6-(4-methoxy-benzyloxy)-7,7a-dihydro-6H-benzofuran-2-one | 863997-73-3

• 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: 6-(4-methoxy-benzyloxy)-7,7a-dihydro-6H-benzofuran-2-one
• 英文别名: (6S)-6-[(4-methoxyphenyl)methoxy]-7,7a-dihydro-6H-1-benzofuran-2-one
• CAS: 863997-73-3
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: KHCAFEYSFQGAGT-GICMACPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-methoxy-benzyloxy)-7,7a-dihydro-6H-benzofuran-2-one 在 哌啶 、 potassium cyanide 、 二氯二茂铪 、 silver perchlorate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6-[2-(7-Amino-4-methyl-2-oxo-2H-chromen-3-yl)-acetylamino]-hexanoic acid [(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((6S,7aR)-2-oxo-2,6,7,7a-tetrahydro-benzofuran-6-yloxy)-tetrahydro-pyran-2-ylmethyl]-amide
  参考文献：
  名称：

  Direct observation of a target cell of the leaf-closing factor by using novel fluorescence-labeled phyllanthurinolactone

  摘要：

  We report the synthesis of the fluorescence-labeled probe 2 based on phyllanthurinolactone 1, which is a leaf-closing substance of Phyllanthus urinaria L. Bioorganic studies using probe 2 showed leaf-closing activity at 1 X 10(-5) M, which was one-hundredth of that of the natural product 1. The fluorescence study using 2 revealed that the target cell for I is a motor cell and suggested that some receptors for 1 exist on the plasma membrane of the motor cell as with leaf-opening substances. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.044
• 作为产物：
  描述：

  tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane 在 potassium tert-butylate 、 四丁基氟化铵 、 mercury(II) trifluoroacetate 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 生成 6-(4-methoxy-benzyloxy)-7,7a-dihydro-6H-benzofuran-2-one
  参考文献：
  名称：

  Direct observation of a target cell of the leaf-closing factor by using novel fluorescence-labeled phyllanthurinolactone

  摘要：

  We report the synthesis of the fluorescence-labeled probe 2 based on phyllanthurinolactone 1, which is a leaf-closing substance of Phyllanthus urinaria L. Bioorganic studies using probe 2 showed leaf-closing activity at 1 X 10(-5) M, which was one-hundredth of that of the natural product 1. The fluorescence study using 2 revealed that the target cell for I is a motor cell and suggested that some receptors for 1 exist on the plasma membrane of the motor cell as with leaf-opening substances. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.044

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.