(S)-(-)-N-(piperonylmethylidene)-p-toluenesulfinamide | 299183-66-7

• 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: (S)-(-)-N-(piperonylmethylidene)-p-toluenesulfinamide
• 英文别名: (NE,S)-N-(1,3-benzodioxol-5-ylmethylidene)-4-methylbenzenesulfinamide
• CAS: 299183-66-7
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: BDGSNJHFQQJHHC-ZYEUVFMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Butenylmagnesium bromide 、 (S)-(-)-N-(piperonylmethylidene)-p-toluenesulfinamide 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-Methyl-benzenesulfinic acid ((S)-1-benzo[1,3]dioxol-5-yl-pent-4-enyl)-amide 、 4-Methyl-benzenesulfinic acid ((R)-1-benzo[1,3]dioxol-5-yl-pent-4-enyl)-amide
  参考文献：
  名称：

  立体选择性加成至手性对甲苯磺胺类药物

  摘要：

  在铜盐的介导下，向手性对甲苯磺胺亚胺2b - 2d非对映选择性地添加了许多格氏试剂，得到了各种受保护的α-支化胺。

  DOI：

  10.1016/s0040-4039(00)00949-7
• 作为产物：
  描述：

  胡椒醛 、 (S)-(+)-对甲基苯亚磺酰胺 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以52%的产率得到(S)-(-)-N-(piperonylmethylidene)-p-toluenesulfinamide
  参考文献：
  名称：

  Synthesis of Enantiopure Sulfinimines (Thiooxime S-Oxides) Catalyzed by Yb(OTf)₃ from p-Toluenesulfinamide and Aldehydes in Mild Reaction Conditions

  摘要：

  Enantiomerically pure sulfinimines as important building blocks in the asymmetric synthesis of amine derivatives are prepared in good to excellent yields from chiral p-toluenesulfinamide with aromatic, heteroaromatic, and aliphatic aldehydes. The unprecedented feature of the reported procedure is that the formation of the sulfinimines was achieved by the catalytic action of Yb(OTf)(3) in THF at room temperature. The reaction conditions were also applicable to Ellman's sulfinimines.

  DOI：

  10.1021/jo048597e

文献信息

• Highly Diastereoselective Addition of the Lithium Enolate of α-Diazoacetoacetate to <i>N</i>-Sulfinyl Imines:  Enantioselective Synthesis of 2-Oxo and 3-Oxo Pyrrolidines
  作者：Changqing Dong、Fanyang Mo、Jianbo Wang

  DOI：10.1021/jo702275a

  日期：2008.3.1

  The highly enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines has been achieved by diastereoselective addition of the lithium enolate of α-diazoacetoacetate to chiral N-sulfinyl imines, followed by photoinduced Wolff rearrangement or Rh(II)-catalyzed intramolecular N−H insertion.

  通过将非对映体选择性地将α-重氮乙酰乙酸锂的烯醇锂添加到手性N-亚磺酰基亚胺中，然后进行光诱导的Wolff重排或Rh（II）催化的分子内NH，可以实现2-氧和3-氧吡咯烷的高度对映选择性合成。插入。
• Stereoselective addition to chiral p-toluene sulfinimines
  作者：Wing Hong Chan、Albert W.M Lee、Ping Fang Xia、Wai Yeung Wong

  DOI：10.1016/s0040-4039(00)00949-7

  日期：2000.7

  Diastereoselective addition of a number of Grignard reagents to chiral p-toluene sulfinimines 2b–2d under the mediation of copper salts afforded various protected α-branched amines.

  在铜盐的介导下，向手性对甲苯磺胺亚胺2b - 2d非对映选择性地添加了许多格氏试剂，得到了各种受保护的α-支化胺。
• Synthesis of Enantiopure Sulfinimines (Thiooxime <i>S</i>-Oxides) Catalyzed by Yb(OTf)₃ from <i>p</i>-Toluenesulfinamide and Aldehydes in Mild Reaction Conditions
  作者：Zhi-Yong Jiang、W. H. Chan、A. W. M. Lee

  DOI：10.1021/jo048597e

  日期：2005.2.1

  Enantiomerically pure sulfinimines as important building blocks in the asymmetric synthesis of amine derivatives are prepared in good to excellent yields from chiral p-toluenesulfinamide with aromatic, heteroaromatic, and aliphatic aldehydes. The unprecedented feature of the reported procedure is that the formation of the sulfinimines was achieved by the catalytic action of Yb(OTf)(3) in THF at room temperature. The reaction conditions were also applicable to Ellman's sulfinimines.