[(4S,5S)-2-(2-methylsulfanylphenyl)-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol | 160246-26-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [(4S,5S)-2-(2-methylsulfanylphenyl)-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• CAS: 160246-26-4
• 化学式: C₁₇H₁₇NO₂S
• 分子量: 299.393
• InChiKey: BEZSXQVUKMKQBQ-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4S,5S)-2-(2-methylsulfanylphenyl)-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol 在 丙烯酸苄酯 、 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 endo-benzyl bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  Auxiliary accelerated reactions: Towards the use of catalytic chiral auxiliaries

  摘要：

  In competition experiments, the acceleration of reactivity of alkenes tethered to pyridyl groups compared with the corresponding alkenes tethered to phenyl groups in the presence of transition metals was demonstrated for two reaction types: Diels-Alder cycloaddition of enoate esters and catalytic hydrogenation of allylic and homoallylic ethers. The rate accelerations observed are of crucial importance in the development of a new concept for asymmetric catalysis: chiral auxiliaries which can function in a catalytic manner. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00829-6
• 作为产物：
  描述：

  2-(甲硫基)苯甲腈 、 (1S,2S)-(+)-2-氨基-1-苯基-1,3-丙二醇 在 potassium carbonate 作用下， 以 乙二醇 、 甘油 为溶剂， 反应 18.0h， 以47%的产率得到[(4S,5S)-2-(2-methylsulfanylphenyl)-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
  参考文献：
  名称：

  Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

  摘要：

  用对映纯的二氢噁唑辅基实现了硫化物向亚磺酰胺的非对映选择性氧化。当存在额外的羟甲基取代基时，非对映选择性非常高，1,5-不对称诱导可达到96:4的选择性，而在没有额外的手性试剂的情况下，1,6-不对称诱导可达到97:3的选择性。

  DOI：

  10.1039/p19960000333

文献信息

• Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction
  作者：Justin F. Bower、Christopher J. Martin、David J. Rawson、Alexandra M. Z. Slawin、Jonathan M. J. Williams

  DOI：10.1039/p19960000333

  日期：——

  The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96 : 4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97 : 3 selectivity in the absence of any additional chiral agents.

  用对映纯的二氢噁唑辅基实现了硫化物向亚磺酰胺的非对映选择性氧化。当存在额外的羟甲基取代基时，非对映选择性非常高，1,5-不对称诱导可达到96:4的选择性，而在没有额外的手性试剂的情况下，1,6-不对称诱导可达到97:3的选择性。
• Diastereoselective oxidation of arylsulfides
  作者：Justin F Bower、Jonathan Mj Williams

  DOI：10.1016/0040-4039(94)88239-8

  日期：1994.9

  Arylsulfides containing an enantiomerically pure oxazoline in the ortho-position have been oxidised to the corresponding sulfoxides with a variety of reagents. When the oxazoline unit contains a 4-hydroxymethyl group, good levels of diastereocontrol have been obtained using mCPBA (96:4) or t-butylhydroperoxide and titanium tetraisopropoxide (97:3) as the oxidant. This diastereocontrol provides an effective

  在邻位含有对映体纯的恶唑啉的芳基硫醚已用多种试剂氧化为相应的亚砜。当恶唑啉单元包含4-羟甲基时，使用mCPBA（96：4）或叔丁基氢过氧化物和四异丙氧基钛（97：3）作为氧化剂已获得了良好的非对映异构控制水平。这种非对映控制提供了1，6-不对称诱导的有效实例。
• Auxiliary accelerated reactions: Towards the use of catalytic chiral auxiliaries
  作者：Andrew D. Westwell、Jonathan M.J. Williams

  DOI：10.1016/s0040-4020(97)00829-6

  日期：1997.9

  In competition experiments, the acceleration of reactivity of alkenes tethered to pyridyl groups compared with the corresponding alkenes tethered to phenyl groups in the presence of transition metals was demonstrated for two reaction types: Diels-Alder cycloaddition of enoate esters and catalytic hydrogenation of allylic and homoallylic ethers. The rate accelerations observed are of crucial importance in the development of a new concept for asymmetric catalysis: chiral auxiliaries which can function in a catalytic manner. (C) 1997 Elsevier Science Ltd.