(R)-diethyl 1-hydroxy-3-methylbutylphosphonate | 141207-35-4

• 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: (R)-diethyl 1-hydroxy-3-methylbutylphosphonate
• 英文别名: (1R)-1-diethoxyphosphoryl-3-methylbutan-1-ol
• CAS: 141207-35-4
• 化学式: C₉H₂₁O₄P
• 分子量: 224.237
• InChiKey: KGWVUOHVWZFPTK-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-diethyl 1-hydroxy-3-methylbutylphosphonate 在 palladium on activated charcoal 盐酸 、 二苯基膦叠氮化物 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 (S)-1-磷-3-甲基丁胺
  参考文献：
  名称：

  Enantioselective synthesis of α-amino phosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphite

  摘要：

  Stereoselective opening of homochiral acetals (2a-c) with triethyl phosphite was applied to the enantioselective synthesis of phosphono alcohols (1a-c), which were successfully converted to the alpha-amino phosphonic acid diethyl esters (6a-c).

  DOI：

  10.1016/s0957-4166(00)80280-3
• 作为产物：
  描述：

  [(R)-1-((1S,3S)-3-Hydroxy-1-methyl-butoxy)-3-methyl-butyl]-phosphonic acid diethyl ester 在 对甲苯磺酸 、 二甲基亚砜 作用下， 生成 (R)-diethyl 1-hydroxy-3-methylbutylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of α-amino phosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphite

  摘要：

  Stereoselective opening of homochiral acetals (2a-c) with triethyl phosphite was applied to the enantioselective synthesis of phosphono alcohols (1a-c), which were successfully converted to the alpha-amino phosphonic acid diethyl esters (6a-c).

  DOI：

  10.1016/s0957-4166(00)80280-3

文献信息

• Nonenzymatic kinetic resolution of racemic α-hydroxyalkanephosphonates with chiral copper catalyst
  作者：Yosuke Demizu、Atsushi Moriyama、Osamu Onomura

  DOI：10.1016/j.tetlet.2009.07.003

  日期：2009.9

  Kinetic resolution of alpha-hydroxyalkanephosphonates was efficiently performed by benzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with excellent s value of up to 286. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl α-ketophosphonates
  作者：Tadeusz Gajda

  DOI：10.1016/s0957-4166(00)86271-0

  日期：1994.10

  Reduction of diethyl alpha-ketophosphonates 1 with borane and B-butyloxazaborolidine 2 as catalyst afforded diethyl (S)- or (R)-1-hydroxyalkylphosphonates 3a-d or 3e-f respectively in good yields and moderate to good enantiomeric excess (53-83 ee%). Respective diethyl (R)- and (S)-1-aminoalkylphosphonates 6 were obtained in a one-pot transformation, by the Mitsunobu reaction of 1-hydroxyphosphonates 3 with hydrazoic acid, and subsequent treatment of the intermediate azides 4, with triphenylphosphine, followed by hydrolysis df the iminophosphoranes 5 with water.
• Enantioselective synthesis of α-amino phosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphite
  作者：Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1016/s0957-4166(00)80280-3

  日期：1992.1

  Stereoselective opening of homochiral acetals (2a-c) with triethyl phosphite was applied to the enantioselective synthesis of phosphono alcohols (1a-c), which were successfully converted to the alpha-amino phosphonic acid diethyl esters (6a-c).