4-(3,3-dimethylbut-1-ynyl)-5-neopentyl-3,4-dihydro-2H-pyrrol-4-ol | 1207670-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3,3-dimethylbut-1-ynyl)-5-neopentyl-3,4-dihydro-2H-pyrrol-4-ol
• 英文别名: 4-(3,3-Dimethylbut-1-ynyl)-5-(2,2-dimethylpropyl)-2,3-dihydropyrrol-4-ol
• CAS: 1207670-00-5
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: RWJAHRQAQUTPLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(2-aminoethyl)-2,2,8,8-tetramethylnona-3,6-diyn-5-ol 在 silver(1,10-phenanthroline)OTf 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以80%的产率得到4-(3,3-dimethylbut-1-ynyl)-5-neopentyl-3,4-dihydro-2H-pyrrol-4-ol
  参考文献：
  名称：

  Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I

  摘要：

  An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by H-1 NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I.

  DOI：

  10.1021/jo902674j

文献信息

• Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I
  作者：Vijaya Bhaskara Reddy Iska、Vincenzo Verdolino、Olaf Wiest、Paul Helquist

  DOI：10.1021/jo902674j

  日期：2010.2.19

  An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by H-1 NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I.