5-叔丁基-4-羟基甲基-2-甲基-呋喃-3-羧酸 | 462068-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-叔丁基-4-羟基甲基-2-甲基-呋喃-3-羧酸
• 英文名称: 2-methyl-4-hydroxymethyl-5-tert-butylfuran-3-carboxylic acid
• 英文别名: 5-tert-butyl-4-hydroxymethyl-2-methyl-furan-3-carboxylic acid；5-tert-butyl-4-(hydroxymethyl)-2-methylfuran-3-carboxylic acid
• CAS: 462068-43-5
• 化学式: C₁₁H₁₆O₄
• mdl: MFCD02737949
• 分子量: 212.246
• InChiKey: FDSKGVGFTCCVAG-UHFFFAOYSA-N

物化性质

• 沸点：
  257.8±20.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  5-叔丁基-4-羟基甲基-2-甲基-呋喃-3-羧酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 7.0h， 以2.2 g的产率得到2-methyl-4-chloromethyl-5-tert-butylfuran-3-carboxylic acid chloride
  参考文献：
  名称：

  摘要：

  3-Ethoxycarbonyl- and 3-acetyl-2-methyl-5-tert-butylfurans undergo chloromethylation under the unusually rigorous conditions (55-60degreesC, 3-3.5 h). The corresponding diethylamide and nitrite were prepared by standard modification of the carboxy group. In phosphorylation of the resulting chloromethylfurans under the conditions of the Michaelis-Becker reaction, in the case of the ester and diethylamide, the phosphonate yields were close to those obtained with compounds containing no tert-butoxy group, and in the case of acetylfuran the yield was even somewhat higher. On the contrary, the chloromethylated nitrite reacts considerably more slowly than all the other compounds under consideration and than the similar compound containing no tert-butyl substituent. Thus,,the effect of the tert-butyl group in the a-position of the furan ring is clearly pronounced in the electrophilic substitutions in the neighboring position of the heteroring. When the reaction center is located in the side chain (substitution of chlorine), the effect of the bulky substituent is manifested only in special cases and can be attributed to the presence of a conformation in which the chloromethyl group is shielded.

  DOI：

  10.1023/a:1020750715942
• 作为产物：
  描述：

  2-methyl-5-(tert-butyl)furan-3-carboxylic acid ethyl ester 在 盐酸 、 氢氧化钾 、 zinc(II) chloride 作用下， 以 乙醇 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 5-叔丁基-4-羟基甲基-2-甲基-呋喃-3-羧酸
  参考文献：
  名称：

  摘要：

  3-Ethoxycarbonyl- and 3-acetyl-2-methyl-5-tert-butylfurans undergo chloromethylation under the unusually rigorous conditions (55-60degreesC, 3-3.5 h). The corresponding diethylamide and nitrite were prepared by standard modification of the carboxy group. In phosphorylation of the resulting chloromethylfurans under the conditions of the Michaelis-Becker reaction, in the case of the ester and diethylamide, the phosphonate yields were close to those obtained with compounds containing no tert-butoxy group, and in the case of acetylfuran the yield was even somewhat higher. On the contrary, the chloromethylated nitrite reacts considerably more slowly than all the other compounds under consideration and than the similar compound containing no tert-butyl substituent. Thus,,the effect of the tert-butyl group in the a-position of the furan ring is clearly pronounced in the electrophilic substitutions in the neighboring position of the heteroring. When the reaction center is located in the side chain (substitution of chlorine), the effect of the bulky substituent is manifested only in special cases and can be attributed to the presence of a conformation in which the chloromethyl group is shielded.

  DOI：

  10.1023/a:1020750715942

文献信息

• SUBSTITUTED BENZIMDAZOLE DERIVATIVES USEFUL AS TRPM8 RECEPTOR MODULATORS
  申请人：PLAYER Mark R.

  公开号：US20120202856A1

  公开（公告）日：2012-08-09

  The present invention is directed to benzimidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by TRP M8, including for example, inflammatory pain, inflammatory hyperalgesia, inflammatory hypersensitivity condition, neuropathic pain, neuropathic cold allodynia, inflammatory somatic hyperalgesia, inflammatory visceral hyperalgesia, cardiovascular disease aggravated by cold and pulmonary disease aggravated by cold.

  本发明涉及苯并咪唑衍生物，包含它们的药物组合物以及它们在治疗由TRP M8调节的疾病和症状中的应用，例如炎症性疼痛、炎症性过敏症、炎症性过敏性疾病、神经病性疼痛、神经性寒冷触痛、炎症性体部过敏症、炎症性内脏过敏症、受冷加重的心血管疾病和受冷加重的肺部疾病。
• ——
  作者：L. M. Pevzner

  DOI：10.1023/a:1020750715942

  日期：——

  3-Ethoxycarbonyl- and 3-acetyl-2-methyl-5-tert-butylfurans undergo chloromethylation under the unusually rigorous conditions (55-60degreesC, 3-3.5 h). The corresponding diethylamide and nitrite were prepared by standard modification of the carboxy group. In phosphorylation of the resulting chloromethylfurans under the conditions of the Michaelis-Becker reaction, in the case of the ester and diethylamide, the phosphonate yields were close to those obtained with compounds containing no tert-butoxy group, and in the case of acetylfuran the yield was even somewhat higher. On the contrary, the chloromethylated nitrite reacts considerably more slowly than all the other compounds under consideration and than the similar compound containing no tert-butyl substituent. Thus,,the effect of the tert-butyl group in the a-position of the furan ring is clearly pronounced in the electrophilic substitutions in the neighboring position of the heteroring. When the reaction center is located in the side chain (substitution of chlorine), the effect of the bulky substituent is manifested only in special cases and can be attributed to the presence of a conformation in which the chloromethyl group is shielded.