dimethyl (S)-[1-(N-acetylamino)-2-oxo-1-{(E)-3-phenyl-2-propenyl}propyl]phosphonate | 245366-66-9

• 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: dimethyl (S)-[1-(N-acetylamino)-2-oxo-1-{(E)-3-phenyl-2-propenyl}propyl]phosphonate
• 英文别名: N-[(E,3S)-3-dimethoxyphosphoryl-2-oxo-6-phenylhex-5-en-3-yl]acetamide
• CAS: 245366-66-9
• 化学式: C₁₆H₂₂NO₅P
• 分子量: 339.328
• InChiKey: RYGOWGMWJDDDKP-KXKDPZRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (S)-[1-(N-acetylamino)-2-oxo-1-{(E)-3-phenyl-2-propenyl}propyl]phosphonate 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  Enantioselective Construction of Quaternary α-Carbon Centers on α-Amino Phosphonates via Catalytic Asymmetric Allylation

  摘要：

  [GRAPHICS]Asymmetric allylation of alpha-acetamido beta-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(pi-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding alpha-alkyl alpha-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or BU4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.

  DOI：

  10.1021/ol990679f
• 作为产物：
  描述：

  乙酸肉桂酯 、 dimethyl (1-acetamido-2-oxopropyl)phosphonate 在 [Pd(ϖ-allyl)(cod)]BF4 potassium tert-butylate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 dimethyl (S)-[1-(N-acetylamino)-2-oxo-1-{(E)-3-phenyl-2-propenyl}propyl]phosphonate 、 dimethyl (R)-[1-(N-acetylamino)-2-oxo-1-{(E)-3-phenyl-2-propenyl}propyl]phosphonate
  参考文献：
  名称：

  Enantioselective Construction of Quaternary α-Carbon Centers on α-Amino Phosphonates via Catalytic Asymmetric Allylation

  摘要：

  [GRAPHICS]Asymmetric allylation of alpha-acetamido beta-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(pi-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding alpha-alkyl alpha-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or BU4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.

  DOI：

  10.1021/ol990679f

文献信息

• Enantioselective Construction of Quaternary α-Carbon Centers on α-Amino Phosphonates via Catalytic Asymmetric Allylation
  作者：Ryoichi Kuwano、Ryo Nishio、Yoshihiko Ito

  DOI：10.1021/ol990679f

  日期：1999.9.1

  [GRAPHICS]Asymmetric allylation of alpha-acetamido beta-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(pi-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding alpha-alkyl alpha-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or BU4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.