(2RS,4SR)/(2RS/4RS)-2-Amino-2-methyl-4-phenylpentanenitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2RS,4SR)/(2RS/4RS)-2-Amino-2-methyl-4-phenylpentanenitrile
• 英文别名: 2-amino-2-methyl-4-phenylpentanenitrile
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: FWKITMCSWVMMFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.81
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2RS,4SR)/(2RS/4RS)-2-Amino-2-methyl-4-phenylpentanenitrile 在 盐酸 、 氯化亚砜 、 磺酰氯 、 次氯酸叔丁酯 、 sodium methylate 作用下， 以 正戊烷 为溶剂， 反应 49.75h， 生成 Dimethyl (2R,2'S,4R,4'S)-2,2'-dimethyl-4,4'-diphenyl-2,2'-azopentanoate
  参考文献：
  名称：

  Synthesis of precursors to model styrene/methyl methacrylate copolymer radicals. .alpha.,.alpha.'-Bis(methoxycarbonyl)azoalkanes

  摘要：

  Several symmetrical alpha,alpha'-bis(methoxycarbonyl)azoalkanes 4 were prepared in high yield in two steps from the appropriate alpha-amino esters 13, or in five steps from 4-substituted 4-phenyl-2-butanones 10. The sequence involves the generation, separation, and purification of symmetrical N,N'-disubstituted sulfamides 14 followed by oxidative rearrangement under modified Ohme-Schmitz-Preuschhof conditions to yield the title compounds. In the absence of the oxidant, the sulfamides are converted quantitatively into 2,4-disubstituted 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides 15. In accord with the above methodology, (4S)-4-phenyl-2-pentanone was transformed into (2R,2'R,4S,4'S)-2,2'-bis(methoxycarbonyl)-4,4'-diphenyl-2,2'-azopentane (4b-Ia), the stereochemistry of which was established from that of its precursor (2R,2'R,4S,4'S)-N,N'-bis[2-[2-(methoxycarbonyl)-4-phenylpentyl]]-sulfamide by single-crystal X-ray analysis.

  DOI：

  10.1021/jo00006a014
• 作为产物：
  描述：

  氢氰酸 、 4-苯基戊烷-2-酮 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2RS,4SR)/(2RS/4RS)-2-Amino-2-methyl-4-phenylpentanenitrile
  参考文献：
  名称：

  Synthesis of precursors to model styrene/methyl methacrylate copolymer radicals. .alpha.,.alpha.'-Bis(methoxycarbonyl)azoalkanes

  摘要：

  Several symmetrical alpha,alpha'-bis(methoxycarbonyl)azoalkanes 4 were prepared in high yield in two steps from the appropriate alpha-amino esters 13, or in five steps from 4-substituted 4-phenyl-2-butanones 10. The sequence involves the generation, separation, and purification of symmetrical N,N'-disubstituted sulfamides 14 followed by oxidative rearrangement under modified Ohme-Schmitz-Preuschhof conditions to yield the title compounds. In the absence of the oxidant, the sulfamides are converted quantitatively into 2,4-disubstituted 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides 15. In accord with the above methodology, (4S)-4-phenyl-2-pentanone was transformed into (2R,2'R,4S,4'S)-2,2'-bis(methoxycarbonyl)-4,4'-diphenyl-2,2'-azopentane (4b-Ia), the stereochemistry of which was established from that of its precursor (2R,2'R,4S,4'S)-N,N'-bis[2-[2-(methoxycarbonyl)-4-phenylpentyl]]-sulfamide by single-crystal X-ray analysis.

  DOI：

  10.1021/jo00006a014

文献信息

• DANEK, STEFAN K.;KELLY, DAVID P.;STEEL, PETER J., J. ORG. CHEM., 56,(1991) N, C. 2031-2039
  作者：DANEK, STEFAN K.、KELLY, DAVID P.、STEEL, PETER J.

  DOI：——

  日期：——
• Synthesis of precursors to model styrene/methyl methacrylate copolymer radicals. .alpha.,.alpha.'-Bis(methoxycarbonyl)azoalkanes
  作者：Stefan K. Danek、David P. Kelly、Peter J. Steel

  DOI：10.1021/jo00006a014

  日期：1991.3

  Several symmetrical alpha,alpha'-bis(methoxycarbonyl)azoalkanes 4 were prepared in high yield in two steps from the appropriate alpha-amino esters 13, or in five steps from 4-substituted 4-phenyl-2-butanones 10. The sequence involves the generation, separation, and purification of symmetrical N,N'-disubstituted sulfamides 14 followed by oxidative rearrangement under modified Ohme-Schmitz-Preuschhof conditions to yield the title compounds. In the absence of the oxidant, the sulfamides are converted quantitatively into 2,4-disubstituted 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides 15. In accord with the above methodology, (4S)-4-phenyl-2-pentanone was transformed into (2R,2'R,4S,4'S)-2,2'-bis(methoxycarbonyl)-4,4'-diphenyl-2,2'-azopentane (4b-Ia), the stereochemistry of which was established from that of its precursor (2R,2'R,4S,4'S)-N,N'-bis[2-[2-(methoxycarbonyl)-4-phenylpentyl]]-sulfamide by single-crystal X-ray analysis.