ethyl 2-acetyl-N-alaninante | 185450-24-2

• 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: ethyl 2-acetyl-N-alaninante
• 英文别名: Ethyl 2-[bis(methylsulfanyl)methylideneamino]-2-methyl-3-oxobutanoate
• CAS: 185450-24-2
• 化学式: C₁₀H₁₇NO₃S₂
• 分子量: 263.382
• InChiKey: SMKDWKPJWFUVSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetyl-N-alaninante 在 异氰基乙酸乙酯 、 lithium tert-butoxide 作用下， 以 乙醇 、 水 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 20.25h， 生成
  参考文献：
  名称：

  Diastereoselective synthesis of functionalized 2,4-diamino-3-hydroxyglutaric acid derivatives of potential biological interest from glycine derivatives

  摘要：

  Two out of the four possible diastereomers of C- and N-protected 2,4-diamino-3-hydroxyglutaric acid derivatives 6a-c were obtained with diastereomeric excesses of 9:1 to 1:1. The compound 6b was converted into two lactam derivatives of 2,4-di(N-methylamino)-3-hydroxy-3-phenylglutaric acid diethyl ester with retention of configuration.

  DOI：

  10.1016/s0040-4039(00)73935-9
• 作为产物：
  描述：

  ethyl N-alaninate 、 乙酰氯 在 potassium tert-butylate 作用下， 生成 ethyl 2-acetyl-N-alaninante
  参考文献：
  名称：

  N- [双（甲硫基）亚甲基]甘氨酸乙酯与N- [双（甲硫基）亚甲基]苄胺衍生的氮杂烯丙基碳负离子的酰化反应

  摘要：

  已经研究了衍生自1和2的氮杂烯丙基阴离子的酰化反应的新方面。在合适的反应条件下，可以制备恶唑5，α，α-二取代的α-酰基-α-氨基酸衍生物3和α，β-二氢化氢氨基酸衍生物7。通过原位加成-环缩合串联反应，衍生自N- [双（甲硫基亚甲基）亚甲基苄胺2的C-酰基中间体与阴离子2反应，分离出新的1,3-二氨基-2-丙醇衍生物8。

  DOI：

  10.1016/s0040-4020(97)00091-4

文献信息

• Diastereoselective Synthesis of α,α-Disubstituted γ-Carboxypyroglutamates <i>via</i> Sm(III)−Azomethine Ylide Cycloadditions
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csákÿ、Isabel López de Silanes、M. Luz Quiroga

  DOI：10.1021/jo961418b

  日期：1997.2.1

  Sm(III)-azomethine ylides 2 have been generated from ketones 1. Cycloaddition of ylides 2 with alpha,beta-unsaturated esters 3 through a transition state chelation-controlled by the metal allowed for the asymmetric synthesis of gamma-carboxypyroglutamates having a quaternary alpha-carbon that are potentially useful in the synthesis of neuroprotective agents.

  已从酮1生成Sm（III）-偶氮甲亚胺基化物2。通过金属控制的过渡态螯合，将基化物2与α，β-不饱和酯3进行环加成反应，从而可以不对称合成具有季位α的γ-羧基焦谷氨酸。 -碳可能在合成神经保护剂中有用。
• Diastereoselective 1,3-dipolar cycloaddition of Sm(III)-azomethine ylides to α,β-unsaturated esters
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csákÿ、M. Martínez、M.Luz Quiroga

  DOI：10.1016/0040-4039(96)01402-5

  日期：1996.9

  Sm(III)-Azomethine ylides were generated by fragmentation of the iminodithiocarbonates 1 with SmI2 in THF. 1,3-Dipolar cycloaddition of these species with α,β-unsaturated esters 3 afforded the highly functionalized 2-methylthio-Δ1-pyrrolines 4 with good yields and diastereoselectivities.

  通过在THF中用SmI 2裂解亚氨基二硫代碳酸酯1来生成Sm（III）-偶氮甲亚胺。这些物种与α，β不饱和酯的1,3-偶极环加成3得到高度官能2-甲硫基Δ 1 -pyrrolines 4具有良好的产率和非对映选择性。
• Diastereoselective reduction of α-acyl-N-[Bis(methylthio)methylene]alaninates and phenylalaninates: Synthesis of α,α-disubstituted β-hydroxy α-amino esters
  作者：Carlos Alvarez-Ibarra、Aurelio G Csákÿ、M Luz Quiroga、Dolores Ramírez

  DOI：10.1016/s0040-4020(96)01121-0

  日期：1997.2

  Chemoselective reduction of the carbonyl group in α-acyl-N-[Bis(methylthio)methylene]-alaninates 1a-c and phenylalaninates 1d,e allowed for the diastereoselective synthesis of both the syn and the anti isomers of the corresponding N-protected α,α-disubstituted β-hydroxy-α-amino esters 2. The stereochemistry of the process was tuned by switching between chelation-controlled and non-chelation-controlled

  在α-酰基-N- [双（甲硫基）亚甲基] -alaninates羰基的化学选择性还原1A-1C和phenylalaninates 1d的，例如允许的顺式和相应的N-保护的α的反式异构体两者的非对映选择性合成，α-二取代的β-羟基-α-氨基酯2。通过在螯合控制和非螯合控制的条件之间进行切换来调节该过程的立体化学。化合物2可以转化为相应的N-未保护的α-季铵化的β-羟基-α-氨基酯4。
• Diastereoselective synthesis of syn,syn- and syn,anti-2,4-diamino-3-hydroxyglutaric acid derivatives from ethyl α-acyl alaninates
  作者：Carlos Alvarez-Ibarra、Aurelio G Csákÿ、Elena Martínez-Santos、Maria L Quiroga、JoséL Tejedor

  DOI：10.1016/s0040-4020(99)00065-4

  日期：1999.3

  Syn,syn- and syn,anti-isomers of the four possible diastereomers of O,N,N'-protected 2,4-diamino-3-hydroxyglutaric acid derivatives 3-7 were diastereoselectively obtained. Syn,syn isomers of oxazolines 3 were selectively achieved by an aldol-like reaction in protic conditions between a-metallated ethyl isocyanoacetate 1 and alpha-acyl alaninates 2. Derivatives 4 with a syn,anti-configuration were obtained under epimerization reaction conditions, whereas derivatives 5-7 with syn,syn-configuration were selectively obtained under kinetic reaction conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.