(S)-N-ethylidene-4-methylbenzenesulfinamide | 919492-01-6

• 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: (S)-N-ethylidene-4-methylbenzenesulfinamide
• CAS: 919492-01-6
• 化学式: C₉H₁₁NOS
• 分子量: 181.258
• InChiKey: JYGZWWQQJIGSSI-LBPRGKRZSA-N

物化性质

• 沸点：
  322.7±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-N-ethylidene-4-methylbenzenesulfinamide 、 硝基甲烷 在 sodium hydroxide 作用下， 生成 N-p-tolylsulfinylnitroamine
  参考文献：
  名称：

  An Efficient Method for the Synthesis of Nitropiperidones

  摘要：

  [GRAPHICS]A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha, beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.

  DOI：

  10.1021/jo702130a
• 作为产物：
  描述：

  N-p-tolylsulfinylnitroamine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 丙烯酸乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-N-ethylidene-4-methylbenzenesulfinamide
  参考文献：
  名称：

  An Efficient Method for the Synthesis of Nitropiperidones

  摘要：

  [GRAPHICS]A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha, beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.

  DOI：

  10.1021/jo702130a

文献信息

• Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of <i>N</i>-Sulfinyl β-Amino Ketones. Formal Synthesis of (−)-Pinidinol and (+)- Epipinidinol
  作者：Franklin A. Davis、Paul M. Gaspari、Brad M. Nolt、Peng Xu

  DOI：10.1021/jo801653c

  日期：2008.12.19

  Stereoselective reduction of acyclic N-sulfinyl beta-amino ketones with (LiEt(3)BH) and Li(t-BuO)(3)AlH, respectively, gave anti- and syn-1,3-amino alcohols with excellent selectivity. A formal asymmetric synthesis of the hydroxy piperidine alkaloids (-)-pinidinol and (+)-epipinidinol from a common N-sulfinyl beta-amino ketone ketal precursor was developed. The pinidinol piperidine ring was formed

  分别用（LiEt（3）BH）和Li（t-BuO）（3）AlH立体选择性还原无环N-亚磺酰基β-氨基酮，得到具有优异选择性的抗和syn-1,3-氨基醇。从常见的N-亚磺酰基β-氨基酮缩酮前体开发了羟基哌啶生物碱（-）-吡啶醇和（+）-哌啶醇的形式不对称合成。吡啶醇哌啶环是通过N-亚磺酰基氨基甲硅烷基保护的醇缩酮的新型酸催化级联反应形成的。