6-methyl-4-(benzylamino)-2-pyrone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methyl-4-(benzylamino)-2-pyrone
• 英文别名: 4-benzylamino-6,6-dimethyl-5,6-dihydro-pyran-2-one；4-(benzylamino)-2,2-dimethyl-3H-pyran-6-one
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: SSICIHLWEUCGKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-4-(benzylamino)-2-pyrone 、 3-甲基-2-丁烯醛 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 25.08h， 以88%的产率得到1-Benzyl-2,2,7-trimethylpyrano[4,3-b]pyridin-5-one
  参考文献：
  名称：

  Formal Cycloaddition Reactions of Vinylogous Amides with α,β-Unsaturated Iminiums. A Strategy for Constructing Piperidinyl Heterocycles

  摘要：

  A formal [3 + 3] cycloaddition strategy for constructing piperidinyl heterocycles from vinylogous amides and alpha,beta-unsaturated iminiums is described here, These reactions proceed well, leading to various heterocycles that could serve as useful synthetic building blocks. Comparative studies between the reactivities of vinylogous amides and other 1,3-diketo systems have also been examined. Preferences for the nitrogen atom during the electrocyclic ring closure step are noted in these reactions, and preliminary calculations suggest that these preferences could result from electronic factors.

  DOI：

  10.1021/ol990107v
• 作为产物：
  描述：

  6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione 、 苄胺 以 苯 为溶剂， 生成 6-methyl-4-(benzylamino)-2-pyrone
  参考文献：
  名称：

  金鸡纳生物碱/ TiIV催化的对映选择性烯胺-三氟丙酮酸缩合-环化反应及其在类药物杂环中的应用

  摘要：

  药物设计：金鸡纳生物碱/ Ti IV催化的对映选择性串联烯胺-三氟丙酮酸缩合-环化反应为构建具有季三氟甲基化碳中心的小杂环分子提供了一种可靠的方法（参见方案）。该系列产品是有吸引力的模板，可通过常规方法轻松转化为药物样的三氟甲基化杂环。

  DOI：

  10.1002/chem.201000911

文献信息

• Formal Cycloaddition Reactions of Vinylogous Amides with α,β-Unsaturated Iminiums. A Strategy for Constructing Piperidinyl Heterocycles
  作者：Richard P. Hsung、Lin-Li Wei、Heather M. Sklenicka、Christopher J. Douglas、Michael J. McLaughlin、Jason A. Mulder、Letitia J. Yao

  DOI：10.1021/ol990107v

  日期：1999.8.1

  A formal [3 + 3] cycloaddition strategy for constructing piperidinyl heterocycles from vinylogous amides and alpha,beta-unsaturated iminiums is described here, These reactions proceed well, leading to various heterocycles that could serve as useful synthetic building blocks. Comparative studies between the reactivities of vinylogous amides and other 1,3-diketo systems have also been examined. Preferences for the nitrogen atom during the electrocyclic ring closure step are noted in these reactions, and preliminary calculations suggest that these preferences could result from electronic factors.
• Cinchona Alkaloid/Ti^IV-Catalyzed Enantioselective Enamine-Trifluoropyruvate Condensation-Cyclization Reaction and Its Application to Drug-like Heterocycles
  作者：Shinichi Ogawa、Norihito Iida、Etsuko Tokunaga、Motoo Shiro、Norio Shibata

  DOI：10.1002/chem.201000911

  日期：2010.6.25

  design: A cinchona alkaloid/TiIV‐catalyzed enantioselective tandem enamine–trifluoropyruvate condensation–cyclization reaction provides a robust method for the construction of small heterocyclic molecules with a quaternary trifluoromethylated carbon center (see scheme). The series of products are attractive templates and were readily converted to drug‐like trifluoromethylated heterocycles by conventional

  药物设计：金鸡纳生物碱/ Ti IV催化的对映选择性串联烯胺-三氟丙酮酸缩合-环化反应为构建具有季三氟甲基化碳中心的小杂环分子提供了一种可靠的方法（参见方案）。该系列产品是有吸引力的模板，可通过常规方法轻松转化为药物样的三氟甲基化杂环。