[(3-pyridyl-methylidene)-amino]-acetic acid ethyl ester | 169962-96-3

• 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: [(3-pyridyl-methylidene)-amino]-acetic acid ethyl ester
• 英文别名: ethyl (E)-2-((pyridin-3-ylmethylene)amino)acetate；N-(pyridin-3-ylmethylene)glycine ethyl ester；N-(3-pyridylmethylene)glycine ethyl ester
• CAS: 169962-96-3
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: KZZIJSGBLQQSKK-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.55
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(3-pyridyl-methylidene)-amino]-acetic acid ethyl ester 在 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 ethyl (2S,3S,4S,5R)-3-(1,2-O-isopropylidene-3-O-benzyl-β-L-threo-furanos-4-yl)-5-(3-pyridyl)-proline-4-carboxylate
  参考文献：
  名称：

  Diastereoselective synthesis of glycosylated prolines as α-glucosidase inhibitors and organocatalyst in asymmetric aldol reaction

  摘要：

  1,3-Dipolar cycloaddition of azomethine ylides and glycosyl E-olefins in presence of LDA led to diastereoselective formation of C-glycosylated proline esters. The selected esters on regioselective hydrolysis with LiOH gave C-glycosyl prolines. Few of the proline esters exhibited very good alpha-glucosidase inhibitory activity. The organocatalytic activity of the proline derivatives in a prototype Aldol reaction has also been investigated.

  DOI：

  10.1016/j.bmcl.2006.12.002
• 作为产物：
  描述：

  3-吡啶甲醛 、 甘氨酸乙酯盐酸盐 在 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [(3-pyridyl-methylidene)-amino]-acetic acid ethyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of glycosylated prolines as α-glucosidase inhibitors and organocatalyst in asymmetric aldol reaction

  摘要：

  1,3-Dipolar cycloaddition of azomethine ylides and glycosyl E-olefins in presence of LDA led to diastereoselective formation of C-glycosylated proline esters. The selected esters on regioselective hydrolysis with LiOH gave C-glycosyl prolines. Few of the proline esters exhibited very good alpha-glucosidase inhibitory activity. The organocatalytic activity of the proline derivatives in a prototype Aldol reaction has also been investigated.

  DOI：

  10.1016/j.bmcl.2006.12.002

文献信息

• Ligand-Controlled Diastereoselective 1,3-Dipolar Cycloadditions of Azomethine Ylides with Methacrylonitrile
  作者：Mary C. Walton、Yun-Fang Yang、Xin Hong、K. N. Houk、Larry E. Overman

  DOI：10.1021/acs.orglett.5b03171

  日期：2015.12.18

  glycine ester arylimines and methacrylonitrile provide selective access to either the endo or exo pyrrolidine cycloadducts. DFT calculations have elucidated the origins of ligand-controlled diastereoselectivity.

  铜催化的甘氨酸酯芳烃和甲基丙烯腈的反应提供了对内或外吡咯烷环加合物的选择性通道。DFT计算已阐明了配体控制的非对映选择性的起源。
• Synthesis of enantiomerically pure pyrrolidines by stereospecific cycloaddition of azomethine ylides with enones
  作者：M. Pätzel、G. Galley、P.G. Jones、A. Chrapkowsky

  DOI：10.1016/s0040-4039(00)73839-1

  日期：1993.9

  alkoxy or amino substituent in γ-position react with azomethine ylides 3 (obtained from glycine imines) in the presence of DBU/AgOAc giving enantiomerically pure pyrrolidine derivatives 4 in a stereospecific manner.

  在DBU / AgOAc的存在下，几种在γ位带有手性烷氧基或氨基取代基的（E）-α，β-不饱和酮（烯酮）2与偶氮甲亚胺3（由甘氨酸亚胺获得）反应，得到对映体纯的吡咯烷衍生物4以立体定向的方式。
• Polyfunctionalized Pyrrolidines by Stereoselective 1,3-Dipolar Cycloaddition of Azomethine Ylides to Chiral Enones
  作者：Guido Galley、Juergen Liebscher、Michael Paetzel

  DOI：10.1021/jo00121a019

  日期：1995.8

  The cycloaddition reactions of chiral alpha,beta-unsaturated ketones substituted by alkoxy or amino groups in the gamma-position to azomethine ylides (obtained from glycine imines) were investigated in the presence of a base, LiBr and AgOAc. High regioselectivities were observed in most cases, resulting in the formation of a single diastereomer, particularly if a DBU/AgOAc catalyst system was employed. The influence of reaction conditions and olefin structure on the stereoselectivity of the reaction was investigated, and models rationalizing stereocontrol are proposed. In addition, an interesting deconjugation reaction of acetals derived from gamma,delta-dihydroxy alpha,beta-unsaturated enones or esters is described.
• US4256761A
  申请人：——

  公开号：US4256761A

  公开（公告）日：1981-03-17
• US4304771A
  申请人：——

  公开号：US4304771A

  公开（公告）日：1981-12-08