dimethyl (R,R)-(+)-3-N,N-bis(α-methylbenzyl)-amino-2-oxopropylphosphonate | 787629-78-1

• 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: dimethyl (R,R)-(+)-3-N,N-bis(α-methylbenzyl)-amino-2-oxopropylphosphonate
• 英文别名: 1-[bis[(1R)-1-phenylethyl]amino]-3-dimethoxyphosphorylpropan-2-one
• CAS: 787629-78-1
• 化学式: C₂₁H₂₈NO₄P
• 分子量: 389.431
• InChiKey: OIRWKOHWXRISQZ-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (R,R)-(+)-3-N,N-bis(α-methylbenzyl)-amino-2-oxopropylphosphonate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 dimethyl 3-[(R,R)-N,N-bis(α-methylbenzylamino)]-(2R)-hydroxypropylphosphonate 、 dimethyl 3-[(R,R)-N,N-bis(α-methylbenzylamino)]-(2S)-hydroxypropylphosphonate
  参考文献：
  名称：

  Highly diastereoselective reduction of β-ketophosphonates bearing homochiral bis(α-methylbenzyl)amine: preparation of both enantiomers of phosphogabob (GABOBP)

  摘要：

  The reduction of dimethyl 3-N,N-di(alpha-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane at -78degreesC in presence of LiClO4, gave gamma-amino-beta-hydroxyphosphonates 10 and 11 in good yield and with excellent diastereoselectivity. This procedure represents an example of highly diastereoselective 1,4-induction. The hydrolysis and hydrogenation of 10 and 11 afforded the (R)- and (S)-gamma-amino-beta-hydroxypropylphosphonic acid (GABOB(P)), respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.033
• 作为产物：
  描述：

  (+)-双[(R)-1-苯乙基]胺 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.5h， 生成 dimethyl (R,R)-(+)-3-N,N-bis(α-methylbenzyl)-amino-2-oxopropylphosphonate
  参考文献：
  名称：

  Highly diastereoselective reduction of β-ketophosphonates bearing homochiral bis(α-methylbenzyl)amine: preparation of both enantiomers of phosphogabob (GABOBP)

  摘要：

  The reduction of dimethyl 3-N,N-di(alpha-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane at -78degreesC in presence of LiClO4, gave gamma-amino-beta-hydroxyphosphonates 10 and 11 in good yield and with excellent diastereoselectivity. This procedure represents an example of highly diastereoselective 1,4-induction. The hydrolysis and hydrogenation of 10 and 11 afforded the (R)- and (S)-gamma-amino-beta-hydroxypropylphosphonic acid (GABOB(P)), respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.033