  DOI：

  10.1021/ol200379r

文献信息

• Stereoselective thio-Michael addition to chalcones in water catalyzed by bovine serum albumin
  作者：Nicoletta Gaggero、Domenico Carlo Maria Albanese、Giuseppe Celentano、Stefano Banfi、Alice Aresi

  DOI：10.1016/j.tetasy.2011.06.024

  日期：2011.6

  A biomimetic, inexpensive, and simple method for the stereoselective thio-Michael addition of thiols to chalcones has been developed using bovine serum albumin (BSA) as a catalyst. Optically active products are obtained in high yield and with enantiomeric excesses of up to 70%. (C) 2011 Elsevier Ltd. All rights reserved.