aquilegiolide | 94481-79-5

• 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: aquilegiolide
• 英文别名: (6S,7aS)-6-hydroxy-7,7a-dihydro-6H-1-benzofuran-2-one
• CAS: 94481-79-5
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: RAXNUTINVDSFEU-RQJHMYQMSA-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

反应信息

• 作为反应物：
  描述：

  aquilegiolide 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(+/-)-6-oxo-7,7aα-dihydrobenzofuran-2(4H)-one
  参考文献：
  名称：

  Synthesis and absolute configuration of phyllanthurinolactone, the leaf-closing factor of a nyctinastic plant, Phyllanthus urinaria L.

  摘要：

  Phyllanthurinolactone (1) and its diastereoisomer 19 were synthesized, only the former of which was bioactive as the leaf-closing factor of Phyllanthus urinaria L. X-ray analysis of the tetraacetylglucoside 18 was executed, and the absolute configuration of 1 was determined as 6S, 7aR. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02375-1
• 作为产物：
  描述：

  4,5-epoxy-cyclohexene 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 正丁基锂 、 amanolipase AK 、 potassium carbonate 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 97.58h， 生成 aquilegiolide
  参考文献：
  名称：

  Enantioselective total synthesis of virosaine A and bubbialidine

  摘要：

  描述了 virosaine A 和 bubbialidine 的第一个对映选择性全合成。关键转化包括通过分子内氮杂-迈克尔加成形成四环中间体、通过 Cope 消除生成 N-羟基-吡咯烷以及分子内 [1,3]-偶极环加成生成复杂的 7-oxa-1-氮杂双环[3.2.1]辛烷环系。

  DOI：

  10.1039/c3cc38783f

文献信息

• 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.
• Synthesis and absolute configuration of phyllanthurinolactone, the leaf-closing factor of a nyctinastic plant, Phyllanthus urinaria L.
  作者：Kenji Mori、Gérard Audran、Yoshiaki Nakahara、Masahiko Bando、Masaru Kido

  DOI：10.1016/s0040-4039(96)02375-1

  日期：1997.1

  Phyllanthurinolactone (1) and its diastereoisomer 19 were synthesized, only the former of which was bioactive as the leaf-closing factor of Phyllanthus urinaria L. X-ray analysis of the tetraacetylglucoside 18 was executed, and the absolute configuration of 1 was determined as 6S, 7aR. (C) 1997, Elsevier Science Ltd. All rights reserved.
• 10.1002/(sici)1099-0690(199801)1998:1<57::aid-ejoc57<3.0.co;2-w
  作者：Audran, Gerard、Mori, Kenji

  DOI：10.1002/(sici)1099-0690(199801)1998:1<57::aid-ejoc57<3.0.co;2-w

  日期：——
• Enantioselective total synthesis of virosaine A and bubbialidine
  作者：Hideki Miyatake-Ondozabal、Linda M. Bannwart、Karl Gademann

  DOI：10.1039/c3cc38783f

  日期：——

  The first enantioselective total syntheses of virosaine A and bubbialidine are described. Key transformations include the formation of a tetracyclic intermediate via an intramolecular aza-Michael addition, generation of a N-hydroxy-pyrrolidine through a Cope elimination and an intramolecular [1,3]-dipolar cycloaddition to generate a complex 7-oxa-1-azabicyclo[3.2.1]octane ring system.

  描述了 virosaine A 和 bubbialidine 的第一个对映选择性全合成。关键转化包括通过分子内氮杂-迈克尔加成形成四环中间体、通过 Cope 消除生成 N-羟基-吡咯烷以及分子内 [1,3]-偶极环加成生成复杂的 7-oxa-1-氮杂双环[3.2.1]辛烷环系。