methyl 3-phenyl-3-(phenylamino)propanoate

• 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 3-phenyl-3-(phenylamino)propanoate
• 英文别名: Methyl 3-(N-phenylamino)-3-phenylpropionate；methyl 3-anilino-3-phenylpropanoate
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: RPZKFVJBHMVQHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  甲基戊酰氯 、 methyl 3-phenyl-3-(phenylamino)propanoate 在 吡啶 、 1,2-二氯乙烷 作用下， 生成 3-(N-methoxyoxalyl-anilino)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  2,3-PYRROLIDINEDIONES. IV. FURTHER STUDIES ON TAUTOMERISM

  摘要：

  DOI：

  10.1021/jo01120a001
• 作为产物：
  描述：

  3,3-dichloro-1,4-diphenylazetidin-2-one 在 锌 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 methyl 3-phenyl-3-(phenylamino)propanoate
  参考文献：
  名称：

  Deslongchamps, Pierre; Caron, Maurice, Canadian Journal of Chemistry, 1980, vol. 58, # 19, p. 2061 - 2068

  摘要：

  DOI：

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。
• One-Pot Silyl Ketene Acetal-Formation Mukaiyama-Mannich Additions to Imines Mediated by Trimethylsilyl Trifluoro­methanesulfonate
  作者：C. Wade Downey、Jared A. Ingersoll、Hadleigh M. Glist、Carolyn M. Dombrowski、Adam T. Barnett

  DOI：10.1002/ejoc.201500958

  日期：2015.11

  the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base, thioesters are readily converted into silyl ketene acetals in situ and undergo Mukaiyama–Mannich addition to N-phenylimines in one pot. The silyl triflate appears to play two roles, activating both the thioester and the imine. This process also works well when thioesters are replaced with amides, esters, or ketones. Products

  在三氟甲磺酸三甲基甲硅烷基酯和三烷基胺碱的存在下，硫酯很容易原位转化为甲硅烷基乙烯酮缩醛，并在一锅中对 N-苯基亚胺进行 Mukaiyama-Mannich 加成。甲硅烷基三氟甲磺酸酯似乎起到两个作用，激活硫酯和亚胺。当硫酯被酰胺、酯或酮取代时，该过程也能很好地工作。产品以脱甲硅烷基苯胺形式分离，无需脱保护步骤。收率范围为 65% 至 99%。
• A simple one-pot three-component reaction for preparation of secondary amines and amino esters mediated by lithium perchlorate
  作者：Mohammad R Saidi、Najmoddin Azizi、Hasan Zali-Boinee

  DOI：10.1016/s0040-4020(01)00636-6

  日期：2001.7

  of several secondary amines and secondary amino esters are reported. Treatment of aldehydes (aliphatic or aromatic) with (trimethylsilyl)alkylamines, in the presence of 5 M lithium perchlorate in diethyl ether gives intermediate imines. Reaction of these intermediate imines with different nucleophiles and functionalized organozinc reagents, BrZnCH2COOR, produce a variety of secondary amines and N-alkyl-

  报道了几种仲胺和仲氨基酯的一锅法合成。在5 M高氯酸锂的乙醚溶液中，用（三甲基甲硅烷基）烷基胺处理醛（脂肪族或芳香族），得到中间体亚胺。这些中间体亚胺与不同的亲核试剂和功能化的有机锌试剂BrZnCH 2 COOR的反应以高收率产生了各种仲胺和N-烷基或N-芳基氨基酯。
• Synthesis of a series of novel chiral Lewis base catalysts and their application in promoting asymmetric hydrosilylation of β-enamino esters
  作者：Xing Chen、Xiao-Yan Hu、Chang Shu、Yong-Hong Zhang、Yong-Sheng Zheng、Yan Jiang、Wei-Cheng Yuan、Bo Liu、Xiao-Mei Zhang

  DOI：10.1039/c3ob40430g

  日期：——

  novel chiral Lewis base catalysts were synthesized from L-serine and applied in the hydrosilylation of β-enamino esters, in which the optimal one promoted the reactions to afford a wide variety of β-amino esters in good yields with good enantioselectivities. It is noteworthy that several cyclic substrates were hydrosilylated under the optimal conditions to give the cyclic β-amino esters with high yields

  合成了一系列新颖的手性路易斯碱催化剂 大号丝氨酸并被用于β-烯氨基酯的氢化硅烷化中，其中最佳的一种促进了反应，以良好的产率和良好的对映选择性提供了多种β-氨基酯。值得注意的是，几种环状底物在最佳条件下被氢化硅烷化，从而得到具有高收率，良好的非对映选择性以及良好的ee值的环状β-氨基酯。
• PREPARATION OF ORGANOZINC HALIDES FROM REACTIVE HALOGEN COMPOUNDS AND THEIR USE
  申请人：CONSORTIUM FUR ELEKTROCHEMISCHE INDUSTRIE GMBH

  公开号：US20030114697A1

  公开（公告）日：2003-06-19

  A process for preparing organozinc halides in solvents, includes reacting a reactive halogen compound with zinc in one or more carboxylic esters. It is also possible to prepare keto, hydroxyl and amino compounds of organozinc halides obtained in a first step from a reactive halogen compound and zinc in one or more carboxylic esters, wherein the organozinc halide obtained is reacted in a second step with an electrophilic reaction partner and the reaction product of the second step is hydrolyzed in a third step.

  在溶剂中制备有机锌卤化物的方法包括将一种或多种羧酸酯中的反应性卤素化合物与锌反应。还可以通过在一种或多种羧酸酯中的反应性卤素化合物和锌的第一步中获得的有机锌卤化物制备酮、羟基和氨基化合物，其中在第二步中将获得的有机锌卤化物与亲电反应伙伴反应，第二步的反应产物在第三步中水解。