acetic acid 3,5-diacetoxy-2-[(9H-fluoren-9-yl-methoxycarbonylamino)-methyl]-6-fluoro-tetrahydro-pyran-4-yl ester | 863997-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: acetic acid 3,5-diacetoxy-2-[(9H-fluoren-9-yl-methoxycarbonylamino)-methyl]-6-fluoro-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4S,5R)-4,5-diacetyloxy-2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-6-fluorooxan-3-yl] acetate
• CAS: 863997-77-7
• 化学式: C₂₇H₂₈FNO₉
• 分子量: 529.519
• InChiKey: DULMXDSVCASIJZ-PPILAZRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  acetic acid 3,5-diacetoxy-2-[(9H-fluoren-9-yl-methoxycarbonylamino)-methyl]-6-fluoro-tetrahydro-pyran-4-yl ester 在 potassium cyanide 、 二氯二茂铪 、 silver perchlorate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 [3,4,5-trihydroxy-6-(2-oxo-2,6,7,7a-tetrahydro-benzofuran-6-yloxy)-tetrahydro-pyran-2-ylmethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  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：

  (6-fluoro-3,4,5-trihydroxy-tetrahydro-pyran-2-yl-methyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 、 乙酸酐 在 吡啶 作用下， 以87%的产率得到acetic acid 3,5-diacetoxy-2-[(9H-fluoren-9-yl-methoxycarbonylamino)-methyl]-6-fluoro-tetrahydro-pyran-4-yl ester
  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.