norpandamarilactonine-B | 367941-41-1

• 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: norpandamarilactonine-B
• 英文别名: Norpandamarilactonine B；(2S)-4-methyl-2-[(2S)-pyrrolidin-2-yl]-2H-furan-5-one
• CAS: 367941-41-1
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: LJJVKZSKPLBBSU-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E/Z)-5-(4-iodobutylidene)-3-methylfuran-2(5H)-one 、 norpandamarilactonine-B 在 silver carbonate 作用下， 以 乙腈 为溶剂， 以48%的产率得到pandamarilactonine-A
  参考文献：
  名称：

  通过第一步不对称全合成法测定露兜树生物碱，pandamarilactonine-A的绝对构型

  摘要：

  基于从1-脯氨醇开始的全合成，建立了吡咯烷生物碱pandamarilactonine-A的绝对构型。对天然pandamarilactonine-A对映体纯度低的机理的见解进行了讨论。

  DOI：

  10.1016/j.tetlet.2005.06.148
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 三乙基硅烷 、 indium 、 Wilkinson's catalyst 、 碘代三甲硅烷 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 norpandamarilactonine-B
  参考文献：
  名称：

  通过第一步不对称全合成法测定露兜树生物碱，pandamarilactonine-A的绝对构型

  摘要：

  基于从1-脯氨醇开始的全合成，建立了吡咯烷生物碱pandamarilactonine-A的绝对构型。对天然pandamarilactonine-A对映体纯度低的机理的见解进行了讨论。

  DOI：

  10.1016/j.tetlet.2005.06.148

文献信息

• Synthetic Studies onPandanus Alkaloids: From Norpandamarilactonines to Pandamarilactonines, a Proof of Their Configurational Instability
  作者：Pilar Blanco、Felix Busqué、Pedro de March、Marta Figueredo、Josep Font、Elena Sanfeliu

  DOI：10.1002/ejoc.200300474

  日期：2004.1

  The ethyl carbamate of norpandamarilactonine-A was prepared in an enantiomerically pure form starting from (S)-prolinol. Deprotection of the amine functionality rendered both diastereomeric norpandamarilactonines as racemates, which were used as synthetic precursors of pandamarilactonine-A and -B. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  从 (S)-脯氨醇开始，以对映体纯的形式制备去甲潘丹马里内酯-A 的氨基甲酸乙酯。胺官能团的脱保护使非对映异构体去甲熊猫内酯均成为外消旋物，用作熊猫内酯-A和-B的合成前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Total synthesis of four Pandanus alkaloids: pandamarilactonine-A and -B and their chemical precursors norpandamarilactonine-A and -B
  作者：Félix Busqué、Pedro de March、Marta Figueredo、Josep Font、Elena Sanfeliu

  DOI：10.1016/s0040-4039(02)01129-2

  日期：2002.8

  Norpandamarilactonine-A and -B are prepared from (S)-prolinol and converted into pandamarilactonine-A and -B.

  由（S）-脯氨醇制备去甲扁桃酸内酯-A和-B，并将其转化为pandamarilactonine-A和-B。
• Isolation and Structure Elucidation of Two New Alkaloids, Pandamarilactonine-C and -D, from Pandanus amaryllifolius and Revision of Relative Stereochemistry of Pandamarilactonine-A and -B by Total Synthesis.
  作者：Hiromitsu Takayama、Tomotake Ichikawa、Mariko Kitajima、Maribel G. Nonato、Norio Aimi

  DOI：10.1248/cpb.50.1303

  日期：——

  Two new pyrrolidine alkaloids, pandamarilactonine-C and -D, were isolated from Pandanus amaryllifolius. Based on the total synthesis of pandamarilactonine-C and its related alkaloid, pandamarilactonine-A, the relative stereochemistry of pandamarilactonine-A and -B, which was previously proposed by spectroscopic analysis, was revised.

  从露兜树中分离出两种新的吡咯烷生物碱，pandamarilactonine-C和-D。在对pandamarilactonine-C及其相关生物碱pandamarilactonine-A进行全合成的基础上，修订了以前通过光谱分析提出的pandamarilactonine-A和-B的相对立体化学。
• Isolation and Characterization of Two New Alkaloids, Norpandamarilactonine-A and -B, from <i>Pandanus amaryllifolius</i> by Spectroscopic and Synthetic Methods
  作者：Hiromitsu Takayama、Tomotake Ichikawa、Mariko Kitajima、Maribel G. Nonato、Norio Aimi

  DOI：10.1021/np010213h

  日期：2001.9.1

  Two new alkaloids, norpandamarilactonine-A (1) and -B (2), which have a pyrrolidinyl-alpha,beta -unsaturated gamma -lactone moiety as in the known pandamarilactonine alkaloids, were isolated from the leaves of Pandanus amaryllifolius. Their structures were determined by spectroscopic analysis and total synthesis.
• Determination of absolute configuration of Pandanus alkaloid, pandamarilactonine-A, by first asymmetric total synthesis
  作者：Hiromitsu Takayama、Rie Sudo、Mariko Kitajima

  DOI：10.1016/j.tetlet.2005.06.148

  日期：2005.8

  The absolute configuration of pandamarilactonine-A, a pyrrolidine alkaloid, was established on the basis of total synthesis starting from l-prolinol. An insight into the mechanism of the low enantiomeric purity of natural pandamarilactonine-A is discussed.

  基于从1-脯氨醇开始的全合成，建立了吡咯烷生物碱pandamarilactonine-A的绝对构型。对天然pandamarilactonine-A对映体纯度低的机理的见解进行了讨论。

表征谱图