(S)-(-)-3-butyl-7-hydroxyphthalide | 649763-00-8

• 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: (S)-(-)-3-butyl-7-hydroxyphthalide
• 英文别名: (-)-3-butyl-7-hydroxyphthalide；3(S)-butyl-7-hydroxyphthalide；CAS No. 649763-00-8；3-butyl-1(3H)-isobenzofuranone；1(3H)-Isobenzofuranone, 3-butyl-7-hydroxy-, (3S)-；(3S)-3-butyl-7-hydroxy-3H-2-benzofuran-1-one
• CAS: 649763-00-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: UWGOKYNWVHSOJQ-JTQLQIEISA-N

物化性质

• 沸点：
  364.0±42.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-3-acetoxy-1-heptyne 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 正丁基锂 、 四丁基氟化铵 、 sodium methylate 、 三氯化硼 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 (S)-(-)-3-butyl-7-hydroxyphthalide
  参考文献：
  名称：

  Chemoenzymatic total synthesis of paecilocin A and 3-butyl-7-hydroxyphthalide

  摘要：

  A highly enantioselective total synthesis of paecilocin A and 3-butyl-7-hydroxyphthalide is described. The key steps involved in this synthesis are enzymatic kinetic resolution and Alder-Rickert reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.089

文献信息

• Synthesis and Absolute Configuration of (−)-3-Butyl-7-hydroxyphthalide, a Cytotoxic Metabolite of<i>Penicillium vulpinum</i>*
  作者：Tomoya OHZEKI、Kenji MORI

  DOI：10.1271/bbb.67.2240

  日期：2003.1

  Both the enantiomers as well as the racemate of 3-butyl-7-hydroxyphthalide (1) were synthesized, and the absolute configuration of the naturally occurring (−)-1 (a weakly cytotoxic metabolite of Penicillium vulpinum) was identified as S.

  合成了 3-丁基-7-羟基苯酞（1）的对映体和外消旋体，并确定了天然存在的 (-)-1（Penicillium vulpinum 的一种弱细胞毒性代谢物）的绝对构型为 S。
• USE OF PHTHALIDE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF DIABETES MELLITUS
  申请人：DSM IP Assets B.V.

  公开号：EP1622605B1

  公开（公告）日：2009-07-15
• Use of phthalide derivatives for the treatment and prevention of diabetes mellitus
  申请人：D'Orazio Daniel

  公开号：US20070082947A1

  公开（公告）日：2007-04-12

  The present invention relates to the use of a compound as effective agent for the prevention or treatment of diabetes mellitus in a mammal. Said compounds being selected from the group of phthalide derivatives and exhibit excellent blood glucose lowering effects and thus are effective agents in the prevention or treatment of diabetes mellitus in mammals.
• NOVEL USE OF ORGANIC COMPOUNDS
  申请人：Fowler Ann

  公开号：US20090176873A1

  公开（公告）日：2009-07-09

  The present invention relates to the use of compounds of the formula (I) wherein the clotted line is an optional bond; R 1 is butyl or butyryl if R 2 is hydroxyl but is butyl if R 2 is hydrogen; or R 1 and R 2 taken together are 1-butylidene optionally substituted by hydroxyl, methyl, or 3-(α,β-dimethylacrylyloxy)-pentylidenyl; X is a residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 is hydroxyl or butyryl; and n is 1 or 2, as agents for the prevention, control and treatment of conditions requiring modulation of inflammation in mammals. In another aspect, the present invention relates to the use of compounds of the formula (I) as active ingredients in the manufacture of medicaments/compositions for the prevention, control and treatment of conditions requiring modulation of inflammation. The compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the management of pain, fever and injuries, especially sport injuries. Moreover, the compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the maintenance and regeneration of articular cartilage.
• ORGANIC COMPOUNDS FOR TREATMENT OF DISORDERS CONNECTED TO IMPAIRED NEUROTRANSMISSION
  申请人：De Saizieu Antoine

  公开号：US20100184852A1

  公开（公告）日：2010-07-22

  The present invention refers to compounds of the general formula (I) wherein R 1 is hydrogen or hydroxy; R 2 is butyl or butyryl if R 1 is hydroxy, but R 2 is butyl if R 1 is hydrogen; or R 3 and R 2 taken together are 1-propylidene or 1-butylidene optionally substituted by hydroxy, methyl, or 3-(α, β-dimethylacryloyloxy); the dotted line is an optional bond; X is an optionally substituted aliphatic C4-residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 and R 4 are, independently from each other, hydrogen or hydroxy; and R 5 is hydroxy or butyryl, for use in the treatment of disorders connected to impaired neurotransmission, as well as to dietary and pharmaceutical compositions containing such compounds, and their uses.