(R)-alpha-氨基环己-1,4-二烯-1-乙酰氯盐酸盐

• 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
• 中文名称: (R)-alpha-氨基环己-1,4-二烯-1-乙酰氯盐酸盐
• 英文名称: 2-(R)-(1,4-Cyclohexadienyl)glycyl hydrochloride
• 英文别名: (2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl chloride;hydron;chloride
• 化学式: C₈H₁₀ClNO*ClH
• 分子量: 208.087
• InChiKey: DLDIEAJVIRFDHY-OGFXRTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R)-alpha-氨基环己-1,4-二烯-1-乙酰氯盐酸盐 反应 1.0h， 以93%的产率得到D-双氧苯甘酸甲酯
  参考文献：
  名称：

  Asymmetric Synthesis of .beta.-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using .alpha.-Amino Esters as the Chiral Auxiliary

  摘要：

  Imine esters of glycine, (R)-phenylglycine, (R)-(1,4-cyclohexadienyl)glycine and (S)-valine have been employed in the ester enolate-imine condensation via double activation with ZnCl2. The reaction of the chlorozinc enolate (1b) of ethyl (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)acetate with (R)-methyl N-benzylidene-2-phenylglycinate (2a) afforded the trans-beta-lactam 3a in 79% yield with excellent asymmetric induction (de >97%). Other imine esters also afforded trans-beta-lactams diastereoselectively, albeit in lower conversions (37-70%). Methyl (S)-2-[N-[3-(trimethylsilyl)-2-propyn-1-ylidene]amino]-3-methylbutanoate (2e) afforded a mixture of four diastereoisomers (68% conversion). The products were isolated as 3-phthalimido beta-lactams 5b-e and as 3-[(methoxycarbonyl)amino]-beta-lactam 6b. The reactivity of the zinc enolates and the diastereoselectivity of the reactions are discussed in terms of the coordination of the imine esters to ZnCl2 (template effect) and the stability and aggregation equilibria of the zinc enolates.

  DOI：

  10.1021/jo00119a009

文献信息

• FALCIANI, M.;BROGGI, R.
  作者：FALCIANI, M.、BROGGI, R.

  DOI：——

  日期：——