pandanamine | 302914-53-0

• 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: pandanamine
• 英文别名: (5Z)-3-methyl-5-[4-[[(4Z)-4-(4-methyl-5-oxofuran-2-ylidene)butyl]amino]butylidene]furan-2-one
• CAS: 302914-53-0
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: UFHQEIRNGIAWOB-DUGOVBPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pandanamine 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以9%的产率得到(+/-)-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 三甲基氯硅烷 、 草酰氯 、 三氟化硼乙醚 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 9.0h， 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

文献信息

• Synthesis of 6Z-Pandanamine by Regioselective Cyclization Reaction of 2-En-4-ynoic Acid Derivatives Promoted by Weak Base
  作者：Kou Hiroya、Kazuya Takuma、Kiyofumi Inamoto、Takao Sakamoto

  DOI：10.3987/com-08-s(f)48

  日期：——

  The stereoselective synthesis of 6Z-pandanamine by base-promoted 5-exo-dig-selective cyclization reaction of bis-2-en-4-ynoic acid derivative as a key step is described

  以碱促进的5-exo-dig-bis-2-en-4-ynoic酸衍生物的选择性环化反应为关键步骤立体选择性合成6Z-pandanamine
• Synthesis of Norpandamarilactonines, Pandamarilactonines, and ­Pandanamine
  作者：Narshinha Argade、Sanjib Gogoi

  DOI：10.1055/s-2008-1072534

  日期：2008.5

  A facile route to naturally occurring (±)-norpandamarilactonines A and B, (±)-pandamarilactonines A-D, and pandanamine has been described from 3-methylfuran-2(5H)-one, with a reductive intramolecular aza-Michael-type addition as the key step.

  已经描述了一条简单的路线，从3-甲基呋喃-2(5H)-酮合成天然存在的(±)-诺潘达玛里内A和B、(±)-潘达玛里内A-D以及潘达敏，该关键步骤为还原性分子内氮杂迈克尔加成反应。
• 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.

表征谱图