(Rs)-2-methyl-N-pentylidenepropane-2-sulfinamide | 849590-37-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (Rs)-2-methyl-N-pentylidenepropane-2-sulfinamide
• 英文别名: 2-methyl-N-pentylidenepropane-2-sulfinamide
• CAS: 849590-37-0
• 化学式: C₉H₁₉NOS
• 分子量: 189.322
• InChiKey: LUXHRMWIRCPVFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  285.2±23.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  O-tert-butyl-1,2-dichloroenol ether 、 (Rs)-2-methyl-N-pentylidenepropane-2-sulfinamide 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.75h， 以85%的产率得到(S_SR_S,RS)-N-(3-(tert-butoxy)hept-1-yn-3-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Asymmetric Addition of Alkoxy Ethynyl Anion to Chiral N-Sulfinyl Imines

  摘要：

  The addition of lithiated ynol ethers to chiral N-sulfinyl imines proceeds in high yield and diastereoselectivity. The selectivity is completely reversed by the addition of boron trifluoride. These alkoxypropargyl sulfinamides can be reduced to afford enol ethers, selectively oxidized to busyl derivatives, or the ynol ether can be hydrolyzed to afford beta-amino esters.

  DOI：

  10.1021/ol302392k
• 作为产物：
  描述：

  正戊醛 、 叔丁基亚磺酰胺 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以99%的产率得到(Rs)-2-methyl-N-pentylidenepropane-2-sulfinamide
  参考文献：
  名称：

  A General Aminocatalytic Method for the Synthesis of Aldimines

  摘要：

  A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.

  DOI：

  10.1021/ja4111418

文献信息

• Highly efficient asymmetric construction of novel indolines and tetrahydroquinoline derivatives <i>via</i> aza-Barbier/C–N coupling reaction
  作者：Tao Guo、Bin-Hua Yuan、Wen-Jie Liu

  DOI：10.1039/c7ob02891a

  日期：——

  Highly stereoselective syntheses of chiral indolines and tetrahydroquinolines are achieved by combining the asymmetric Zn-mediated allylation of chiral N-tert-butanesulfinyl imines with efficient intramolecular C–N cross-coupling. Herein, the advantages of such a synthetic strategy are illustrated by the synthesis of indolines and tetrahydroquinolines with quaternary stereocenters and multi-substituted

  手性二氢吲哚和四氢喹啉的高度立体选择性合成是通过将不对称的锌介导的手性N-叔丁亚磺酰亚胺亚胺与有效的分子内C–N交叉偶联相结合而实现的。在本文中，这种合成策略的优点通过合成具有季立体中心的二氢吲哚和四氢喹啉和多取代的1-氧代-1,2,3,4-四氢异喹啉来说明。