diethyl 1-aminocyclohexylphosphonate | 56372-35-1

• 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 1-aminocyclohexylphosphonate
• 英文别名: (1-amino-cyclohexyl)-phosphonic acid diethyl ester；(1-Amino-cyclohexyl)-phosphonsaeure-diaethylester；1-Aminocyclohexanphosphonsaeure-diethylester；Phosphonic acid, (1-aminocyclohexyl)-, diethyl ester；1-diethoxyphosphorylcyclohexan-1-amine
• CAS: 56372-35-1
• 化学式: C₁₀H₂₂NO₃P
• 分子量: 235.263
• InChiKey: IZRMCJYZYOYIJR-UHFFFAOYSA-N

物化性质

• 沸点：
  114-116 °C(Press: 1 Torr)
• 密度：
  1.0695 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-aminocyclohexylphosphonate 生成 [1-(2-Phosphono-acetylamino)-cyclohexyl]-phosphonic acid
  参考文献：
  名称：

  Plant-growth-regulatingN-(phosphonoacetyl)amines

  摘要：

  AbstractA series of N‐(phosphonacetyl)amine derivatives were synthesized and screened for plant‐growth regulating activity on Lepidium sativum L. and Cucumis sativus L. Aromatic N‐(phosphonoacetyl)amines. which may be considered as possible analogues of N‐acylaniline herbicides obtained by replacement of their acyl group by the phosphonacetyl moiety, exhibited significant or moderate herbicidal activity. In contrast, N‐(phosphonoacetyl)amino acids and N‐(phosphonoacetyl)aminophosphonic acids promoted the growth of L. sativum and C. sativus roots.

  DOI：

  10.1002/ps.2780400110
• 作为产物：
  描述：

  Cyclohexyl-phosphonic acid diethyl ester 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， -78.0~25.0 ℃ 、100.0 kPa 条件下， 反应 7.5h， 生成 diethyl 1-aminocyclohexylphosphonate
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic AcidsviaElectrophilic Azidation of Cycloalkylphosphonates

  摘要：

  alpha-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, hydrogenation of the intermediate alpha-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting alpha-amino cycloalkyl-phosphonates (12).

  DOI：

  10.1080/00397919608004650

文献信息

• A Novel Catalytic Three-Component Synthesis (Kabachnick-Fields Reaction) of α-Aminophosphonates from Ketones
  作者：Elena D. Matveeva、Nikolay S. Zefirov、Tatyana A. Podrugina、Elena V. Tishkovskaya、Larisa G. Tomilova

  DOI：10.1055/s-2003-42118

  日期：——

  A novel and highly convenient catalytic variant of the synthesis of α-aminophosphonates on basis of the Kabachnik-Fields reaction [three-component reaction of ketones, diethylphosphite and either benzylamine (series a) ofammonium carbonate (series b)] in the presence of tetra-tert-butylphthalocyanines has been developed. This method affords α-aminophosphonates in acceptable yields for various ketones

  基于 Kabachnik-Fields 反应 [酮、亚磷酸二乙酯和碳酸铵（系列 b）的苄胺（系列 b）的三组分反应]合成 α-氨基膦酸酯的一种新型且非常方便的催化变体-叔丁基酞菁已被开发。该方法以可接受的产率为各种酮提供 α-氨基膦酸酯，包括环状酮、空间位阻酮和笼酮。未取代的α-氨基膦酸也从b系列的相应酯中获得。
• One-pot synthesis of primary 1-aminophosphonates: Coupling reaction of carbonyl compounds, hexamethyldisilazane, and diethyl phosphite catalyzed by Al(OTf)₃
  作者：Sara Sobhani、Zahra Tashrifi

  DOI：10.1002/hc.20517

  日期：——

  Al(OTf)3 has been utilized as a new and efficient catalyst for the selective synthesis of primary 1-aminophosphonates by a one-pot coupling reaction of various types of aldehydes/ketones, hexamethyldisilazane, and diethyl phosphite under solvent-free conditions. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:109–115, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI

  Al(OTf)3 已被用作一种新型高效催化剂，通过各种醛/酮、六甲基二硅氮烷和亚磷酸二乙酯在无溶剂条件下的一锅偶联反应选择性合成伯 1-氨基膦酸酯。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:109–115, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20517
• Molecular amino-phosphonate cobalt–lanthanide clusters
  作者：Eufemio Moreno Pineda、Floriana Tuna、Robin G. Pritchard、Andrew C. Regan、Richard E. P. Winpenny、Eric J. L. McInnes

  DOI：10.1039/c3cc40907d

  日期：——

  The use of 1-amino-1-cyclohexyl phosphonic acid, a functionalised phosphonate, leads to the synthesis of two new structural types for 3d–4f phosphonate cages with unusual structural cores and which show high magnetocaloric effects.

  通过使用 1-amino-1-cyclohexyl phosphonic acid（一种功能化膦酸盐），我们合成了两种新结构类型的 3dâ4f膦酸盐笼，它们具有不同寻常的结构核心，并显示出很高的磁ocaloric效应。
• An Efficient One-Pot Synthesis of 1-Aminophosphonates
  作者：Babak Kaboudin、Samaneh Faghih、Sajedeh Alavi、Mohammad Reza Naimi-Jamal、Alireza Fattahi

  DOI：10.1055/a-1941-1242

  日期：2023.1

  The three-component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1-aminophosphonates in good to excellent yields under solvent- and catalyst-free conditions at ambient temperature. Hydrophosphorylation of imines in the presence of dialkyl phosphite under the same conditions gave also 1-aminophosphonates in good to excellent yields. These results showed that the

  1-氨基膦酸盐是有价值的化合物，在生物和工业中具有广泛的应用。已经报道了通过三组分（亚磷酸二烷基酯 + 醛 + 胺）或双组分反应（亚磷酸二烷基酯 + 亚胺）合成 1-氨基膦酸酯的各种反应条件和催化剂。这里报道了在非常温和的反应条件下无溶剂合成 1-氨基膦酸盐。在环境温度和无溶剂和无催化剂条件下，亚磷酸二烷基酯、羰基化合物和胺的三组分缩合反应以良好至优异的产率得到 1-氨基膦酸酯。在相同条件下在亚磷酸二烷基酯存在下亚胺的氢磷酸化也以良好至极好的产率得到1-氨基膦酸酯。这些结果表明该反应不需要催化剂或溶剂来活化。似乎亚磷酸二烷基酯（作为组分之一）的互变异构形式催化了该反应。使用任何溶剂都会降低反应产率。此外，还报道了一种新的合成方法在 TCCA 存在下，N-PMP 1-氨基膦酸盐的N-去保护 1-氨基膦酸盐（1-氨基酸的类似物） 。为了了解无溶剂条件下亚磷酸二烷基酯的活性，DFT 计算提供了对该活性基础的深入了解。
• Al(OTf)₃as an Efficient Catalyst for One-Pot Synthesis of Primary Diethyl 1-Aminophosphonates Under Solvent-Free Conditions
  作者：Sara Sobhani、Zahra Tashrifi

  DOI：10.1080/00397910802369695

  日期：2008.12.16

  A simple and general method has been developed for the one-pot, three-component synthesis of a variety of primary 1-aminophosphonates catalyzed by Al(OTf)(3) under solvent-free conditions in good to high yields.