methyl 2,2-dimethyl-3-phenyl-3-(phenylamino)propanoate | 23958-65-8

• 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: methyl 2,2-dimethyl-3-phenyl-3-(phenylamino)propanoate
• 英文别名: methyl 2,2-dimethyl-3-phenyl-3-(N-phenylamino)propionate；2,2-dimethyl-3-phenyl-3-phenylaminopropionic acid methyl ester；Methyl 3-anilino-2,2-dimethyl-3-phenylpropanoate
• CAS: 23958-65-8
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: UGZTXYZHZQUOIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  methyl 2,2-dimethyl-3-phenyl-3-(phenylamino)propanoate 在 4-二甲氨基吡啶 、 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 N-(2,2-dimethyl-1-phenylpent-3-yn-1-yl)-N-phenylpentanamide
  参考文献：
  名称：

  Stereodefined Homopropargyl Amines by Tandem Nucleophilic Addition/Fragmentation of Dihydropyridone Triflates

  摘要：

  Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available beta-amino esters.

  DOI：

  10.1021/ol102760q
• 作为产物：
  描述：

  苯胺 在 magnesium sulfate 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 methyl 2,2-dimethyl-3-phenyl-3-(phenylamino)propanoate
  参考文献：
  名称：

  Stereodefined Homopropargyl Amines by Tandem Nucleophilic Addition/Fragmentation of Dihydropyridone Triflates

  摘要：

  Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available beta-amino esters.

  DOI：

  10.1021/ol102760q

文献信息

• Lewis acid catalysis in a supercritical carbon dioxide (scCO2)-poly(ethylene glycol) derivatives (PEGs) system: remarkable effect of PEGS as additives on reactivity of Ln(OTf)3-catalyzed Mannich and aldol reactions in scCO2
  作者：Ichiro Komoto、Shū Kobayashi

  DOI：10.1039/b106437c

  日期：——

  Use of poly(ethylene glycol) derivatives (PEGs) as additives in supercritical carbon dioxide (scCO2) was found to be effective for Mannich and aldol reactions of silyl enolates with aldehydes and imines, and formation of emulsions was observed in these systems.

  聚乙二醇（PEG）衍生物作为添加剂在超临界二氧化碳（scCO2）中的应用，已被发现对于硅基烯醇盐与醛和亚胺的Mannich反应和aldol反应是有效的，并且在这些系统中观察到了乳液的形成。
• Strong Lewis acid air-stable cationic titanocene perfluoroalkyl(aryl)sulfonate complexes as highly efficient and recyclable catalysts for C–C bond forming reactions
  作者：Ningbo Li、Jinying Wang、Xiaohong Zhang、Renhua Qiu、Xie Wang、Jinyang Chen、Shuang-Feng Yin、Xinhua Xu

  DOI：10.1039/c4dt00549j

  日期：——

  A series of titanocene perfluoroalkyl(aryl)sulfonate complexes were synthesized, characterized, and applied in various C–C bond forming reactions.

  一系列的钛ocene基过氟烷基（芳基）磺酸盐配合物被合成、表征，并应用于各种C-C键形成反应。
• Imino-Diels–Alder and imino-aldol reactions catalyzed by samarium diiodide
  作者：Jacqueline Collin、Nada Jaber、Marie Isabelle Lannou

  DOI：10.1016/s0040-4039(01)01581-7

  日期：2001.10

  In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones.

  在二氯甲烷中催化量的二碘化sa存在下，芳族亚胺与Danishefsky二烯反应形成高产率的四氢吡啶-4-酮。在相同条件下，各种亚氨基-羟醛反应可得到β-氨基酯或β-氨基酮。
• Brønsted Acid-Catalyzed Mannich-Type Reactions in Aqueous Media
  作者：Takahiko Akiyama、Jun Takaya、Hirotaka Kagoshima

  DOI：10.1002/1615-4169(200206)344:3/4<338::aid-adsc338>3.0.co;2-o

  日期：2002.6

  aldimines took place smoothly in aqueous organic solvent to afford β-aminocarbonyl compounds in high yields. The HBF4-catalyzed Mannich-type reaction also proceeded smoothly in water without organic solvent in the presence of a surfactant. A three-component synthesis starting from aldehyde, amine, and silyl enolate was successfully realized by means of a Bronsted acid in aqueous media.

  HBF4催化的甲硅烷基烯醇化物与醛亚胺的曼尼希型反应在水性有机溶剂中顺利进行，以高产率得到β-氨基羰基化合物。在表面活性剂存在下，HBF4催化的曼尼希型反应在没有有机溶剂的水中也能顺利进行。借助布朗斯台德酸在水性介质中成功实现了从醛、胺和烯醇甲硅烷基开始的三组分合成。
• Synthesis of β-Amino Esters by Bismuth Triflate Catalyzed Three-Component Mannich-Type Reaction
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1055/s-2005-923594

  日期：——

  Bismuth triflate catalyzes the Mannich-type reaction of a variety of in situ generated aldimines using aldehydes, anilines, and silyl enol ethers in a three-component reaction. The reaction proceeds rapidly and affords the corresponding protected beta-amino ketones in high yields (up to 94%).

  三氟甲磺酸铋使用醛、苯胺和甲硅烷基烯醇醚在三组分反应中催化各种原位生成的醛亚胺的曼尼希型反应。反应进行得很快，并以高产率（高达 94%）提供相应的受保护的 β-氨基酮。