(S)-(+)-N-(1-cyclohexyl-propylidene)-2-methyl-2-propanesulfinamide

• 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: (S)-(+)-N-(1-cyclohexyl-propylidene)-2-methyl-2-propanesulfinamide
• 英文别名: (NE,S)-N-(1-cyclohexylpropylidene)-2-methylpropane-2-sulfinamide
• 化学式: C₁₃H₂₅NOS
• 分子量: 243.414
• InChiKey: OHQKKGPXLSYIQP-GRNBYLDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-N-(1-cyclohexyl-propylidene)-2-methyl-2-propanesulfinamide 、 三甲基乙炔基硅 在 正丁基锂 、 三甲基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.25h， 以80%的产率得到(S_S,S)-(+)-N-(1-cyclohexyl-1-ethyl-3-(trimethylsilanyl)-prop-2-ynyl)-2-methyl-2-propanesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of α,α-Dibranched Propargylamines by Acetylide Additions to N-tert-Butanesulfinyl Ketimines

  摘要：

  Addition of lithium acetylides prepared from 1-pentyne, phenylacetylene, and trimethylsilylacetylene to diverse N-tert-butanesulfinyl ketimines affords a range of alpha, alpha-dibranched propargyl sulfinamides in generally good yields (up to 87%) and with high diastereoselectivities (up to > 99: 1). Acidic cleavage of the tert-butanesulfinyl group provides the free alpha, alpha-dibranched propargylamines.

  DOI：

  10.1021/jo061160h
• 作为产物：
  描述：

  环己基甲乙酮 、 S-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(S)-(+)-N-(1-cyclohexyl-propylidene)-2-methyl-2-propanesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of α,α-Dibranched Propargylamines by Acetylide Additions to N-tert-Butanesulfinyl Ketimines

  摘要：

  Addition of lithium acetylides prepared from 1-pentyne, phenylacetylene, and trimethylsilylacetylene to diverse N-tert-butanesulfinyl ketimines affords a range of alpha, alpha-dibranched propargyl sulfinamides in generally good yields (up to 87%) and with high diastereoselectivities (up to > 99: 1). Acidic cleavage of the tert-butanesulfinyl group provides the free alpha, alpha-dibranched propargylamines.

  DOI：

  10.1021/jo061160h

文献信息

• Asymmetric Synthesis of α,α-Dibranched Propargylamines by Acetylide Additions to <i>N</i>-<i>tert</i>-Butanesulfinyl Ketimines
  作者：Andrew W. Patterson、Jonathan A. Ellman

  DOI：10.1021/jo061160h

  日期：2006.9.1

  Addition of lithium acetylides prepared from 1-pentyne, phenylacetylene, and trimethylsilylacetylene to diverse N-tert-butanesulfinyl ketimines affords a range of alpha, alpha-dibranched propargyl sulfinamides in generally good yields (up to 87%) and with high diastereoselectivities (up to > 99: 1). Acidic cleavage of the tert-butanesulfinyl group provides the free alpha, alpha-dibranched propargylamines.