(Z)-1-but-3-enyl-5-(5-ethylthiophen-2-yl)pent-4-enylamine | 1246269-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (Z)-1-but-3-enyl-5-(5-ethylthiophen-2-yl)pent-4-enylamine
• 英文别名: (1Z)-1-(5-ethylthiophen-2-yl)nona-1,8-dien-5-amine
• CAS: 1246269-66-8
• 化学式: C₁₅H₂₃NS
• 分子量: 249.42
• InChiKey: YCVOYVWCQVXZIN-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-but-3-enyl-5-(5-ethylthiophen-2-yl)pent-4-enylamine 在 1,3-bis(2-iPrC₆H₄)-2-bis(TMS)N-2,1,3-scandiadiazolidine 作用下， 以 氘代甲苯 为溶剂， 反应 12.0h， 生成 (2R,5R)-2-[(Z)-4-(5-ethylthiophen-2-yl)but-3-enyl]-5-methylpyrrolidine
  参考文献：
  名称：

  A Stereocontrolled Synthesis of (±)-Xenovenine via a Scandium(III)-Catalyzed Internal Aminodiene Bicyclization Terminated by a 2-(5-Ethyl-2-thienyl)ethenyl Group

  摘要：

  A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (+/-)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.

  DOI：

  10.1021/ol101646t
• 作为产物：
  描述：

  (Z)-1-(5-ethylthiophen-2-yl)nona-1,8-dien-5-one 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到(Z)-1-but-3-enyl-5-(5-ethylthiophen-2-yl)pent-4-enylamine
  参考文献：
  名称：

  A Stereocontrolled Synthesis of (±)-Xenovenine via a Scandium(III)-Catalyzed Internal Aminodiene Bicyclization Terminated by a 2-(5-Ethyl-2-thienyl)ethenyl Group

  摘要：

  A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (+/-)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.

  DOI：

  10.1021/ol101646t

文献信息

• A Stereocontrolled Synthesis of (±)-Xenovenine via a Scandium(III)-Catalyzed Internal Aminodiene Bicyclization Terminated by a 2-(5-Ethyl-2-thienyl)ethenyl Group
  作者：Tao Jiang、Tom Livinghouse

  DOI：10.1021/ol101646t

  日期：2010.10.1

  A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (+/-)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.