5-indan-2-ylmethyl-tert-butylsulfinamide | 398490-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-indan-2-ylmethyl-tert-butylsulfinamide
• 英文别名: (NE,R)-N-[2-(2,3-dihydro-1H-inden-2-yl)ethylidene]-2-methylpropane-2-sulfinamide
• CAS: 398490-72-7
• 化学式: C₁₅H₂₁NOS
• 分子量: 263.404
• InChiKey: MEQWKJAXUWYTBK-QJKHOBJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  5-indan-2-ylmethyl-tert-butylsulfinamide 在 dimethyl sulfide borane 、 yttrium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.42h， 生成 (S)-3-Indan-2-yl-propane-1,2-diamine; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  Synthesis of enantiomerically pure ethylenediamines from chiral sulfinimines: a new twist to the Strecker reaction

  摘要：

  Addition of various cyanide nucleophiles on chiral t-butylsulfinimine and p-tolylsulfinimine derivatives are described and demonstrated that aliphatic t-butylsulfinimines are excellent substrates for a new variant of the Strecker reaction where cyanide ions are delivered through ethylisopropoxyaluminum cyanide or trimethylsilylcyanide combined with a Lewis acid catalyst. The reaction proceeds with high yield and high diastereoselectivity, which can be further improved by additional crystallizations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00886-9
• 作为产物：
  描述：

  (R)-(+)-叔丁基亚磺酰胺 、 (indan-2-yl)acetaldehyde 在 4-甲基苯磺酸吡啶 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到5-indan-2-ylmethyl-tert-butylsulfinamide
  参考文献：
  名称：

  Synthesis of enantiomerically pure ethylenediamines from chiral sulfinimines: a new twist to the Strecker reaction

  摘要：

  Addition of various cyanide nucleophiles on chiral t-butylsulfinimine and p-tolylsulfinimine derivatives are described and demonstrated that aliphatic t-butylsulfinimines are excellent substrates for a new variant of the Strecker reaction where cyanide ions are delivered through ethylisopropoxyaluminum cyanide or trimethylsilylcyanide combined with a Lewis acid catalyst. The reaction proceeds with high yield and high diastereoselectivity, which can be further improved by additional crystallizations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00886-9

文献信息

• Synthesis of enantiomerically pure ethylenediamines from chiral sulfinimines: a new twist to the Strecker reaction
  作者：Stéphane Mabic、Alex A. Cordi

  DOI：10.1016/s0040-4020(01)00886-9

  日期：2001.10

  Addition of various cyanide nucleophiles on chiral t-butylsulfinimine and p-tolylsulfinimine derivatives are described and demonstrated that aliphatic t-butylsulfinimines are excellent substrates for a new variant of the Strecker reaction where cyanide ions are delivered through ethylisopropoxyaluminum cyanide or trimethylsilylcyanide combined with a Lewis acid catalyst. The reaction proceeds with high yield and high diastereoselectivity, which can be further improved by additional crystallizations. (C) 2001 Elsevier Science Ltd. All rights reserved.