Bis-(4-oxo-butyl)-carbamic acid 2,2,2-trichloro-ethyl ester | 302914-57-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Bis-(4-oxo-butyl)-carbamic acid 2,2,2-trichloro-ethyl ester
• 英文别名: 2,2,2-trichloroethyl N,N-bis(4-oxobutyl)carbamate
• CAS: 302914-57-4
• 化学式: C₁₁H₁₆Cl₃NO₄
• 分子量: 332.611
• InChiKey: HPOPYHWVCCEJRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Bis-(4-oxo-butyl)-carbamic acid 2,2,2-trichloro-ethyl ester 在 三甲基氯硅烷 、 三氟化硼乙醚 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 、 锌 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 11.0h， 生成 (+/-)-pandamarilactonine-A
  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 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 Bis-(4-oxo-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.