(S)-pyrrolidine-2-phosphonic acid | 98049-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-pyrrolidine-2-phosphonic acid
• 英文别名: (S)-Pyrrolidin-2-ylphosphonic acid；[(2S)-pyrrolidin-2-yl]phosphonic acid
• CAS: 98049-01-5
• 化学式: C₄H₁₀NO₃P
• 分子量: 151.102
• InChiKey: BTURSMUPRYMLJE-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-Diethoxyphosphorylpyrollidine 在 盐酸 、 methyloxirane 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 (S)-pyrrolidine-2-phosphonic acid
  参考文献：
  名称：

  在直接不对称醛醇缩合反应中，氨基膦酸酯作为有机催化剂：在路易斯碱存在下，对顺式选择性。

  摘要：

  已经合成了手性α-氨基膦酸酯，并在直接不对称醛醇缩合反应中将其性能作为有机催化剂进行了评估。对于一系列取代的环己酮和苯甲醛，实现了高对映选择性（高达99％ee）。几种有机碱，例如DBU，DBN和TMG，与Aldol反应中的α-氨基膦酸酯一起使用，发现它们有利于顺式选择性。

  DOI：

  10.1039/b605091c

文献信息

• Synthesis of novel (R)- and (S)-piperidazine-3-phosphonic acids and transformation into (R)- and (S)-pyrrolidine-2-phosphonic acids
  作者：Mamoru Kaname、Yasushi Arakawa、Shigeyuki Yoshifuji

  DOI：10.1016/s0040-4039(01)00283-0

  日期：2001.4

  The first synthesis of a pair of (R)- and (S)-piperidazine-3-phosphonic acids was performed via a one-pot process of hetero Diels–Alder reaction and Lewis acid-catalyzed phosphonylation. The absolute configuration of the target compounds was established by a novel transformation into known (R)- and (S)-pyrrolidine-2-phosphonic acids.

  一对（R）-和（S）-哌啶嗪-3-膦酸的首次合成是通过杂Diels-Alder反应和路易斯酸催化的膦酰化反应的一锅法完成的。通过新颖转化为已知的（R）-和（S）-吡咯烷-2-膦酸来确定目标化合物的绝对构型。
• A novel and simple method for the preparation of (R)- and (S)-pyrrolidine-2-phosphonic acids: phosphonic acid analogues of proline
  作者：Babak Kaboudin、Jun-ya Kato、Hiroshi Aoyama、Tsutomu Yokomatsu

  DOI：10.1016/j.tetasy.2013.10.013

  日期：2013.12

  A simple and convenient method has been developed for the preparation of (R)- and (S)-pyrrolidine-2-phosphonic acids. The thermal reaction of proline with diethyl phosphite in the presence of benzaldehyde gave an N-benzyl derivative of diethyl pyrrolidine-2-phosphonate, which was transformed into two diastereomeric amides by sequential debenzylation and acylation with (+)-dibenzoyl-l-tartaric anhydride

  已经开发了一种简单方便的方法来制备（R）-和（S）-吡咯烷-2-膦酸。在苯甲醛存在下脯氨酸与亚磷酸二乙酯的热反应得到吡咯烷-2-膦酸二乙酯的N-苄基衍生物，通过依次脱苄基作用并用（+）-二苯甲酰基-1-酒石酸酐酰化将其转化为两种非对映体酰胺。通过柱色谱分离两种非对映异构酰胺，并通过X射线晶体学分析确定它们之一的结构。以常规方式水解酰胺得到（R）-和（S）-吡咯烷-2-膦酸。本方法的优点是容易，快速并且制备了吡咯烷-2-膦酸的两种对映体。
• Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers
  作者：Alicia Arizpe、María Rodríguez-Mata、Francisco J. Sayago、María J. Pueyo、Vicente Gotor、Ana I. Jiménez、Vicente Gotor-Fernández、Carlos Cativiela

  DOI：10.1016/j.tetasy.2015.10.016

  日期：2015.12

  The preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, Pro(P)) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate. (c) 2015 Elsevier Ltd. All rights reserved.