methyl 2,2-dimethyl-3-(phenylamino)-3-(2-pyridyl)propanoate | 79388-25-3

• 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-(phenylamino)-3-(2-pyridyl)propanoate
• 英文别名: Methyl 3-anilino-2,2-dimethyl-3-pyridin-2-ylpropanoate
• CAS: 79388-25-3
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: ICTORNBWXFAEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dimethyl-3-(phenylamino)-3-(2-pyridyl)propanoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以91%的产率得到3,3-dimethyl-1-phenyl-4-pyridin-2-ylazetidin-2-one
  参考文献：
  名称：

  Convenient Synthesis of β-Lactams by the Reaction of Ketene Silyl Acetals with Schiff Bases Promoted by Titanium(IV) Chloride

  摘要：

  DOI：

  10.1055/s-1981-29520
• 作为产物：
  描述：

  2-(phenyliminomethyl)pyridine 、 1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 在 titanium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以81%的产率得到methyl 2,2-dimethyl-3-(phenylamino)-3-(2-pyridyl)propanoate
  参考文献：
  名称：

  Convenient Synthesis of β-Lactams by the Reaction of Ketene Silyl Acetals with Schiff Bases Promoted by Titanium(IV) Chloride

  摘要：

  DOI：

  10.1055/s-1981-29520

文献信息

• Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of [Rh(COD)Cl]₂and TMS-CN under Almost Neutral Conditions
  作者：Tsunehiko Soga、Haruhiro Takenoshita、Masaaki Yamada、Teruaki Mukaiyama

  DOI：10.1246/bcsj.63.3122

  日期：1990.11

  In the presence of a catalytic amount of a transition metal compound such as [Rh(COD)Cl]2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields. In the coexistence of catalytic amounts of [Rh(COD)Cl]2 and TMS-CN, silyl enol ethers or ketene silyl acetals react with acetals, aldehyes, or imines to yield the corresponding coupling products in good yields under almost neutral conditions.

  在[Rh(COD)Cl]2、Co(acac)2或NiCl2等过渡金属化合物的催化量存在下，三甲基硅基氰与缩醛顺利反应，以良好的产率生成α-甲氧基腈。在[Rh(COD)Cl]2和TMS-CN的催化量共存下，硅基烯醇醚或烯酮硅基缩醛与缩醛、醛或亚胺反应，在近乎中性的条件下以良好的产率生成相应的偶联产物。
• Water-Accelerated Aldol Reaction of Ketene Silyl Acetals with Carbonyl Compounds
  作者：Teck-Peng Loh、Li-Chun Feng、Lin-Li Wei

  DOI：10.1016/s0040-4020(00)00630-x

  日期：2000.9

  The aldol reactions of ketene silyl acetals with reactive aldehydes proceed smoothly in water to afford the corresponding aldol products in good yields.

  乙烯酮甲硅烷基缩醛与反应性醛的醛醇缩合反应在水中可顺利进行，从而以高收率得到相应的醛醇缩合产物。
• Design and Synthesis of a Water-Tolerant Chiral Indium Complex: ­Application to One-Pot Three-Component Mannich-Type Reactions in Water
  作者：Teck-Peng Loh、Jian Xiao

  DOI：10.1055/s-2007-970774

  日期：2007.3

  A novel chiral indium(III) camphorsulfonate complex prepared from indium trichloride, allyltributylstannane and (1S)-(+)-10-camphorsulfonic acid has been developed as a water-tolerant Lewis acid to afford high yields (up to 99%) in one-pot three-component Mannich-type reactions in a true water environment.

  由三氯化铟、烯丙基三丁基锡烷和(1S)-(+)-10-樟脑磺酸制备的新型手性樟脑磺酸铟(III)络合物已被开发成一种耐水路易斯酸，可在真水环境中通过单锅三组分曼尼希式反应获得高产率（高达 99%）。
• Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters
  作者：Teck-Peng Loh、Lin-Li Wei

  DOI：10.1016/s0040-4039(97)10478-6

  日期：1998.1

  Novel one-pot Mannich-type reaction between aldehydes, amines and silyl enol ethers is catalyzed by indium trichloride in water to give β-amino ketones and esters in moderate to good yields.

  水中的三氯化铟催化醛，胺和甲硅烷基烯醇醚之间的新型一锅法曼尼希式反应，以中等至良好的收率得到β-氨基酮和酯。
• Three Component Synthesis of β-Amino Carbonyl Compounds Using Indium Trichloride-Catalyzed One-pot Mannich-type Reaction in Water
  作者：Teck-Peng Loh、Sarah B.K.W. Liung、Kee-Leng Tan、Lin-Li Wei

  DOI：10.1016/s0040-4020(00)00221-0

  日期：2000.5

  The use of indium trichloride as catalyst in a one-pot Mannich reaction in water gives high yields for the formation of beta-aminoketones/esters/acids is described. The catalyst can be recycled when the reaction is complete (Loh T.-P.; Wei L.-L. Tetrahedron Lett. 1998, 39, 323). (C) 2000 Elsevier Science Ltd. All rights reserved.