1-[2-(5-chloro-1H-indol-3-yl)ethyl]urea | 724441-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[2-(5-chloro-1H-indol-3-yl)ethyl]urea
• 英文别名: 2-(5-chloro-1H-indol-3-yl)ethylurea
• CAS: 724441-13-8
• 化学式: C₁₁H₁₂ClN₃O
• 分子量: 237.689
• InChiKey: ULYQLSIPXPOOOX-UHFFFAOYSA-N

物化性质

• 沸点：
  465.4±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[2-(5-chloro-1H-indol-3-yl)ethyl]urea 、 丁烯酮 在 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以68%的产率得到
  参考文献：
  名称：

  Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

  摘要：

  A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis Is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.

  DOI：

  10.1021/ol401039h
• 作为产物：
  描述：

  potassium cyanate 、 5-氯靛胺盐酸盐 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 以49%的产率得到1-[2-(5-chloro-1H-indol-3-yl)ethyl]urea
  参考文献：
  名称：

  Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

  摘要：

  A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis Is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.

  DOI：

  10.1021/ol401039h

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：NOVACTA BIOSYSTEMS LTD

  公开号：WO2012020222A1

  公开（公告）日：2012-02-16

  Described is a compound of formula (I): wherein X represents a bond or an amino acid residue; R3 represents H or C1-6 alkyl; R4 represents -RA-L-Ar1, or R3 together with R4 and the nitrogen to which they are attached form a 5 or 6 membered heterocyclic group optionally including a further heteroatom selected from N, O or S, wherein said heterocyclic group is substituted by a specified group, and where Z, R1, R2, R5, RA, L and Ar1 are further defined.
• Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
  作者：Isabelle Aillaud、David M. Barber、Amber L. Thompson、Darren J. Dixon

  DOI：10.1021/ol401039h

  日期：2013.6.21

  A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis Is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.