(S_S,S)-(+)-N-(1-isopropyl-1-methyl-hex-2-ynyl)-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_S,S)-(+)-N-(1-isopropyl-1-methyl-hex-2-ynyl)-2-methyl-2-propanesulfinamide
• 英文别名: (S)-N-[(3S)-2,3-dimethyloct-4-yn-3-yl]-2-methylpropane-2-sulfinamide
• 化学式: C₁₄H₂₇NOS
• 分子量: 257.44
• InChiKey: MEPWVFLDUMLDKZ-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S,E)-2-methyl-N-(3-methylbutan-2-ylidene)propane-2-sulfinamide 、 1-戊炔 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71%的产率得到(S_S,S)-(+)-N-(1-isopropyl-1-methyl-hex-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

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.