(R)-4-(benzylthio)nonan-2-one | 1115878-65-3

• 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: (R)-4-(benzylthio)nonan-2-one
• 英文别名: (R)-4-benzylsulfanylnonan-2-one；(4R)-4-benzylsulfanylnonan-2-one
• CAS: 1115878-65-3
• 化学式: C₁₆H₂₄OS
• 分子量: 264.432
• InChiKey: JGDOYLADVOSTIN-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-壬烯-2-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 6.17h， 以82%的产率得到(R)-4-(benzylthio)nonan-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

• Chiral Sc-catalyzed asymmetric Michael reactions of thiols with enones in water
  作者：Masaharu Ueno、Taku Kitanosono、Masaru Sakai、Shū Kobayashi

  DOI：10.1039/c1ob05424d

  日期：——

  Asymmetric Michael reactions of thiols with enones were catalyzed by a Sc(OTf)3–chiral bipyridine complex at room temperature in water without using any organic solvents, to afford the desired sulfides in high yields with high enantioselectivities.

  不对称的迈克尔反应中，硫醇与烯酮在室温下以水为溶剂，由Sc(OTf)3-手性双吡啶复合物催化，成功得到所需的硫化物，产率高且对映选择性高。
• Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water
  作者：Taku Kitanosono、Masaru Sakai、Masaharu Ueno、Shū Kobayashi

  DOI：10.1039/c2ob26264a

  日期：——

  Asymmetric Michael reactions and enantioselective protonations between enones and thiols were catalyzed by a Sc(OTf)3–chiral 2,2′-bipyridine complex in water. The remarkable governing of the enantioselectivity for simple introduction of protons despite their abnormally high mobility in water may provide us with new synthetic opportunities as well as significant chemical advances.

  Sc（OTf）3-手性2,2'-联吡啶配合物催化烯酮和硫醇之间的不对称迈克尔反应和对映选择性质子水。尽管质子的迁移率异常高，但对简单引入质子的对映选择性的显着控制。水 可能为我们提供新的合成机会以及重大的化学进展。
• 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。