homopumiliotoxin 235C | 678996-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: homopumiliotoxin 235C
• 英文别名: alkaloid 235C；dehydrohomopumiliotoxin；(5Z)-5-[(9aS)-1-methyl-4,6,7,8,9,9a-hexahydroquinolizin-3-ylidene]pentan-2-ol
• CAS: 678996-74-2
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: AHEJLXVLILVPHL-DVKUMEHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  homopumiliotoxin 235C 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 homopumiliotoxin 233F
  参考文献：
  名称：

  Synthesis of the putative structures of homopumiliotoxins 235C and 233F

  摘要：

  A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.126
• 作为产物：
  描述：

  2-((Z)-4,5-Dibromo-pent-3-enyl)-2-methyl-[1,3]dioxolane 在 盐酸 、 palladium diacetate 、 lithium aluminium tetrahydride 、 三氯化铝 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 homopumiliotoxin 235C
  参考文献：
  名称：

  Synthesis of the putative structures of homopumiliotoxins 235C and 233F

  摘要：

  A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.126

文献信息

• Synthesis of the putative structures of homopumiliotoxins 235C and 233F
  作者：Paul Armstrong、Stephanie Feutren、Helena McAlonan、Gavin O’Mahony、Paul J. Stevenson

  DOI：10.1016/j.tetlet.2003.12.126

  日期：2004.2

  A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.