methyl-3-(N,N-dibenzylamino)-3-phenylpropanoate | 160947-61-5

• 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: methyl-3-(N,N-dibenzylamino)-3-phenylpropanoate
• 英文别名: Methyl 3-(dibenzylamino)-3-phenylpropanoate
• CAS: 160947-61-5
• 化学式: C₂₄H₂₅NO₂
• 分子量: 359.468
• InChiKey: FFAAPXNPOIQBGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene 、 methyl-3-(N,N-dibenzylamino)-3-phenylpropanoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(3R,4S)-3-[(R)-(dibenzylamino)-phenylmethyl]-1-(4-methoxyphenyl)-4-[(4-methoxyphenyl)iminomethyl]azetidin-2-one
  参考文献：
  名称：

  Preparation of .alpha.-Methylene and .alpha.-Ethylidene .beta.-Lactams via the Ester Enolate-Imine Condensation Using .beta.-(Dialkylamino) Esters as Starting Materials: Scope and Synthetic Applications

  摘要：

  A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.

  DOI：

  10.1021/jo00105a013
• 作为产物：
  描述：

  lithium dibenzylamide 、 肉桂酸甲酯 生成 methyl-3-(N,N-dibenzylamino)-3-phenylpropanoate
  参考文献：
  名称：

  Preparation of .alpha.-Methylene and .alpha.-Ethylidene .beta.-Lactams via the Ester Enolate-Imine Condensation Using .beta.-(Dialkylamino) Esters as Starting Materials: Scope and Synthetic Applications

  摘要：

  A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.

  DOI：

  10.1021/jo00105a013

文献信息

• Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins
  作者：Stephen G. Davies、Ai M. Fletcher、James A. Lee、Paul M. Roberts、Myriam Y. Souleymanou、James E. Thomson、Charlotte M. Zammit

  DOI：10.1039/c4ob00274a

  日期：——

  The diastereoselective Ireland–Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from

  一系列取代的烯丙基β-氨基酯的非对映选择性爱尔兰-克莱森重排产生了具有良好非对映选择性的相应对映体纯α-取代-β-氨基酯。通过重排一系列由山梨酸衍生的β-氨基酯，证明了该方法在不对称合成一系列C（5）-取代的1,2-抗-1,5-顺反戊糖中的应用。然后进行酯化反应，闭环复分解反应，氢解脱保护/还原反应和水解反应，仅需9步即可从市售原料中获得C（5）-取代的反式戊烷。
• B(OMe)₃as a Nonacidic Iminium Ion Generator in Mannich- and Ugi-Type Reactions
  作者：Yusuke Tanaka、Kousuke Hidaka、Tomoaki Hasui、Michinori Suginome

  DOI：10.1002/ejoc.200801190

  日期：2009.3

  Mannich-type reactions of aldehydes with secondary amines and a ketene silyl acetal were promoted by trimethoxyborane in DMSO to afford the corresponding β-amino esters in good yields. B(OMe)3 also promoted Ugi-type reactions ofaldehydes with secondary amines and isocyanides in 1,2-dichloroethane, which leads to the formation of α-amino amides. In these reactions, trimethoxyborane serves as an inexpensive

  三甲氧基硼烷在 DMSO 中促进醛与仲胺和乙烯酮甲硅烷基缩醛的曼尼希型反应，以良好的产率得到相应的 β-氨基酯。B(OMe)3 还促进醛与仲胺和异氰化物在 1,2-二氯乙烷中的 Ugi 型反应，从而形成 α-氨基酰胺。在这些反应中，三甲氧基硼烷用作廉价、市售且几乎非酸性的亚胺离子发生器。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-Type Reaction Using Secondary Amines, Aldehydes, and Ketene Silyl Acetals
  作者：Michinori Suginome、Yusuke Tanaka、Tomoaki Hasui

  DOI：10.1055/s-2008-1072724

  日期：2008.5

  Reactions of secondary amines, aldehydes, and ketene silyl acetals were efficiently promoted by catalytic amounts of diarylborinic acid esters, Ar 2 B(OR), affording β-amino esters selectively with no formation of the corresponding β-hydroxy esters.

  催化量的二芳基硼酸酯 Ar 2 B(OR) 有效地促进了仲胺、醛和乙烯酮甲硅烷基缩醛的反应，选择性地提供了 β-氨基酯，而不会形成相应的 β-羟基酯。