(-)-(3aS,7aR)-3a,4,7,7a-tetrahydrobenzofuran-2(3H)-one | 124094-65-1

• 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: (-)-(3aS,7aR)-3a,4,7,7a-tetrahydrobenzofuran-2(3H)-one
• 英文别名: (3aS,7aR)-3a,4,7,7a-tetrahydro-3H-1-benzofuran-2-one
• CAS: 124094-65-1
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: PPASVOQVTFYTSL-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(3aS,7aR)-3a,4,7,7a-tetrahydrobenzofuran-2(3H)-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 生成 (+)-(3aS,7aR)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one
  参考文献：
  名称：

  Kosugi, Hiroshi; Tagami, Katsuya; Takahashi, Akira, Journal of the Chemical Society. Perkin transactions I, 1989, p. 935 - 943

  摘要：

  DOI：
• 作为产物：
  描述：

  rel-(1R,6S)-6-Hydroxy-3-cyclohexene-1-acetonitrile 在 sodium hydroxide 、 calcium sulfate 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 以86%的产率得到(-)-(3aS,7aR)-3a,4,7,7a-tetrahydrobenzofuran-2(3H)-one
  参考文献：
  名称：

  Enantio-differential approach using fluorescence-labeled phyllanthurinolactone, a leaf-closing factor of Phyllanthus urinaria L.

  摘要：

  We report here the synthesis of enantio-pair-type fluorescence-labeled probes based on phyllanthurinolactone (1), which is a leaf-closing substance of Phyllanthus urinaria L. Moreover, the application of an enantio-differential approach to distinguish between specific and nonspecific binding of ligands and receptors was performed. Fluorescence studies using a natural-type probe 6 and a nonnatural-type probe 7 revealed that the target cell for I is a motor cell. Furthermore, our results lead to the suggestion that some receptors, which recognize the stereochemistry of the aglycon of 1, exist on the plasma membrane of the motor cell, as do leaf opening substances. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.08.058

文献信息

• MARSHALL J. A.; ELLISON R. H., J. ORG. CHEM. <JOCE-AH>, 1975, 40, NO 14, 2070-2073
  作者：MARSHALL J. A.、 ELLISON R. H.

  DOI：——

  日期：——
• Kosugi, Hiroshi; Tagami, Katsuya; Takahashi, Akira, Journal of the Chemical Society. Perkin transactions I, 1989, p. 935 - 943
  作者：Kosugi, Hiroshi、Tagami, Katsuya、Takahashi, Akira、Kanna, Hiroshi、Uda, Hisashi

  DOI：——

  日期：——
• Enantio-differential approach using fluorescence-labeled phyllanthurinolactone, a leaf-closing factor of Phyllanthus urinaria L.
  作者：Nobuki Kato、Masayoshi Inada、Hirotaka Sato、Satoko Ito、Mitsuru Shoji、Minoru Ueda

  DOI：10.1016/j.tetlet.2007.08.058

  日期：2007.10

  We report here the synthesis of enantio-pair-type fluorescence-labeled probes based on phyllanthurinolactone (1), which is a leaf-closing substance of Phyllanthus urinaria L. Moreover, the application of an enantio-differential approach to distinguish between specific and nonspecific binding of ligands and receptors was performed. Fluorescence studies using a natural-type probe 6 and a nonnatural-type probe 7 revealed that the target cell for I is a motor cell. Furthermore, our results lead to the suggestion that some receptors, which recognize the stereochemistry of the aglycon of 1, exist on the plasma membrane of the motor cell, as do leaf opening substances. (C) 2007 Published by Elsevier Ltd.