5-(tert-butyl)-N,N-dimethylfuran-2-carboxamide | 158687-81-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(tert-butyl)-N,N-dimethylfuran-2-carboxamide
• 英文别名: 5-tert-butyl-N,N-dimethylfuran-2-carboxamide
• CAS: 158687-81-1
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: RNGVHUKXWALUMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(tert-butyl)-N,N-dimethylfuran-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以83%的产率得到5-t-butyl-2-N,N-dimethylfurfurylamine
  参考文献：
  名称：

  Cholinergic agents structurally related to furtrethonium. 1

  摘要：

  A series of 5-substituted-2-(dimethylaminomethyl)-furyl derivatives 4 was prepared, with the aim of discovering novel antimuscarinic agents which are selective for smooth muscle as opposed to cardiac tissue. Both non-quaternary and quaternary ammonium compounds were synthesised. The agonist starting point, furtrethonium 3, was gradually transformed into antagonist by introduction of lipophilic and bulky groups in position 5 of this molecule. In particular, the introduction of alpha-hydroxy-alpha-cyclohexylbenzyl moiety (compound 9b), a lipophilic group characteristic of antimuscarinic agents, caused an appreciable increase of the antagonist's potency, and the lengthening of the distance between this lipophilic group and the furan ring, obtained by introduction of an ester, ether or amide group, led to some selectivity towards smooth muscle (compounds 19, 21, 25). Interestingly, compound 19, with an ester moiety as a spacer group, proved to be at least 20 times more potent in rat ileum (pK(B) = 7.3) and rat bladder (pK(B) = 7.2) than guinea-pig atria (pK(B) = 5.9).

  DOI：

  10.1016/0223-5234(94)90213-5
• 作为产物：
  描述：

  5-叔丁基呋喃-2-羧酸 在 氯化亚砜 作用下， 反应 3.0h， 生成 5-(tert-butyl)-N,N-dimethylfuran-2-carboxamide
  参考文献：
  名称：

  Cholinergic agents structurally related to furtrethonium. 1

  摘要：

  A series of 5-substituted-2-(dimethylaminomethyl)-furyl derivatives 4 was prepared, with the aim of discovering novel antimuscarinic agents which are selective for smooth muscle as opposed to cardiac tissue. Both non-quaternary and quaternary ammonium compounds were synthesised. The agonist starting point, furtrethonium 3, was gradually transformed into antagonist by introduction of lipophilic and bulky groups in position 5 of this molecule. In particular, the introduction of alpha-hydroxy-alpha-cyclohexylbenzyl moiety (compound 9b), a lipophilic group characteristic of antimuscarinic agents, caused an appreciable increase of the antagonist's potency, and the lengthening of the distance between this lipophilic group and the furan ring, obtained by introduction of an ester, ether or amide group, led to some selectivity towards smooth muscle (compounds 19, 21, 25). Interestingly, compound 19, with an ester moiety as a spacer group, proved to be at least 20 times more potent in rat ileum (pK(B) = 7.3) and rat bladder (pK(B) = 7.2) than guinea-pig atria (pK(B) = 5.9).

  DOI：

  10.1016/0223-5234(94)90213-5

文献信息

• Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents
  作者：Wenkun Luo、Yongjie Yang、Bo Liu、Biaolin Yin

  DOI：10.1021/acs.joc.0c01002

  日期：2020.7.17

  protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fashion. Mechanistic studies suggest that the reaction proceeds via generation of an alkyl radical from the alkyl aldehyde, addition of the radical to

  已经开发出使用烷基醛作为烷基化剂的FeCl 2催化酰基呋喃的氧化脱羰基α-烷基化的方案。该方案以实用和可持续的方式提供中等至良好收率的α-烷基-α-酰基呋喃。机理研究表明，该反应是通过由烷基醛生成烷基，将自由基加至呋喃环并随后进行重新芳构化来进行的。
• Substituted Quinazoline and Pyrido-Pyrimidine Derivatives
  申请人：Smith Roger Astbury

  公开号：US20120129851A1

  公开（公告）日：2012-05-24

  The present application provides novel substituted quinazoline and pyrido-pyrimidine compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating PI3K and/or mTOR activity by administering a therapeutically effective amount of one or more of the compounds to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the PI3K/AKT/mTOR pathway. Advantageously, these compounds perform as dual PI3K/mTOR inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.

  本申请提供了新型的取代喹唑啉和吡啶并嘧啶化合物及其药学上可接受的盐。同时还提供了制备这些化合物的方法。通过向患者投予一种或多种化合物的治疗有效剂量，这些化合物有助于共同调节PI3K和/或mTOR活性。通过这样做，这些化合物有效地治疗与PI3K/AKT/mTOR通路失调相关的疾病。优点是，这些化合物具有双重PI3K/mTOR抑制剂的作用。这些化合物可以治疗多种疾病，包括以炎症或异常细胞增殖为特征的疾病。在一种实施方式中，该疾病是癌症。
• SUBSTITUTED QUINAZOLINE AND PYRIDO-PYRIMIDINE DERIVATIVES
  申请人：Asana Biosciences, LLC

  公开号：US20150011547A1

  公开（公告）日：2015-01-08

  The present application provides novel substituted quinazoline and pyrido-pyrimidine compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating PI3K and/or mTOR activity by administering a therapeutically effective amount of one or more of the compounds to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the PI3K/AKT/mTOR pathway. Advantageously, these compounds perform as dual PI3K/mTOR inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.

  本申请提供了新颖的取代喹唑啉和吡啶并嘧啶化合物及其药学上可接受的盐。还提供了制备这些化合物的方法。通过向患者投予一种或多种化合物的治疗有效量，这些化合物可用于共调节PI3K和/或mTOR活性。通过这样做，这些化合物有效地治疗与PI3K / AKT / mTOR通路失调相关的疾病。有利的是，这些化合物作为双重PI3K / mTOR抑制剂发挥作用。这些化合物可用于治疗各种疾病，包括以炎症或异常细胞增殖为特征的疾病。在一种实施方式中，该疾病是癌症。
• US8440662B2
  申请人：——

  公开号：US8440662B2

  公开（公告）日：2013-05-14
• US9115092B2
  申请人：——

  公开号：US9115092B2

  公开（公告）日：2015-08-25