3-(2-Furanyl)butyric acid | 169892-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(2-Furanyl)butyric acid
• 英文别名: 3-(Furan-2-yl)butanoic acid
• CAS: 169892-41-5
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: OAYKXVOHCCDXHA-UHFFFAOYSA-N

物化性质

• 沸点：
  218.4±15.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-Furanyl)butyric acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到3-(2-Furanyl)butan-1-ol
  参考文献：
  名称：

  Intramolecular [4+3] Cycloadditions. Studies of Relative Asymmetric Induction

  摘要：

  Treatment df both the E and Z isomers of alkoxyallylic sulfones 20a and 20b with TiCl4 results in the formation of 4 + 3 cycloadducts by intramolecular cycloaddition. The distribution of diastereomers is different from each isomer of educt. This suggests that cycloaddition occurs faster than any isomerization process of the intermediate allylic cations. Both the E and Z isomers of 20c lead to the same 4 + 3 cycloadduct with essentially complete diastereoselectivity. Inherently high simple diastereoselection and a strong conformational bias in the allylic cation intermediates for both isomers account for this selectivity. The importance of allylic cation stereochemistry in these reactions is underscored by the cyclization of 20d. The Z isomer give only 4 + 3 cycloadducts with excellent relative but poor simple diastereoselection, suggestive of a concerted reaction. The E isomer give a [3 + 2] cycloadduct, enol ether 60, as the major cycloadduct as well as 4 + 3 cycloadducts and chloride-trapping product 61. This result is indicative of a stepwise reaction. The data reflect the importance of allylic cation stereochemistry in the regiochemical and stereochemical outcomes of intramolecular 4 + 3 cycloaddition reactions.

  DOI：

  10.1021/jo00121a028
• 作为产物：
  描述：

  2-乙酰基呋喃 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium hydride 作用下， 以 苯 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 15.5h， 生成 3-(2-Furanyl)butyric acid
  参考文献：
  名称：

  Intramolecular [4+3] Cycloadditions. Studies of Relative Asymmetric Induction

  摘要：

  Treatment df both the E and Z isomers of alkoxyallylic sulfones 20a and 20b with TiCl4 results in the formation of 4 + 3 cycloadducts by intramolecular cycloaddition. The distribution of diastereomers is different from each isomer of educt. This suggests that cycloaddition occurs faster than any isomerization process of the intermediate allylic cations. Both the E and Z isomers of 20c lead to the same 4 + 3 cycloadduct with essentially complete diastereoselectivity. Inherently high simple diastereoselection and a strong conformational bias in the allylic cation intermediates for both isomers account for this selectivity. The importance of allylic cation stereochemistry in these reactions is underscored by the cyclization of 20d. The Z isomer give only 4 + 3 cycloadducts with excellent relative but poor simple diastereoselection, suggestive of a concerted reaction. The E isomer give a [3 + 2] cycloadduct, enol ether 60, as the major cycloadduct as well as 4 + 3 cycloadducts and chloride-trapping product 61. This result is indicative of a stepwise reaction. The data reflect the importance of allylic cation stereochemistry in the regiochemical and stereochemical outcomes of intramolecular 4 + 3 cycloaddition reactions.

  DOI：

  10.1021/jo00121a028

文献信息

• TETRAHYDROBENZOTHIOPHENE DERIVATIVES
  申请人：Bartels Bjorn

  公开号：US20110044938A1

  公开（公告）日：2011-02-24

  Compounds of a certain formula I, in which Ra and Rb have the meanings indicated in the description, are novel effective compounds with anti-proliferative and apoptosis inducing activity.

  某一公式I的化合物，其中Ra和Rb具有说明中所示的含义，是一种新颖的有效化合物，具有抗增殖和诱导凋亡活性。
• NOVEL TETRAHYDROPYRIDOTHIOPHENES
  申请人：Pekari Klaus

  公开号：US20100285149A1

  公开（公告）日：2010-11-11

  Compounds of a certain formula I, in which Ra and Rb have the meanings indicated in the description, are novel effective compounds with anti-proliferative and apoptosis inducing activity.

  某种化学式为I的化合物，其中Ra和Rb具有说明中所示的含义，是具有抗增殖和诱导细胞凋亡活性的新型有效化合物。
• 3-CARBAMOYL-2-PYRIDONE DERIVATIVES
  申请人：ISHIZUKA Natsuki

  公开号：US20120208813A1

  公开（公告）日：2012-08-16

  The present invention provides compounds having an agonistic activity to the cannabinoid receptor, which is represented by the formula (I): wherein R 1 , R 2 , R 3 , R 4 , and G are defined as herein, a pharmaceutically acceptable salt or a solvate thereof, and pharmaceutical compositions, atopic dermatitis treating agents, and anti-pruritus agents, especially anti-pruritus agents for oral used and for external application, which each contains the said compound as an active ingredient.

  本发明提供了具有激动大麻素受体的活性的化合物，该受体由公式（I）表示：其中R1、R2、R3、R4和G如本文所定义，其药学上可接受的盐或溶剂，以及制备该化合物为活性成分的药物组合物、治疗特应性皮炎的药剂和抗瘙痒剂，尤其是用于口服和外用的抗瘙痒剂。
• NTETRAHYDROPYRIDOTHIOPHENE DERIVATIVES FOR THE TREATMENT OF CANCER
  申请人：4SC AG

  公开号：EP2051983A1

  公开（公告）日：2009-04-29
• [EN] NTETRAHYDROPYRIDOTHIOPHENE DERIVATIVES FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DU N-TÉTRAHYDROPYRIDOTHIOPHÈNE POUR LE TRAITEMENT DU CANCER
  申请人：NYCOMED GMBH

  公开号：WO2008020024A1

  公开（公告）日：2008-02-21

  [EN] Compounds of a certain formula (I), in which Ra and Rb have the meanings indicated in the description, are novel effective compounds with anti-proliferative and apoptosis inducing activity.
  [FR] La présente invention concerne des composés de formule (I) dans laquelle Ra et Rb ont le sens indiqué dans le mémoire descriptif, lesdits composés étant des composés innovants efficaces ayant une activité anti-proliférative et inductrice de l'apoptose.