4-tert-butyl 1-ethyl 2-(4-methoxyphenylamino)succinate

• 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: 4-tert-butyl 1-ethyl 2-(4-methoxyphenylamino)succinate
• 英文别名: 4-O-tert-butyl 1-O-ethyl 2-(4-methoxyanilino)butanedioate
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: BEOLYIKFECZAII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (4-methoxyphenylimino)acetate 、 (2-tert-butoxy-2-oxoethyl)zinc(II) bromide 以 四氢呋喃 为溶剂， 以82%的产率得到4-tert-butyl 1-ethyl 2-(4-methoxyphenylamino)succinate
  参考文献：
  名称：

  An efficient synthesis of N-arylated, orthogonally protected racemic aspartates

  摘要：

  A brief and efficient synthesis of variously N-arylated racemic aspartates has been achieved by two consecutive reactions in one-pot, in which imine or equivalent, formed in situ from various anilines and ethyl glyoxylate, reacted with the Reformatsky reagent, tert-butyl 2-bromozinc acetate. Notably the two esters are orthogonally protected for the convenience of further derivatization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.060

文献信息

• Chelation-controlled diastereoselective construction of N-aryl-, N-acyl/tosylhydrazono β-substituted aspartate derivatives via Barbier-type reaction
  作者：Nayyar Ahmad Aslam、Srinivasarao Arulananda Babu、Arya Jayadev Sudha、Makoto Yasuda、Akio Baba

  DOI：10.1016/j.tet.2013.05.130

  日期：2013.8

  involvement of a chelation-controlled TS. The synthesis of functionalized 1,4-diols, cis piperidine-2,3-dicarboxylate derivative and β-ethyl aspartic acid hydrochloride was performed using the N-substituted β-vinyl aspartates obtained in this work. The stereochemistry of representative products was unambiguously established from the single crystal X-ray structure analyses.

  通过铟介导的4-溴巴豆酸烷基酯或α-卤代酯与N-芳基的铟介导的Barbier型加成反应，进入几种具有两个连续立体中心的N-取代-β-乙烯基天冬氨酸和β-烷基天冬氨酸烷基酯衍生物的立体选择性合成包括N -PMP）的α-亚氨基-和N-酰基/甲苯磺酰hydr酯。仅在醇介质中具有顺式立体化学的β-烷基天冬氨酸衍生物的形成揭示了螯合控制的TS的参与。使用N进行官能化的1,4-二醇，顺式哌啶-2,3-二羧酸酯衍生物和β-乙基天冬氨酸盐酸盐的合成在这项工作中获得的取代的β-乙烯基天冬氨酸盐。从单晶X射线结构分析明确确定了代表性产品的立体化学。
• An efficient synthesis of N-arylated, orthogonally protected racemic aspartates
  作者：Guanglin Luo、Ling Chen、Rita Civiello、Gene M. Dubowchik

  DOI：10.1016/j.tetlet.2007.11.060

  日期：2008.1

  A brief and efficient synthesis of variously N-arylated racemic aspartates has been achieved by two consecutive reactions in one-pot, in which imine or equivalent, formed in situ from various anilines and ethyl glyoxylate, reacted with the Reformatsky reagent, tert-butyl 2-bromozinc acetate. Notably the two esters are orthogonally protected for the convenience of further derivatization. (c) 2007 Elsevier Ltd. All rights reserved.