menisdaurilide | 67765-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: menisdaurilide
• 英文别名: (6S,7aR)-6-hydroxy-7,7a-dihydro-6H-1-benzofuran-2-one
• CAS: 67765-59-7
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: RAXNUTINVDSFEU-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  储存条件：2-8°C，密封保存，干燥环境且避光。

制备方法与用途

溶解于二氯甲烷

反应信息

• 作为反应物：
  描述：

  menisdaurilide 在 potassium cyanide 、 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 phyllanthurinolactone
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129
• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 水 、 碘 、 mercury(II) trifluoroacetate 、 sodium hydride 、 溶剂黄146 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 menisdaurilide
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129

文献信息

• Diastereoselective Synthesis of Allosecurinine and Viroallosecurinine from Menisdaurilide
  作者：Gisela G. Bardají、Mariona Cantó、Ramón Alibés、Pau Bayón、Félix Busqué、Pedro de March、Marta Figueredo、Josep Font

  DOI：10.1021/jo801470u

  日期：2008.10.3

  A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.

  据报道，一种新的，通用的合成Securinega生物碱的途径。使用乙烯基类曼尼希反应作为关键转化，从（+）-menisdaurilide开始，以7个步骤和40％的产率完成了Allosecurinine的首次合成。类似地，已经从（-）-半月桂脲内酯合成了四氢阿糖嘌呤。
• Bio‐inspired Total Synthesis of Twelve <i>Securinega</i> Alkaloids: Structural Reassignments of (+)‐Virosine B and (−)‐Episecurinol A
  作者：Kevin Antien、Aitor Lacambra、Fernando P. Cossío、Stéphane Massip、Denis Deffieux、Laurent Pouységu、Philippe A. Peixoto、Stéphane Quideau

  DOI：10.1002/chem.201903122

  日期：2019.9.2

  isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (-)-episecurinol A

  所谓的Securinega生物碱构成了一类四环生物活性的专门代谢产物，主要从竹兰科的亚热带植物中分离出来。遵循基于其生物合成的替代假设的策略后，简单而省时的发散性合成使得能够获得十二种具有（新）（正）紫ur烷骨架的生物碱。此外，这项工作允许重新分配（+）-病毒B和（-）-表肌酐A的绝对构型。
• Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B
  作者：Sanghyeon Lee、Gyumin Kang、Garam Chung、Dongwook Kim、Hee‐Yoon Lee、Sunkyu Han

  DOI：10.1002/anie.201916613

  日期：2020.4.20

  A and B. We demonstrated that the relative stereochemistry at the C2 position of these advanced intermediates governs the fate of 1,2-amine shift leading to fluvirosaones A and B, respectively. While our synthetic design was inspired by the biosynthetic hypothesis of these natural products, syntheses of potential biosynthetic precursors and investigations of their chemical reactivity inversely have

  我们提出了一个简单的合成secu'amamine A，fluvirosaones A和B从容易获得的阿洛斯可宁和virallallosecurinine。这些天然产物的假定的生物合成前体，是（病毒）阿糖嘌呤的关键C2-烯胺衍生物，是通过VO（acac）2介导的区域选择性Polonovski反应首次获得的。该多能烯胺化合物的正式水合和1,2-胺转移提供了secu'amamineA。另一方面，该烯胺与TMS取代的甲基烯丙基碘化物试剂之间的正式氧化[3 + 2]环加成反应为推测的铺平了道路。 fluvirosaones A和B的生物合成前体。我们证明了这些高级中间体的C2位置处的相对立体化学分别控制导致fluvirosaones A和B的1，2-胺转移的命运。
• From p-benzoquinone to cyclohexane chirons: first asymmetric synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide
  作者：Felix Busqué、Mariona Cantó、Pedro de March、Marta Figueredo、Josep Font、Sonia Rodrı́guez

  DOI：10.1016/s0957-4166(03)00357-4

  日期：2003.7

  Starting from a common, easily available, enantiopure monoketal of p-benzoquinone, the synthesis of a large number of cyclohexane chirons has been achieved. The first synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide has been performed from one of these new building blocks. The wide variety of functional groups of this series of chirons makes them useful for subsequent synthetic processes. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Fluorescence study on the nyctinasty of Phyllanthus urinaria L. using novel fluorescence-labeled probe compounds
  作者：Nobuki Kato、Masayoshi Inada、Hirotaka Sato、Ryoji Miyatake、Tsutomu Kumagai、Minoru Ueda

  DOI：10.1016/j.tet.2006.05.022

  日期：2006.7

  We report the synthesis of fluorescence-labeled probes based on phyllanthurinolactone 1, which is a leaf-closing substance of Phyllanthus urinaria L. The fluorescence study using biologically active probe 2 and inactive probes (epi-2 and 31) revealed that the target cell for 1 is a motor cell and suggested that some receptors, which recognize the aglycon of I exist on the plasma membrane of the motor cell, as with leaf-opening substances. Moreover, binding of probe 2 was specific to the plant motor cell contained in the plants belonging to the genus Phyllanthus. These results showed that the binding of probe 2 with a motor cell is specific to the plant genus and suggested that the genus-specific receptor for the leaf-closing substance would be involved in nyctinasty. (c) 2006 Elsevier Ltd. All rights reserved.