2,2,2-trichloroethyl N,N-bis[4-(oxan-2-yloxy)butyl]carbamate | 302914-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,2,2-trichloroethyl N,N-bis[4-(oxan-2-yloxy)butyl]carbamate
• CAS: 302914-55-2
• 化学式: C₂₁H₃₆Cl₃NO₆
• 分子量: 504.879
• InChiKey: WKCKXXXZGUVWCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl N,N-bis[4-(oxan-2-yloxy)butyl]carbamate 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 为溶剂， 反应 3.5h， 生成 {4-[4-Methyl-5-oxo-5H-furan-(2E)-ylidene]-butyl}-{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
• 作为产物：
  描述：

  2-(4-氯丁氧基)四氢吡喃 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 19.0h， 生成 2,2,2-trichloroethyl N,N-bis[4-(oxan-2-yloxy)butyl]carbamate
  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