(RS)-(3-tert-butoxycarbonylamino-2-oxo-butyl)phosphonic acid dimethyl ester | 112457-20-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (RS)-(3-tert-butoxycarbonylamino-2-oxo-butyl)phosphonic acid dimethyl ester
• 英文别名: tert-butyl N-(4-dimethoxyphosphoryl-3-oxobutan-2-yl)carbamate
• CAS: 112457-20-2
• 化学式: C₁₁H₂₂NO₆P
• 分子量: 295.273
• InChiKey: ZMEXPPSINVRMAD-UHFFFAOYSA-N

物化性质

• 沸点：
  399.4±27.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (RS)-(3-tert-butoxycarbonylamino-2-oxo-butyl)phosphonic acid dimethyl ester 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.25h， 生成 trans-(RS)-2-acetamido-5-phenyl-4-penten-3-one
  参考文献：
  名称：

  Functionalized amido ketones: new anticonvulsant agents

  摘要：

  We have reported that functionalized amino acids (FAA) are potent anticonvulsants. Replacing the N-terminal amide group in FAA with phenethyl, styryl, and phenylethynyl units provided a series of functionalized amido ketones (FAK). We show that select FAK exhibit significant anticonvulsant activities thereby providing information about the structural requirements for FAA and FAK bioactivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00434-6
• 作为产物：
  描述：

  methyl 2-(tert-butoxycarbonylamino)propanoate 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以83%的产率得到(RS)-(3-tert-butoxycarbonylamino-2-oxo-butyl)phosphonic acid dimethyl ester
  参考文献：
  名称：

  Functionalized amido ketones: new anticonvulsant agents

  摘要：

  We have reported that functionalized amino acids (FAA) are potent anticonvulsants. Replacing the N-terminal amide group in FAA with phenethyl, styryl, and phenylethynyl units provided a series of functionalized amido ketones (FAK). We show that select FAK exhibit significant anticonvulsant activities thereby providing information about the structural requirements for FAA and FAK bioactivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00434-6

文献信息

• Improved syntheses of α-BOC-aminoketones from α-BOC-amino-Weinreb amides using a pre-deprotonation protocol
  作者：Jinchu Liu、Norihiro Ikemoto、Daniel Petrillo、Joseph D. Armstrong

  DOI：10.1016/s0040-4039(02)02031-2

  日期：2002.11

  A general procedure was developed to prepare alpha-BOC-aminoketones in good yields from alpha-BOC-amino Weinreb amides containing an exchangeable amino proton. By first deprotonating this amino group using 1 equiv. of a simple alkyl Grignard base, only a stoichiometric amount, rather than a large excess, of the nucleophile was needed to prepare the ketone. This procedure is therefore more economical to run and the purification is easier. (C) 2002 Elsevier Science Ltd. All rights reserved.
• CHAKRAVARTY P. K.; COMBS P.; ROTH A.; GREENLEE W. J., TETRAHEDRON LETT., 28,(1987) N 6, 611-612
  作者：CHAKRAVARTY P. K.、 COMBS P.、 ROTH A.、 GREENLEE W. J.

  DOI：——

  日期：——
• Functionalized amido ketones: new anticonvulsant agents
  作者：C BEGUIN

  DOI：10.1016/s0968-0896(03)00434-6

  日期：2003.9

  We have reported that functionalized amino acids (FAA) are potent anticonvulsants. Replacing the N-terminal amide group in FAA with phenethyl, styryl, and phenylethynyl units provided a series of functionalized amido ketones (FAK). We show that select FAK exhibit significant anticonvulsant activities thereby providing information about the structural requirements for FAA and FAK bioactivity. (C) 2003 Elsevier Ltd. All rights reserved.