(R)-6-Amino-5-cyano-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-4H-pyran-3-carboxylic acid ethyl ester | 143264-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-6-Amino-5-cyano-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-4H-pyran-3-carboxylic acid ethyl ester
• 英文别名: ethyl (4R)-6-amino-5-cyano-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenyl-4H-pyran-3-carboxylate
• CAS: 143264-83-9
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: MBNOQSNVFFZJLB-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 哌啶 sodium periodate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 27.5h， 生成 (R)-6-Amino-5-cyano-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-4H-pyran-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Michael addition of malononitrile to chiral α-acylacrylates

  摘要：

  Starting from 2,3-0-isopropylidene-D-glyceraldehyde (1), 3-O-methyl and 3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose (4a, 4b), we describe the synthesis of the alpha-acyl-beta-alkyl substituted acrylates 2 and 5. The Michael addition of malononitrile to these substrates gives the polyfunctionalized 2-amino-4H-pyrans 3 and 6 with moderate diastereoselectivity and reasonable overall yield from diols 7 and 8a,b. A detailed analysis is performed scanning different type of bases in the Michael reaction. We find that, while for acceptor 2 no changes are observed, for compound 5 the stereochemical outcome of the 1,4-addition is reversed in going from piperidine, sodium hydride or potassium t-butoxide to lithium diisopropylamide or lithium diisopropylamide/magnesium iodide reagent. Several models for rationalising the results are proposed.

  DOI：

  10.1016/s0040-4020(01)87984-9

文献信息

• The first asymmetric synthesis of polyfunctionalized 4H-pyrans via Michael addition of malononitrile to 2-acyl acrylates
  作者：Rafael González、Nazario Martín、Carlos Seoane、JoséL Marco、Armando Albert、Félix H Cano

  DOI：10.1016/0040-4039(92)80031-e

  日期：1992.6

  Starting from (R)-2,3-O-isopropylideneglyceraldehyde, the first asymmetric synthesis of 4H-pyrans (4BAR) has been developed; a de tailed X-ray structural and stereochemical study has established as R the absolute configuration at the new stereocenter in compounds 4.
• Michael addition of malononitrile to chiral α-acylacrylates
  作者：José L. Marco、Gemma Martín、Nazario Martín、Angeles Martínez-Grau、Carlos Seoane、Armando Albert、Félix H. Cano

  DOI：10.1016/s0040-4020(01)87984-9

  日期：1993.8

  Starting from 2,3-0-isopropylidene-D-glyceraldehyde (1), 3-O-methyl and 3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose (4a, 4b), we describe the synthesis of the alpha-acyl-beta-alkyl substituted acrylates 2 and 5. The Michael addition of malononitrile to these substrates gives the polyfunctionalized 2-amino-4H-pyrans 3 and 6 with moderate diastereoselectivity and reasonable overall yield from diols 7 and 8a,b. A detailed analysis is performed scanning different type of bases in the Michael reaction. We find that, while for acceptor 2 no changes are observed, for compound 5 the stereochemical outcome of the 1,4-addition is reversed in going from piperidine, sodium hydride or potassium t-butoxide to lithium diisopropylamide or lithium diisopropylamide/magnesium iodide reagent. Several models for rationalising the results are proposed.