(4R,6R)-2-Dihydromenisdaurilide | 150044-54-5

• 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: (4R,6R)-2-Dihydromenisdaurilide
• 英文别名: (6R,7aR)-6-hydroxy-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one
• CAS: 150044-54-5
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: HVKUASSSTFDQDK-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：
  0.62
• 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：

  (4R,6R)-2-Dihydromenisdaurilide 在 potassium cyanide 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 [3,4,5-trihydroxy-6-(2-oxo-2,4,5,6,7,7a-hexahydro-benzofuran-6-yloxy)-tetrahydro-pyran-2-ylmethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Fluorescence study on the nyctinasty of Phyllanthus urinaria L. using novel fluorescence-labeled probe compounds

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.05.022
• 作为产物：
  描述：

  (S)-6-Hydroxy-7,7a-dihydro-6H-benzofuran-2-one 在 Lindlar's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以68%的产率得到(4R,6R)-2-Dihydromenisdaurilide
  参考文献：
  名称：

  Fluorescence study on the nyctinasty of Phyllanthus urinaria L. using novel fluorescence-labeled probe compounds

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.05.022

文献信息

• Cyclohexyl butenolide glucosides from epacridaceae
  作者：Søren Damtoft、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(95)00181-6

  日期：1995.9

  Abstract Trochocarpa laurina contained a new cyclohexyl butenolide glucoside, trochocarposide ( (4S,6R)-2,3-dihydro -4-O-β- d -glucopyranosyl-aquilegiolide ) addition to the iridoid glucoside schismoside. Epacris impressa contained 4-epitrochocarposide ( (4R,6R)-2,3-dihydro -4-O-β- d -glucopyranosyl-menisdaurilide ) which is also a new compound.

  摘要 Trochocarpa laurina 含有一种新的环己基丁烯内酯葡萄糖苷，trochocarposide ( (4S,6R)-2,3-dihydro -4-O-β-d-glucopyranosyl-aquilegiolide ) 除了环烯醚萜苷二裂甙。Epacris impressa 含有 4-epitrochocarposide ( (4R,6R)-2,3-dihydro -4-O-β-d -glupyranosyl-menisdaurilide )，它也是一种新化合物。
• 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.