Bis-{4-[4-methyl-5-oxo-5H-furan-(2Z)-ylidene]-butyl}-carbamic acid 2,2,2-trichloro-ethyl ester | 302914-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: Bis-{4-[4-methyl-5-oxo-5H-furan-(2Z)-ylidene]-butyl}-carbamic acid 2,2,2-trichloro-ethyl ester
• 英文别名: 2,2,2-trichloroethyl N,N-bis[(4Z)-4-(4-methyl-5-oxofuran-2-ylidene)butyl]carbamate
• CAS: 302914-60-9
• 化学式: C₂₁H₂₄Cl₃NO₆
• 分子量: 492.784
• InChiKey: AKPNVBDIYBVRDE-DNRQYRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Bis-{4-[4-methyl-5-oxo-5H-furan-(2Z)-ylidene]-butyl}-carbamic acid 2,2,2-trichloro-ethyl ester 在 溶剂黄146 、 锌 作用下， 反应 4.0h， 生成 pandanamine
  参考文献：
  名称：

  Structure Characterization, Biomimetic Total Synthesis, and Optical Purity of Two New Pyrrolidine Alkaloids, Pandamarilactonine-A and -B, Isolated from Pandanus amaryllifolius Roxb.

  摘要：

  Two new alkaloids, both possessing a pyrrolidinyl alpha,beta-unsaturated gamma-lactone residue and a gamma-alkylidene alpha,beta-unsaturated gamma-lactone residue, were isolated from a tropical medicinal plant, Pandanus amaryllifolius Roxb. Their structures were deduced by spectroscopic analysis including the new NMR technique PFG J-HMBC 2D spectroscopy and then confirmed by biomimetic total synthesis. It was found that one diastereoisomer, pandamarilactonine-A (1), comprised a mixture enriched with (+)-enantiomer, while another diastereomeric isomer, pandamarilactonine-B (2), occurred as a racemate.

  DOI：

  10.1021/ja0009929
• 作为产物：
  描述：

  N-benzyl-4-(oxan-2-yloxy)-N-[4-(oxan-2-yloxy)butyl]butan-1-amine 在 三甲基氯硅烷 、 草酰氯 、 三氟化硼乙醚 、 对甲苯磺酸 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 5.0h， 生成 Bis-{4-[4-methyl-5-oxo-5H-furan-(2Z)-ylidene]-butyl}-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Structure Characterization, Biomimetic Total Synthesis, and Optical Purity of Two New Pyrrolidine Alkaloids, Pandamarilactonine-A and -B, Isolated from Pandanus amaryllifolius Roxb.

  摘要：

  Two new alkaloids, both possessing a pyrrolidinyl alpha,beta-unsaturated gamma-lactone residue and a gamma-alkylidene alpha,beta-unsaturated gamma-lactone residue, were isolated from a tropical medicinal plant, Pandanus amaryllifolius Roxb. Their structures were deduced by spectroscopic analysis including the new NMR technique PFG J-HMBC 2D spectroscopy and then confirmed by biomimetic total synthesis. It was found that one diastereoisomer, pandamarilactonine-A (1), comprised a mixture enriched with (+)-enantiomer, while another diastereomeric isomer, pandamarilactonine-B (2), occurred as a racemate.

  DOI：

  10.1021/ja0009929

文献信息

• Structure Characterization, Biomimetic Total Synthesis, and Optical Purity of Two New Pyrrolidine Alkaloids, Pandamarilactonine-A and -B, Isolated from <i>Pandanus amaryllifolius</i> Roxb.
  作者：Hiromitsu Takayama、Tomotake Ichikawa、Toshiyuki Kuwajima、Mariko Kitajima、Hiroko Seki、Norio Aimi、Maribel G. Nonato

  DOI：10.1021/ja0009929

  日期：2000.9.1

  Two new alkaloids, both possessing a pyrrolidinyl alpha,beta-unsaturated gamma-lactone residue and a gamma-alkylidene alpha,beta-unsaturated gamma-lactone residue, were isolated from a tropical medicinal plant, Pandanus amaryllifolius Roxb. Their structures were deduced by spectroscopic analysis including the new NMR technique PFG J-HMBC 2D spectroscopy and then confirmed by biomimetic total synthesis. It was found that one diastereoisomer, pandamarilactonine-A (1), comprised a mixture enriched with (+)-enantiomer, while another diastereomeric isomer, pandamarilactonine-B (2), occurred as a racemate.