(S)-N-[(E,1R)-1-cyclohexa-2,5-dien-1-yl-3-phenylprop-2-enyl]-2-methylpropane-2-sulfinamide | 1023378-05-3

• 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-[(E,1R)-1-cyclohexa-2,5-dien-1-yl-3-phenylprop-2-enyl]-2-methylpropane-2-sulfinamide
• CAS: 1023378-05-3
• 化学式: C₁₉H₂₅NOS
• 分子量: 315.48
• InChiKey: MOLDXKPFOFSJNR-DYDAIYTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  1,4-环己二烯 、 (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide 在 四甲基乙二胺 、 (2-methylpropyl)lithium 、 magnesium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以75%的产率得到(S)-2-methyl-propane-2-sulfinic acid ((E)-(R)-1-(R)-cyclohexa-2,4-dienyl-3-phenylallyl)-amide
  参考文献：
  名称：

  Desymmetrization of Metallated Cyclohexadienes with Chiral N-tert-Butanesulfinyl Imines

  摘要：

  This communication describes the desymmetrization of various achiral metallated cyclohexadienes with a series of chiral N-tert-butanesulfinyl imines. Depending on the metal used, either the symmetrical diene (dicyclohexadienyl-zinc) or the desymmetrized diene (cyclohexadienyl-MgCl) is obtained in a good regioselectivity with excellent diastereoselectivity. The products formed should be useful building blocks for natural product synthesis. The symmetrical 1,4-dienes are readily oxidized to the corresponding diarylmethylamine derivatives.

  DOI：

  10.1021/ol800478q

文献信息

• Desymmetrization of Metallated Cyclohexadienes with Chiral <i>N-tert</i>-Butanesulfinyl Imines
  作者：Modhu Sudan Maji、Roland Fröhlich、Armido Studer

  DOI：10.1021/ol800478q

  日期：2008.5.1

  This communication describes the desymmetrization of various achiral metallated cyclohexadienes with a series of chiral N-tert-butanesulfinyl imines. Depending on the metal used, either the symmetrical diene (dicyclohexadienyl-zinc) or the desymmetrized diene (cyclohexadienyl-MgCl) is obtained in a good regioselectivity with excellent diastereoselectivity. The products formed should be useful building blocks for natural product synthesis. The symmetrical 1,4-dienes are readily oxidized to the corresponding diarylmethylamine derivatives.