(2S*,1'R*)-dimethyl 2-[1-[diphenyl(N-methoxycarbonyl)phosphoranyl]-ethyl]-butanedioate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S*,1'R*)-dimethyl 2-[1-[diphenyl(N-methoxycarbonyl)phosphoranyl]-ethyl]-butanedioate
• 英文别名: dimethyl (2S)-2-[(1R)-1-[methoxycarbonylimino(diphenyl)-lambda5-phosphanyl]ethyl]butanedioate；dimethyl (2S)-2-[(1R)-1-[methoxycarbonylimino(diphenyl)-λ5-phosphanyl]ethyl]butanedioate
• 化学式: C₂₂H₂₆NO₆P
• 分子量: 431.425
• InChiKey: KYQZLBRNFIOLTC-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙基二苯基膦 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.5h， 生成 (2S*,1'R*)-dimethyl 2-[1-[diphenyl(N-methoxycarbonyl)phosphoranyl]-ethyl]-butanedioate
  参考文献：
  名称：

  Reactions of lithiated P -diphenyl(alkyl)( N -methoxycarbonyl)phosphazenes with Michael acceptors and aldehydes. Synthesis of 1 H -1,2-azaphosphinin-6-ones, β-hydroxy( N -methoxycarbonyl)phosphazenes and 5,6-dihydro-1,3,4-oxazaphosphinin-2-ones

  摘要：

  Lithium (N-methoxycarbonyl)phosphazenes add C-regioselectively to DMAD, dimethyl malonate, fumarate, and butyl idenmalonate in a [1,4] manner. Only one diastereoisomer is observed with the olefinic electrophiles. With DMAD the initial adduct evolves through cyclocondensation with the CO2Me group of the phosphazene and 1H-1,2-azaphosphinin-6-ones are obtained. Exceptionally, methyl phenylpropiolate reacted exclusively through the carbonyl yielding a mixture of C- and N-acylated compounds. The addition to aldehydes at -80 degreesC affords beta -hydroxyphosphazenes diastereoselectively. For lithium oc,bi-dimethyl(N-methoxycarbonyl)phospha the intermediate all;oxides cyclocondense at room temperature to 5,6-dihydro-1,3,4-oxazaphosphinin-2-ones. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00165-x

文献信息

• Reactions of lithiated P -diphenyl(alkyl)( N -methoxycarbonyl)phosphazenes with Michael acceptors and aldehydes. Synthesis of 1 H -1,2-azaphosphinin-6-ones, β-hydroxy( N -methoxycarbonyl)phosphazenes and 5,6-dihydro-1,3,4-oxazaphosphinin-2-ones
  作者：Julia M Álvarez-Gutiérrez、Emma Peralta-Pérez、Isidro Pérez-Álvarez、Fernando López-Ortiz

  DOI：10.1016/s0040-4020(01)00165-x

  日期：2001.4

  Lithium (N-methoxycarbonyl)phosphazenes add C-regioselectively to DMAD, dimethyl malonate, fumarate, and butyl idenmalonate in a [1,4] manner. Only one diastereoisomer is observed with the olefinic electrophiles. With DMAD the initial adduct evolves through cyclocondensation with the CO2Me group of the phosphazene and 1H-1,2-azaphosphinin-6-ones are obtained. Exceptionally, methyl phenylpropiolate reacted exclusively through the carbonyl yielding a mixture of C- and N-acylated compounds. The addition to aldehydes at -80 degreesC affords beta -hydroxyphosphazenes diastereoselectively. For lithium oc,bi-dimethyl(N-methoxycarbonyl)phospha the intermediate all;oxides cyclocondense at room temperature to 5,6-dihydro-1,3,4-oxazaphosphinin-2-ones. (C) 2001 Elsevier Science Ltd. All rights reserved.