(3R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one | 74408-99-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (3R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one
• 英文别名: (R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one；(R)-1,3-diphenyl-3-phenylsulfanylpropan-1-one；(R)-1,3-diphenyl-3-(phenylthio)propan-1-one；1,3-diphenyl-3-phenylsulfanyl-propan-1-one；1,3-diphenyl-3-(phenylthio)propan-1-one；(3R)-1,3-diphenyl-3-phenylsulfanylpropan-1-one
• CAS: 74408-99-4
• 化学式: C₂₁H₁₈OS
• 分子量: 318.439
• InChiKey: XFMOIXTZMKSAPF-OAQYLSRUSA-N

物化性质

• 熔点：
  96-97 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• 沸点：
  493.0±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以95%的产率得到(+)-(R)-1,3-diphenyl-3-phenylsulfonylpropan-1-one
  参考文献：
  名称：

  A new and efficient route to homochiral γ-hydroxysulfoxides and γ-hydroxysulfones

  摘要：

  Readily available (+)- (R)-1,3-diphenyl-3-phenylsulfanyl-propan-1-one 1 was oxidized to the corresponding sulfone and its reduction gave separable (1R,3R)- and (1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ols. When I was reduced to the mixture of epimeric alcohols, subsequent reaction with three different sulfoxidation agents allowed the separation of all four diastereomeric, 1,3-diphenyl-3-phenylsulfinylpropan-1-ols in diastereomerically pure form. The absolute configuration at the newly created stereogenic carbon was proved by chemical correlation, while the configuration of the sulfur centre of the phenylsulfinyl group was established by CD spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00581-5
• 作为产物：
  描述：

  苯硫酚 、 反式-查耳酮 在 辛可宁 作用下， 以70%的产率得到(3R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one
  参考文献：
  名称：

  通过氧和氮亲核试剂分子内取代噻吩氧化物的闭环反应：4,5-二氢异恶唑和4,5-二氢吡唑的简单立体定向合成

  摘要：

  报道了一种新的，简单的方法，该方法可以从苯硫酚的手性迈克尔加合物向查耳酮的易获得的肟中立体定向合成3,5-二取代的4,5-二氢-异恶唑（手性异恶唑啉）。与迈克尔加成物的N-芳基hydr类似的反应得到非外消旋的1-（芳基）-3,5-二苯基-4,5-二氢-1H-吡唑（手性吡唑啉），但是这些产物构型不稳定。合成的关键步骤是闭环反应，该反应通过噻吩氧化物的立体特异性分子内亲核取代而发生。

  DOI：

  10.1016/j.tet.2005.03.085

文献信息

• Synthesis and Resolution of a Multifunctional Inherently Chiral Calix[4]arene with an ABCD Substitution Pattern at the Wide Rim: The Effect of a Multifunctional Structure in the Organocatalyst on Enantioselectivity in Asymmetric Reactions
  作者：Seiji Shirakawa、Tomohiro Kimura、Shun-ichi Murata、Shoichi Shimizu

  DOI：10.1021/jo8024412

  日期：2009.2.6

  synthetic route to inherently chiral calix[4]arenes with an ABCD substitution pattern at the wide rim in the cone conformation was developed for the first time. For the synthesis of inherently chiral ABCD-type calix[4]arenes, first 5,11-dibromo-17-(3,5-dimethylphenyl)-25,26,27,28-tetrapropoxycalix[4]arene (9) was prepared as a key intermediate. Then, functionalization of the calix[4]arene 9 was examined

  首次开发了一种有效的合成路线，以固有的手性杯[4]芳烃在圆锥构象的宽边具有ABCD取代模式。为了合成固有手性ABCD型杯[4]芳烃，首先制备了5,11-二溴-17-（3,5-二甲基苯基）-25,26,27,28-四丙氧基杯[4]芳烃（9）作为关键的中间产物。然后，对杯[4]芳烃9进行功能化进行了检查，并通过溴基团的选择性单锂化实现了高度区域选择性的单官能化。用这种方法可以合成各种多功能的手性ABCD型杯芳烃[4]芳烃。因此，证明了ABCD型杯[4]芳烃固有的手性膦和羧酸衍生物的合成。另外，合成了在宽边缘具有3，5-二甲基苯基的ABCD型杯[4]芳烃的氨基苯酚衍生物1b，并将其拆分为光学纯的对映体。手性杯[4]芳烃1b在苯酚的不对称迈克尔加成反应中用作有机催化剂。3,5-二甲基苯基在杯[4]芳烃1b的宽边缘上的作用 考察了对映体对映体的对映体选择性，并观察到了3，5-二甲基苯基的积极作用。
• 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。
• A Bifunctional Cinchona Alkaloid-Squaramide Catalyst for the Highly Enantioselective Conjugate Addition of Thiols to trans-Chalcones
  作者：Le Dai、Su-Xi Wang、Fen-Er Chen

  DOI：10.1002/adsc.201000334

  日期：2010.9.10

  A chiral squaramide catalysts‐promoted asymmetric sulfa‐Michael conjugated addition of thiols to trans‐chalcones is presented. Moderate to excellent yields and high enantioselectivities (up to 99% ee) were achieved under mild conditions.

  提出了一种手性方酰胺催化剂促进的不对称磺胺-迈克尔共轭硫醇到反式查尔酮的加成反应。在温和的条件下，获得了中度至优异的收率和高对映选择性（高达99％ee）。
• Improved design of inherently chiral calix[4]arenes as organocatalysts
  作者：Seiji Shirakawa、Shoichi Shimizu

  DOI：10.1039/b9nj00685k

  日期：——

  design of inherently chiral calix[4]arenes as organocatalysts was accomplished via the introduction of a diarylmethanol structure. Novel, inherently chiral calix[4]arenes bearing a tertiary amine or a quaternary ammonium moiety, together with a diarylmethanol moiety, were synthesized from previously reported chiral calix[4]arene amino acid derivatives in an optically pure form. These chiral calix[4]arenes

  通过引入二芳基甲醇结构可以改善固有手性杯[4]芳烃作为有机催化剂的设计。带有叔胺或季铵盐的新型固有手性杯[4]芳烃铵盐 由先前报道的手性合成部分与二芳基甲醇部分 杯[4]芳烃氨基酸光学纯形式的衍生物。这些手性杯[4]芳烃作为有机催化剂应用于不对称反应，并观察到二芳基甲醇结构对对映选择性的积极作用。