di-(1R,2S,5R)-menthyl α-hydroxybenzylphosphonate | 889103-63-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: di-(1R,2S,5R)-menthyl α-hydroxybenzylphosphonate
• 英文别名: di(1R,2S,5R)-menthyl hydroxy(phenyl)methylphosphonate；di(-)-menthyl [hydroxy(phenyl)methyl]phosphonate；bis[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy]phosphoryl-phenylmethanol
• CAS: 889103-63-3
• 化学式: C₂₇H₄₅O₄P
• 分子量: 464.626
• InChiKey: DQRWNVQUCUAZIB-IVBYXUCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.83
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  di-(1R,2S,5R)-menthyl α-hydroxybenzylphosphonate 在 sodium tetrahydroborate 、 重铬酸吡啶 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 di(1R,2S,5R)-menthyl (S)-hydroxy(phenyl)methylphosphonate
  参考文献：
  名称：

  不对称还原α-和β-酮膦酸酯的有效方法

  摘要：

  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。

  DOI：

  10.1016/j.tet.2007.04.101
• 作为产物：
  描述：

  di-(1R,2S,5R)-menthyl benzoylphosphonate 在 (S,S)-Na[BH₂(tartrate)] 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 di-(1R,2S,5R)-menthyl α-hydroxybenzylphosphonate
  参考文献：
  名称：

  Enantioselective reduction of ketophosphonates using chiral acid adducts with sodium borohydride

  摘要：

  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.

  DOI：

  10.1134/s1070363206070048

文献信息

• Catalytic synthesis of α-hydroxyphosphonates
  作者：M. M. Kabachnik、L. I. Minaeva、I. P. Beletskaya

  DOI：10.1134/s1070428009080016

  日期：2009.8

  Reactions of carbonyl compounds of aliphatic, aromatic, and heteroaromatic series with dialkyl phosphites in the presence of DBN were studied under microwave irradiation.
• Enantioselective Synthesis of α-Hydroxyalkylphosphonates
  作者：V. V. Nesterov、O. I. Kolodyazhnyi

  DOI：10.1007/s11176-005-0386-8

  日期：2005.7