pandamarilactonine

• 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: pandamarilactonine
• 英文别名: pandamarilactonine-A；3-methyl-5-[4-[2-(4-methyl-5-oxo-2H-furan-2-yl)pyrrolidin-1-yl]butylidene]furan-2-one
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: HSICZNIIIPFAAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pandamarilactonine 在 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以63%的产率得到pandanamine
  参考文献：
  名称：

  Synthesis of Norpandamarilactonines, Pandamarilactonines, and ­Pandanamine

  摘要：

  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。

  DOI：

  10.1055/s-2008-1072534
• 作为产物：
  描述：

  pandanamine 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以9 mg的产率得到pandamarilactonine
  参考文献：
  名称：

  New Alkaloids from Pandanus amaryllifolius

  摘要：

  Three new alkaloids, the two pyrrolidine type alkaloids (1 and 2) and 6E-pandanamine (3), together with five known alkaloids (4-8), were isolated from the leaves of Pandanus amaryllifolius collected in West Java, Indonesia. All the new alkaloids have two alpha-methyl alpha,beta-unsaturated gamma-lactone moieties, while compound 2 also has an additional seven-membered ring, which has not been encountered before in Pandanus alkaloids. Two different extraction methods, namely, a solvent partitioning extraction and acid-base treatment, were tested, giving secondary and tertiary amines, respectively. Spectroscopic and chemical studies showed that the tertiary amines isolated from the acid-base treatment were artifacts formed during the extraction process. This finding suggests that the use of conventional acid-base treatment in isolating Pandanus alkaloids should be reviewed since it can introduce artifacts.

  DOI：

  10.1021/np0303310

文献信息

• Synthesis of Pandamarilactone-1
  作者：Kang Yee Seah、Sarah J. Macnaughton、Jonathan W. P. Dallimore、Jeremy Robertson

  DOI：10.1021/ol4036424

  日期：2014.2.7

  The first total synthesis of pandamarilactone-1, an alkaloid of Pandanus amaryllifolius, is reported. The nine-step synthesis features furan oxidation with singlet oxygen and then spiro-N,O-acetalization and elimination to generate the natural product and further Pandanus alkaloids, pandamarilactonines A–D.

  首次全合成了露兜树的一种生物碱pandamarilactone-1 。九步合成的特点是用单线态氧氧化呋喃，然后螺-N,O-缩醛化和消除，生成天然产物和进一步的露兜树生物碱，熊猫内酯 A-D。
• Diastereoselective Synthesis of<i>N</i>-Boc-Norpandamarilactonine-B and Pandamarilactonine-A
  作者：Toshio Honda、Misugi Katoh、Makoto Ushiwata、Hiroki Shigehisa

  DOI：10.1002/ardp.200700218

  日期：2008.9

  Optically pure N‐Boc‐norpandamarilactonine‐B was diastereoselectively synthesized starting from L‐serine by employing a double ring closing metathesis (RCM) of a tetraene derivative as a key reaction. N‐Boc‐norpandamarilactonine‐B obtained was further converted to pandamarilactonine‐A.

  通过采用四烯衍生物的双闭环复分解（RCM）作为关键反应，以 L-丝氨酸为原料，非对映选择性地合成了光学纯的 N-Boc-norpandamarilactonine-B。得到的 N-Boc-去甲熊猫内酯-B进一步转化为熊猫内酯-A。
• 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。
• New Alkaloids from<i> Pandanus </i><i>a</i><i>maryllifolius</i>
  作者：Angela A. Salim、Mary J. Garson、David J. Craik

  DOI：10.1021/np0303310

  日期：2004.1.1

  Three new alkaloids, the two pyrrolidine type alkaloids (1 and 2) and 6E-pandanamine (3), together with five known alkaloids (4-8), were isolated from the leaves of Pandanus amaryllifolius collected in West Java, Indonesia. All the new alkaloids have two alpha-methyl alpha,beta-unsaturated gamma-lactone moieties, while compound 2 also has an additional seven-membered ring, which has not been encountered before in Pandanus alkaloids. Two different extraction methods, namely, a solvent partitioning extraction and acid-base treatment, were tested, giving secondary and tertiary amines, respectively. Spectroscopic and chemical studies showed that the tertiary amines isolated from the acid-base treatment were artifacts formed during the extraction process. This finding suggests that the use of conventional acid-base treatment in isolating Pandanus alkaloids should be reviewed since it can introduce artifacts.