3-chloro-2-(furan-2-yl)-1H-pyrrole | 225092-71-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-chloro-2-(furan-2-yl)-1H-pyrrole
• CAS: 225092-71-7
• 化学式: C₈H₆ClNO
• 分子量: 167.595
• InChiKey: JSVNEZIIJXOLKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(furan-2-yl)-1H-pyrrole 在 盐酸 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 3-Chloro-2-{5-[1-pyrrol-(2Z)-ylidene-ethyl]-furan-2-yl}-1-triisopropylsilanyl-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
• 作为产物：
  描述：

  N-(3-chloro-2-propenyl)furan-2-carboxylic acid amide 在 potassium tert-butylate 、 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 16.17h， 生成 3-chloro-2-(furan-2-yl)-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.