2-methyl-5-bromo-3-hydroxymethylfuran | 35304-36-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-methyl-5-bromo-3-hydroxymethylfuran
• 英文别名: (5-bromo-2-methylfuran-3-yl)methanol
• CAS: 35304-36-0
• 化学式: C₆H₇BrO₂
• 分子量: 191.024
• InChiKey: KAZNOJQIZKFQJU-UHFFFAOYSA-N

物化性质

• 沸点：
  130.2±10.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-5-bromo-3-hydroxymethylfuran 在 manganese dioxide manganese dioxide 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以to give the title compound (2.8 g, 51%) as a white solid的产率得到5-bromo-2-methylfuran-3-carbaldehyde
  参考文献：
  名称：

  HETEROCYCLIC COMPOUND

  摘要：

  本发明提供了一种由以下式（I）表示的杂环化合物，该化合物具有葡萄糖高升素拮抗作用，并可用于预防或治疗糖尿病等疾病，其中，式中环A为可选取代苯环等；Y为氮原子等；X为—O—等；R4为氢原子等；R5和R6各自独立地为氢原子等；R1为可选取代的碳氢基团等；R2为氢原子等；R3为—（CH2）3—COOH等，或其盐。

  公开号：

  US20100256156A1
• 作为产物：
  描述：

  5-溴-2-甲基-3-呋喃羧酸甲酯 在 lithium aluminium tetrahydride 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到2-methyl-5-bromo-3-hydroxymethylfuran
  参考文献：
  名称：

  HETEROCYCLIC COMPOUND AS GLUCAGON ANTAGONIST

  摘要：

  公开号：

  EP2210876B1

文献信息

• Heterocyclic compound
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US08309580B2

  公开（公告）日：2012-11-13

  The present invention provides a heterocyclic compound represented by the following formula (I), which has a glucagon antagonistic action and is useful for the prophylaxis or treatment of diabetes and the like, a compound represented by wherein ring A is an optionally substituted benzene ring and the like; Y is a nitrogen atom and the like; X is —O— and the like; R4 is a hydrogen atom and the like; R5 and R6 are each independently a hydrogen atom and the like; R1 is an optionally substituted hydrocarbon group and the like; R2 is a hydrogen atom and the like; and R3 is —(CH2)3—COOH and the like, or a salt thereof.

  本发明提供了一种杂环化合物，其由以下式子（I）表示，具有葡萄糖升高素拮抗作用，用于预防或治疗糖尿病等疾病，其中化合物由以下表示： 其中环A是可选取代的苯环等；Y是氮原子等；X是—O—等；R4是氢原子等；R5和R6各自独立地是氢原子等；R1是可选取代的烃基等；R2是氢原子等；R3是—（CH2）3—COOH等，或其盐。
• Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans
  作者：L. M. Pevzner

  DOI：10.1134/s1070363209030050

  日期：2009.3

  Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.
• US8309580B2
  申请人：——

  公开号：US8309580B2

  公开（公告）日：2012-11-13