3-(4-chlorophenyl)-2,2-dimethyl-3-phenylaminopropionic acid methyl ester

• 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: 3-(4-chlorophenyl)-2,2-dimethyl-3-phenylaminopropionic acid methyl ester
• 英文别名: 2,2-dimethyl-3-(4-chlorophenyl)-3-phenylaminopropinoic acid methyl ester；methyl 2,2-dimethyl-3-(N-phenylamino)-3-(4-chlorophenyl)propanoate；methyl 3-(4-chlorophenyl)-2,2-dimethyl-3-(phenylamino)propanoate；methyl 2,2-dimethyl-3-(4-chlorophenyl)-3-(N-phenylamino)propanoate；Methyl 3-anilino-3-(4-chlorophenyl)-2,2-dimethylpropanoate
• 化学式: C₁₈H₂₀ClNO₂
• 分子量: 317.815
• InChiKey: NBAQSONVXSEHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 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

• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 (E)-1-(4-chlorophenyl)-N-phenylmethanimine 在 lithium perfluorooctane sulfonate 作用下， 以 various solvent(s) 为溶剂， 50.0 ℃ 、9.0 MPa 条件下， 反应 10.0h， 以60%的产率得到3-(4-chlorophenyl)-2,2-dimethyl-3-phenylaminopropionic acid methyl ester
  参考文献：
  名称：

  Lithium heptadecafluorooctanesulfonate catalyzed Mannich-type and aza-Diels–Alder reactions in supercritical carbon dioxide

  摘要：

  The Mannich-type reaction of imines with (1-methoxy-2-methylpropenyloxy)trimethylsilane and aza-Diels-Alder reaction of imines with Danishefsky's diene can be carried out in scCO(2) in the presence of lithium heptadecafluorooctanesulfonate which offer a way to synthesize beta-amino carbonyl compounds and nitrogen-containing six-membered ring compounds under environmentally benign conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.065

文献信息

• 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。
• Cationic iridium complex is a new and efficient Lewis acid catalyst for aldol and Mannich reactions
  作者：Gen Onodera、Takayuki Toeda、Nou-no Toda、Daigo Shibagishi、Ryo Takeuchi

  DOI：10.1016/j.tet.2010.09.015

  日期：2010.11

  A cationic iridium complex [Ir(cod)2]SbF6 was found to be a new and efficient Lewis acid catalyst for Mukaiyama aldol and Mannich reactions. Aldehydes react smoothly with silyl enol ethers to give β-siloxy ketones in the presence of 0.5 mol % of [Ir(cod)2]SbF6. The reaction of N-alkyl arylaldimines with ketene silyl acetals in the presence of 5 mol % [Ir(cod)2]SbF6/P(OPh)3 gave β-amino esters. After

  发现阳离子铱络合物[Ir（cod）2 ] SbF 6是用于Mukaiyama aldol和Mannich反应的新型高效路易斯酸催化剂。醛在0.5摩尔％[Ir（cod）2 ] SbF 6的存在下与甲硅烷基烯醇醚平稳反应，生成β-甲硅烷氧基酮。在5mol％[Ir（cod）2 ] SbF 6 / P（OPh）3的存在下，N-烷基芳基醛亚胺与乙烯酮甲硅烷基缩醛的反应得到β-氨基酯。在曼尼希反应完成后，将反应混合物搅拌24小时导致环化，得到β-内酰胺。N的反应苯乙二胺与芳基苯甲二胺与由苯乙酮衍生的甲硅烷基烯醇醚得到的四氢喹啉衍生物为单一的非对映异构体。
• TTMPP Catalyzed One-pot Silyl Ketene Acetal–Imine Condensation Route to β-Lactams
  作者：Satoru Matsukawa、Kayoko Obu

  DOI：10.1246/cl.2004.1626

  日期：2004.12

  Highly nucleophilic phosphine, tris(2,4,6-trimethoxy phenyl) phosphine (TTMPP) catalyzes a unique one-pot cyclization reaction between silyl ketene acetal and aldimine, resulting in β-lactam.

  高度亲核性膦，三（2,4,6-三甲氧基苯基）膦（TTMPP）催化甲硅烷基乙烯酮缩醛和醛亚胺之间独特的一锅环化反应，生成β-内酰胺。
• Mannich-type reaction of (1-methoxy-2-methylpropenyloxy)trimethylsilane with arylaldehydes and aromatic amines catalyzed by perfluorinated rare earth metal salts in fluorous phase
  作者：Min Shi、Shi-Cong Cui、Ying-Hao Liu

  DOI：10.1016/j.tet.2005.03.059

  日期：2005.5

  reaction in fluorous phase. By use of perfluorodecalin (C10F18, cis- and trans-mixture) as a fluorous solvent and perfluorinated rare earth metal salts such as Sc(OSO2C8F17)3 or Yb(OSO2C8F17)3 (2.0 mol%) as a catalyst, the Mannich-type reaction of arylaldehydes with aromatic amines and (1-methoxy-2-methylpropenyloxy)trimethylsilane can be performed for many times without reloading the catalyst and the

  在本文中，我们描述了在荧光相中有用的曼尼希型反应。通过使用全氟萘烷（C 10 F 18，顺式和反式混合物）作为氟溶剂和全氟化稀土金属盐，例如Sc（OSO 2 C 8 F 17）3或Yb（OSO 2 C 8 F 17）3通过使用（2.0摩尔％）作为催化剂，芳醛与芳族胺和（1-甲氧基-2-甲基丙烯氧基）三甲基硅烷的曼尼希型反应可以进行多次，而无需重新装载催化剂和氟溶剂。
• Mannich‐Type Reaction Catalyzed by Silica‐Supported Fluoroboric Acid under Solvent‐Free Conditions
  作者：WeiYi Chen、XinSheng Li、Jun Lu

  DOI：10.1080/00397910701796766

  日期：2008.1.1

  Abstract Three‐component Mannich‐type reaction of aldehydes, aromatic amines, and silyl enolate proceeded smoothly to afford β‐amino carbonyl compounds with good yields in the presence of a catalytic amount of HBF4‐SiO2.

  摘要 在催化量的 HBF4-SiO2 存在下，醛、芳香胺和甲硅烷基烯醇酯的三组分曼尼希型反应顺利进行，以良好的收率得到 β-氨基羰基化合物。