(E)-N-propargyl-1-methyl-5-phenylpent-4-enylamine | 528878-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-propargyl-1-methyl-5-phenylpent-4-enylamine
• 英文别名: (E)-6-phenyl-N-prop-2-ynylhex-5-en-2-amine
• CAS: 528878-13-9
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: SLEASPCRRYBIET-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-propargyl-1-methyl-5-phenylpent-4-enylamine 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 7.5h， 生成 2-chloromethylene-5-methyl-1-phenylpyrrolizidine
  参考文献：
  名称：

  Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

  摘要：

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01613-7
• 作为产物：
  描述：

  反-6-苯基己-5-烯-2-酮 、 炔丙胺 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(E)-N-propargyl-1-methyl-5-phenylpent-4-enylamine
  参考文献：
  名称：

  Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

  摘要：

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01613-7

文献信息

• Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals
  作者：Hikaru Hasegawa、Hisanori Senboku、Yoshinori Kajizuka、Kazuhiko Orito、Masao Tokuda

  DOI：10.1016/s0040-4020(02)01613-7

  日期：2003.2

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.