1-(S)-para-tolylsulfinyl-3,4-(methylenedioxy)benzene | 1224889-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(S)-para-tolylsulfinyl-3,4-(methylenedioxy)benzene
• 英文别名: 5-[(S)-(4-methylphenyl)sulfinyl]-1,3-benzodioxole
• CAS: 1224889-22-8
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: XMSZPCJOEHLIFA-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(S)-para-tolylsulfinyl-3,4-(methylenedioxy)benzene 在 lithium diisopropyl amide 、 iron(III) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.17h， 以82%的产率得到2,3,2',3'-di(methylenedioxy)-6,6'-bis(p-tolylsulfinyl)biphenyl
  参考文献：
  名称：

  Highly Effective and Diastereoselective Synthesis of Axially Chiral Bis-sulfoxide Ligands via Oxidative Aryl Coupling

  摘要：

  A series of axially chiral bis-sulfoxide ligands have been efficiently synthesized via oxidative coupling with high diastereoselectivities. The axial chirality is well controlled by the tert-butylsulfinyl or the p-tolylsulfinyl group. These axially chiral bis-sulfoxides proved to be remarkably efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to 2-cyclohexenone with 99% ee.

  DOI：

  10.1021/ol100536e
• 作为产物：
  描述：

  4-溴-1,2-亚甲二氧基苯 、 (1S,2R,5S)-(+)-menthyl (R)-p-toluenesulfinate 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 以70%的产率得到1-(S)-para-tolylsulfinyl-3,4-(methylenedioxy)benzene
  参考文献：
  名称：

  Highly Effective and Diastereoselective Synthesis of Axially Chiral Bis-sulfoxide Ligands via Oxidative Aryl Coupling

  摘要：

  A series of axially chiral bis-sulfoxide ligands have been efficiently synthesized via oxidative coupling with high diastereoselectivities. The axial chirality is well controlled by the tert-butylsulfinyl or the p-tolylsulfinyl group. These axially chiral bis-sulfoxides proved to be remarkably efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to 2-cyclohexenone with 99% ee.

  DOI：

  10.1021/ol100536e

文献信息

• Highly Effective and Diastereoselective Synthesis of Axially Chiral Bis-sulfoxide Ligands via Oxidative Aryl Coupling
  作者：Qing-An Chen、Xiang Dong、Mu-Wang Chen、Duo-Sheng Wang、Yong-Gui Zhou、Yu-Xue Li

  DOI：10.1021/ol100536e

  日期：2010.5.7

  A series of axially chiral bis-sulfoxide ligands have been efficiently synthesized via oxidative coupling with high diastereoselectivities. The axial chirality is well controlled by the tert-butylsulfinyl or the p-tolylsulfinyl group. These axially chiral bis-sulfoxides proved to be remarkably efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to 2-cyclohexenone with 99% ee.