(S)-4-benzylsulfanyl-4-(4-chlorophenyl)butan-2-one | 1115878-59-5

• 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-benzylsulfanyl-4-(4-chlorophenyl)butan-2-one
• 英文别名: (4S)-4-benzylsulfanyl-4-(4-chlorophenyl)butan-2-one
• CAS: 1115878-59-5
• 化学式: C₁₇H₁₇ClOS
• 分子量: 304.84
• InChiKey: JMBANEUGFWGYPX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  4-氯苯亚甲基丙酮 、 苄硫醇 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 24.17h， 以87%的产率得到(S)-4-benzylsulfanyl-4-(4-chlorophenyl)butan-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

• Organocatalytic Asymmetric Sulfa‐Michael Addition to α,β‐Unsaturated Ketones
  作者：Paolo Ricci、Armando Carlone、Giuseppe Bartoli、Marcella Bosco、Letizia Sambri、Paolo Melchiorre

  DOI：10.1002/adsc.200700382

  日期：2008.1.4

  The highly enantioselective organocatalytic sulfa-Michael addition to α,β-unsaturated ketones has been accomplished using benzyl and tert-butyl mercaptans as the sulfur-centered nucleophiles. Optically active products are obtained in high yields and good to excellent stereocontrol (up to 96 % ee) from a large variety of enones. Central to these studies has been the use of the catalytic primary amine

  使用苄基和叔丁基硫醇作为以硫为中心的亲核试剂，已经完成了对α，β-不饱和酮的高对映选择性有机催化磺胺-迈克尔加成反应。从多种烯酮中以高收率和良好至优异的立体控制（高达96％ee）获得光学活性产品。这些研究的核心是衍生自9-氨基-（9-脱氧）-表氢对苯二酚和D - N - Boc-苯基甘氨酸的催化伯胺盐A的使用，其中阳离子和阴离子均为手性，对烯酮的亚胺离子催化具有高反应活性和选择性。
• Sc(III)-Catalyzed Enantioselective Addition of Thiols to α,β-Unsaturated Ketones in Neutral Water
  作者：Simona Bonollo、Daniela Lanari、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/ol200379r

  日期：2011.5.6

  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.