2-(furan-2-yl)-1-triisopropyl-1H-pyrrole | 225092-67-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(furan-2-yl)-1-triisopropyl-1H-pyrrole
• 英文别名: [2-(Furan-2-yl)pyrrol-1-yl]-tri(propan-2-yl)silane
• CAS: 225092-67-1
• 化学式: C₁₇H₂₇NOSi
• 分子量: 289.493
• InChiKey: JOMNLFAMEONBFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(furan-2-yl)-1-triisopropyl-1H-pyrrole 在 盐酸 作用下， 反应 0.08h， 生成
  参考文献：
  名称：

  A Second Generation Synthesis of Roseophilin and Chromophore Analogues

  摘要：

  A concise, flexible, and high-yielding synthesis of the macrocyclic compound 4 is outlined which served as a key intermediate in a previous total synthesis of the antitumor active alkaloid roseophilin 1. The key steps of this approach consist of a Pd(0)-catalyzed reaction of vinyloxirane 6 with sulfone 7 and in a subsequent ring closing metathesis (RCM) reaction for the formation of the 13-membered ring catalyzed by the ruthenium carbene Cl-2(PCy3)(2)Ru=CHCH=CPh2 introduced by Grubbs. Moreover, nitrile ylide cycloaddition reactions are used for the preparation of roseophilin side chain mimics. Finally, the synthesis of various chromophore analogues of 1 is reported, including deschloro-desmethoxyroseophilin 12 which is the most elaborate derivative of this complex target reported so far.

  DOI：

  10.1021/jo982088t
• 作为产物：
  描述：

  N-烯丙基-2-糠酰胺 在 potassium tert-butylate 、 potassium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.42h， 生成 2-(furan-2-yl)-1-triisopropyl-1H-pyrrole
  参考文献：
  名称：

  A Second Generation Synthesis of Roseophilin and Chromophore Analogues

  摘要：

  A concise, flexible, and high-yielding synthesis of the macrocyclic compound 4 is outlined which served as a key intermediate in a previous total synthesis of the antitumor active alkaloid roseophilin 1. The key steps of this approach consist of a Pd(0)-catalyzed reaction of vinyloxirane 6 with sulfone 7 and in a subsequent ring closing metathesis (RCM) reaction for the formation of the 13-membered ring catalyzed by the ruthenium carbene Cl-2(PCy3)(2)Ru=CHCH=CPh2 introduced by Grubbs. Moreover, nitrile ylide cycloaddition reactions are used for the preparation of roseophilin side chain mimics. Finally, the synthesis of various chromophore analogues of 1 is reported, including deschloro-desmethoxyroseophilin 12 which is the most elaborate derivative of this complex target reported so far.

  DOI：

  10.1021/jo982088t

文献信息

• A Second Generation Synthesis of Roseophilin and Chromophore Analogues
  作者：Alois Fürstner、Thomas Gastner、Holger Weintritt

  DOI：10.1021/jo982088t

  日期：1999.4.1

  A concise, flexible, and high-yielding synthesis of the macrocyclic compound 4 is outlined which served as a key intermediate in a previous total synthesis of the antitumor active alkaloid roseophilin 1. The key steps of this approach consist of a Pd(0)-catalyzed reaction of vinyloxirane 6 with sulfone 7 and in a subsequent ring closing metathesis (RCM) reaction for the formation of the 13-membered ring catalyzed by the ruthenium carbene Cl-2(PCy3)(2)Ru=CHCH=CPh2 introduced by Grubbs. Moreover, nitrile ylide cycloaddition reactions are used for the preparation of roseophilin side chain mimics. Finally, the synthesis of various chromophore analogues of 1 is reported, including deschloro-desmethoxyroseophilin 12 which is the most elaborate derivative of this complex target reported so far.