(S)-(3-chloro-2-hydroxypropyl)phosphonic acid | 900537-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (S)-(3-chloro-2-hydroxypropyl)phosphonic acid
• 英文别名: (2S)-2-hydroxy-3-chloropropylphosphonic acid；(S)-2-hydroxy-3-chloropropylphosphonic acid；[(2S)-3-chloro-2-hydroxypropyl]phosphonic acid
• CAS: 900537-09-9
• 化学式: C₃H₈ClO₄P
• 分子量: 174.521
• InChiKey: MTHUXSANBRAURH-GSVOUGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(3-chloro-2-hydroxypropyl)phosphonic acid 、 三甲胺 以 水 为溶剂， 反应 48.0h， 以46 mg的产率得到(R)-(+)-phosphocarnitine trimethylammonium chloride
  参考文献：
  名称：

  化学酶法合成磷酸肉碱对映体。

  摘要：

  从3-氯-2-氧代丙烷膦酸二乙酯二乙酯开始，分三步合成外消旋磷酸肉碱3，包括将4还原为相应的2-羟基膦酸酯5，将后者转化为膦酸6，最后与三甲胺反应，得到三甲基铵。 3的盐。贝克酵母还原4和酶动力学拆分（+/-）-5，得到对映体纯的磷酸肉碱，（R）-（+）-5和（S）-（-）-5，分别转化为（S）-（-）-和（R）-（+）-磷酸肉碱3。

  DOI：

  10.1021/jo020330x
• 作为产物：
  描述：

  di(1R,2S,5R)-menthyl (S)-2-hydroxy-3-chloropropylphosphonate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以93.5%的产率得到(S)-(3-chloro-2-hydroxypropyl)phosphonic acid
  参考文献：
  名称：

  Di(1R,2S,5R)-menthyl 2-Hydroxy-3-chloropropylphosphonate 作为一种有用的手性合成子，用于制备对映体纯膦酸

  摘要：

  通过二(1R,2S,5R)-薄荷基酮膦酸酯反应合成立体化学纯的二(1R,2S,5R)-薄荷酯(S)-和(R)-2-羟基-3-氯丙基膦酸酯与由硼氢化钠和（R，R）-（+）-酒石酸或与（S，S）-（-）-酒石酸制备的手性配合物。2-羟基-3-氯丙基膦酸二甲酯被用作制备生物活性产品的chiron。

  DOI：

  10.1055/s-2007-985589

文献信息

• Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride
  作者：E.V. Gryshkun、V. Nesterov、O. I. Kolodyazhnyi

  DOI：10.3998/ark.5550190.0013.409

  日期：——

  asymmetric reduction of αand β ketophosphonates using chiral complexes prepared from sodium borohydride and natural aminoacids or tartaric acids was developed. Reduction of α or β ketophosphonates by these reagents led to formation of chiral (S)or (R)hydroxyphosphonates. Reduction of chiral di-(1R,2S,5R)-menthylketophosphonates by the chiral complexes NaBH4/(R,R)-proline or NaBH4/(R,R)-tartaric acid due to

  开发了一种使用由硼氢化钠和天然氨基酸或酒石酸制备的手性配合物不对称还原 α 和 β 酮膦酸酯的方法。这些试剂还原 α 或 β 酮膦酸酯导致手性 (S) 或 (R) 羟基膦酸酯的形成。由于双匹配不对称诱导，手性复合物 NaBH4/(R,R)-脯氨酸或 NaBH4/(R,R)-酒石酸还原手性二-(1R,2S,5R)-薄荷基酮膦酸酯导致立体选择性增加反应并导致羟基膦酸酯的形成高达 90% ee 或更高。使用 2-羟基-3 氯丙基膦酸二甲酯作为制备多克数量的多种生物活性化合物的 chiron。
• Efficient method for the asymmetric reduction of α- and β-ketophosphonates
  作者：V.V. Nesterov、O.I. Kolodiazhnyi

  DOI：10.1016/j.tet.2007.04.101

  日期：2007.7

  versatile method for the asymmetric reduction of α- and β-ketophosphonates using chiral reactant derived from sodium borohydride and l-(+)- or d-(−)-tartaric acid is developed. The methodology was used for the preparation of a number of biologically interesting enantiomerically pure products: including 2,3-epoxypropylphosphonate 11, 2-hydroxy-3-aminopropylphosphonic acid 14 (phospho-GABOB), phospho-carnitine

  开发了一种高效且通用的方法，该方法使用衍生自硼氢化钠和1-（+）-或d-（-）-酒石酸的手性反应物不对称还原α-和β-酮膦酸酯。该方法被用于许多生物有趣对映体纯产品的制备：含2,3- epoxypropylphosphonate 11，2-羟基-3-氨基丙基膦酸14（磷酸- GABOB），磷酸-肉碱19，和其他在多克规模。
• Enantioselective reduction of ketophosphonates using chiral acid adducts with sodium borohydride
  作者：V. V. Nesterov、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363206070048

  日期：2006.7

  A method for asymmetric reduction of alpha- and beta-ketophosphonates using a chiral complex prepared from sodium borohydride and D- or L-tartaric acid is developed. Reduction of alpha- or beta-ketophosphonates by these reagents led to formation of corresponding (S)- or (R)-hydroxyphosphonates. Reduction of chiral di(1R,2S,5R)-menthylketophosphonates by the chiral complex NaBH4/(R,R)-tartaric acid due to the dual compliant asymmetric induction resulted in increased stereoselectivity of the reaction and led to formation of the hydroxyphosphonates with ee 90% or higher. On the other hand, reduction of di(1R,2S,5R)-methylketophosphonates by the chiral complex NaBH4/(S,S)-tartaric acid proceeded as non-compliant dual asymmetric induction and resulted in decreased reaction stereoselectivity leading to formation of hydroxyphosphonates with similar to 45-60% ee. The developed methodology was applied to the synthesis of (R)-phosphocarnifine in multigram amounts.
• New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine
  作者：Vitaly V. Nesterov、Oleg I. Kolodiazhnyi

  DOI：10.1016/j.tetasy.2006.03.025

  日期：2006.4

  The reduction of alpha- or beta-ketophosphonates with a chiral reactant 1, prepared from sodium borohydride and (R)- or (S)-tartaric acids, led to the formation of both (S)- and (R)-alpha- or beta-hydroxyphosphonates in high yields. The stereoselectivity of the reaction depended on the absolute configurations of 1 and the ketophosphonates. The reduction of di(1R,2S,5R)-menthyl ketophosphonates with (R)-1 proceeded with matched double asymmetric induction to give high diastereomeric excesses of hydroxyphosphonates (up to 96% de). This methodology was used for the preparation of enantiomerically pure phosphonate modified carnitine on a multigram scale. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of a phosphorus analog of natural l-carnitine
  作者：V. V. Nesterov、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363206090246

  日期：2006.9