[(E)-(R)-2-Methoxy-1-phenyl-ethylimino]-acetic acid ethyl ester | 110361-97-2

• 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: [(E)-(R)-2-Methoxy-1-phenyl-ethylimino]-acetic acid ethyl ester
• CAS: 110361-97-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: INNLCAJDJXMHIZ-IGVUGNCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bromozinc(1+),2-methylpropane 、 [(E)-(R)-2-Methoxy-1-phenyl-ethylimino]-acetic acid ethyl ester 在 zinc dibromide 、 氯化铵 作用下， 以 乙醚 、 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以68%的产率得到2-((R)-2-Methoxy-1-phenyl-ethylamino)-3,3-dimethyl-butyric acid ethyl ester
  参考文献：
  名称：

  Diastereoselective addition of organozinc reagents to chiral α-imino esters

  摘要：

  The addition of organozinc reagents to chiral a-imino esters pre-complexed with zinc bromide, occurred with complete regioselectivity at the imino carbon. The influence of the solvent, temperature and different chiral auxiliaries was studied. The best diastereoselectivities were obtained in Et2O or CH2Cl2 at 0degreesC, using phenylglycinol methyl ether as the chiral inductor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00587-6
• 作为产物：
  描述：

  苯乙醇,b-[(苯基亚甲基)氨基]-,(R)- 在 sodium hydride 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 [(E)-(R)-2-Methoxy-1-phenyl-ethylimino]-acetic acid ethyl ester
  参考文献：
  名称：

  Diastereoselective addition of organozinc reagents to chiral α-imino esters

  摘要：

  The addition of organozinc reagents to chiral a-imino esters pre-complexed with zinc bromide, occurred with complete regioselectivity at the imino carbon. The influence of the solvent, temperature and different chiral auxiliaries was studied. The best diastereoselectivities were obtained in Et2O or CH2Cl2 at 0degreesC, using phenylglycinol methyl ether as the chiral inductor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00587-6

文献信息

• The Asymmetric Addition of the Sn(II) Enolates of Thioesters to α-Iminoesters. A Convenient Synthesis of Optically Active cis-Substituted β-Lactams.
  作者：Tohru Yamada、Hiroshi Suzuki、Teruaki Mukaiyama

  DOI：10.1246/cl.1987.293

  日期：1987.2.5

  The asymmetric addition of the Sn(II) enolates derived from thioesters to α-iminoesters having the chiral auxiliary on the nitrogen atom proceeds smoothly to afford syn-β-aminoacid derivatives, which are in turn converted to optically active cis-substituted β-lactams.

  由硫酯衍生的 Sn(II) 烯醇化物与在氮原子上具有手性助剂的 α-亚氨基酯的不对称加成顺利进行，得到顺-β-氨基酸衍生物，然后将其转化为具有旋光活性的顺式取代 β-内酰胺.