diethyl (morpholinomethyl)phosphonate | 27353-29-3

• 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: diethyl (morpholinomethyl)phosphonate
• 英文别名: diethyl morpholinomethylphosphonate；morpholin-4-ylmethyl-phosphonic acid diethyl ester；morpholinomethyl-phosphonic acid diethyl ester；Morpholinomethyl-phosphonsaeure-diaethylester；4-(Diethoxyphosphorylmethyl)morpholine
• CAS: 27353-29-3
• 化学式: C₉H₂₀NO₄P
• 分子量: 237.236
• InChiKey: QDSFNOHWQKVVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (morpholinomethyl)phosphonate 在 Hg(II)-EDTA 作用下， 以 水 为溶剂， 反应 1.0h， 以7%的产率得到3-Oxomorpholino-methan-phosphonsaeure-diethylester
  参考文献：
  名称：

  Moehrle, Hans; Vetter, Wolfgang, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1988, vol. 43, # 12, p. 1662 - 1671

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉-4-基苯甲酸酯 、 甲基膦酸二乙酯 在 Zn(TMP)₂ 、 2,2'-联吡啶 、 copper dichloride 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到diethyl (morpholinomethyl)phosphonate
  参考文献：
  名称：

  铜催化的膦酸酯和氧化膦的α-胺化：α-氨基膦酸及其衍生物的直接方法

  摘要：

  通过使用α-膦酸锌与O-酰基羟胺的铜催化亲电胺化反应，已经开发出一种直接处理重要的α-氨基膦酸及其衍生物的方法。该胺化作用提供了CN键形成的第一个示例，该步骤可以一步一步将无环和环状胺直接引入膦酸酯的α-位。在低至0.5摩尔％的催化剂下，该反应易于在室温下促进，并在广泛的底物范围内显示出高效率。

  DOI：

  10.1002/anie.201308890

文献信息

• Catalyst-Free and Selective C–N Bond Functionalization: Stereospecific Three-Component Coupling of Amines, Dichloromethane, and >P(O)H Species Affording α-Aminophosphorus Compounds
  作者：Yalei Zhao、Xiuling Chen、Tieqiao Chen、Yongbo Zhou、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1021/jo501961h

  日期：2015.1.2

  and selective C–N bond functionalization has been achieved through three-component coupling of amines, dihalomethane, and >P(O)H species. This reaction takes place stereospecifically with retention of configuration at phosphorus, which can produce various new optically active phosphorus analogues of α-amino acids.

  通过胺，二卤甲烷和> P（O）H物质的三组分偶联，实现了无催化剂和选择性C–N键的官能化。该反应立体定向地进行，并且保留了在磷处的构型，这可以产生各种新的α-氨基酸的旋光性磷类似物。
• Design and synthesis of macrocyclic ligands for specific interaction with crystalline ettringite and demonstration of a viable mechanism for the setting of cement
  作者：Jonathan L. W. Griffin、Peter V. Coveney、Andrew Whiting、Roger Davey

  DOI：10.1039/a902760b

  日期：——

  Cementitious materials are among those most widely used by mankind while being among the least well understood. The detailed physicochemical processes involved in the hydration and setting of cement slurries are very complex, and a clearly defined quantitative account is still lacking; indeed, even the composition of the cement powder itself is not known exactly. Still less has there been any understanding of the mechanism by which numerous known retarders of the cement setting process act. In this article, we detail the synthesis of novel macrocyclic organophosphonate retarders 1a and 2a which were developed by rational methods. Attempts to synthesise these compounds as phosphonate ester derivatives were universally unsuccessful, however direct modification of the parent hexaaza- (3) and trioxatriaza-18-crown-6 (5) derivatives was successful, to provide the phosphonic acids 1b and 2b respectively. Subsequent testing of these compounds showed their ability to inhibit the growth of crystalline ettringite and delay the setting of cement. These results support the hypothesis that the formation of crystalline ettringite is the rate determining step in the setting of cement.

  水硬性材料是人类使用最广泛却最不为人所了解的材料之一。水泥浆体的水化和凝结涉及的详细的物理化学过程非常复杂，目前仍缺乏明确的定量解释；事实上，甚至连水泥粉体的成分也无法确切知晓。更不用说，对于已知的大量抑制水泥凝结过程的缓凝剂的作用机理也缺乏了解。在本文中，我们详细介绍了新型大环有机膦酸酯缓凝剂1a和2a的合成过程，这些缓凝剂是通过合理方法开发的。然而，尝试将这些化合物合成磷酸酯衍生物均未成功，相反，直接修饰母体六氮杂（3）和三氧三氮杂-18-冠-6（5）衍生物获得了成功，分别得到了膦酸1b和2b。随后对这些化合物的测试表明，它们能够抑制结晶钙矾石的生长并延缓水泥的凝结。这些结果支持了如下假设：结晶钙矾石的形成是水泥凝结速率的决定步骤。
• Efficient Synthesis of Phosphono‐ and Phosphinoxidomethylated N‐Heterocycles under Solvent‐Free Microwave Conditions
  作者：Ibolya Prauda、István Greiner、Krisztina Ludányi、György Keglevich

  DOI：10.1080/00397910601033856

  日期：2007.2.1

  Abstract Simple N‐heterocycles were converted to N‐phosphono‐ and phosphinoxidomethyl derivatives by a solvent‐free microwave‐assisted condensation of the heterocycle, paraformaldehyde, and diethylphosphite or diphenylphosphine oxide in a convenient and, in most cases, efficient way. In contrast to an earlier report, imidazole proved to be unreactive in this type of phospha‐Mannich reaction.

  摘要 通过杂环、多聚甲醛和二乙基亚磷酸酯或二苯基氧化膦的无溶剂微波辅助缩合，以一种方便且在大多数情况下有效的方式将简单的 N-杂环转化为 N-膦酰基和膦氧化甲基衍生物。与之前的报道相反，咪唑被证明在这种类型的磷-曼尼希反应中没有反应。
• Quaternary aminomethyl phosphonates as scale inhibitors
  申请人：Petrolite Corporation

  公开号：US04420399A1

  公开（公告）日：1983-12-13

  This invention relates to quaternary aminomethyl phosphonates and uses thereof for example as scale inhibitors, corrosion inhibitors, chelating agents, etc.

  本发明涉及四元氨甲基膦酸盐及其用途，例如作为阻垢剂、缓蚀剂、螯合剂等。
• Savignac,P.; Lavielle,G., Bulletin de la Societe Chimique de France, 1974, p. 1506 - 1508
  作者：Savignac,P.、Lavielle,G.

  DOI：——

  日期：——

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