diisopropyl aminomethylphosphonate | 86052-63-3

• 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: diisopropyl aminomethylphosphonate
• 英文别名: diisopropyl aminomethanephosphonate；Dipropan-2-yl (aminomethyl)phosphonate；di(propan-2-yloxy)phosphorylmethanamine
• CAS: 86052-63-3
• 化学式: C₇H₁₈NO₃P
• 分子量: 195.199
• InChiKey: YTAOPBOXQQWKJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• 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：

  diisopropyl aminomethylphosphonate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 diisopropyl phenethylphosphoramidate
  参考文献：
  名称：

  PO-Activated Olefination and Conversion of Aldehydes and Ketones to Higher Amines; II. Synthesis of Arylethylamines

  摘要：

  我们报道了通过三条不同路线将芳基羧醛和/或酮 2 转化为芳基乙胺 3 和/或 4。根据第一条路线，中间体亚胺膦酸盐 9 通过经典的 PO 活化烯化反应。第二条和第三条路线涉及亚胺膦酸盐 9 重排为乙烯基膦酸酰胺 12。

  DOI：

  10.1055/s-1987-27902
• 作为产物：
  描述：

  甲基磷酸二异丙酯 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 过氧化氢苯甲酰 、 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 60.0~140.0 ℃ 、101.33 kPa 条件下， 反应 49.0h， 生成 diisopropyl aminomethylphosphonate
  参考文献：
  名称：

  A Novel Synthesis of 1-Aminoalkylphosphonates

  摘要：

  A novel route has been devised for the preparation of a series of 1-aminoalkylphosphonate diesters, precursors to analogues of a-amino acids. The route involves a facile bromine substitution at the 1-position of alkylphosphonate diesters using N-bromosuccinimide, followed by azide ion displacement and catalytic hydrogenolysis.

  DOI：

  10.1080/00397919108019793

文献信息

• Enantioselective α-Aminophosphonate Functionalization of Indole Ring through an Organocatalyzed Friedel–Crafts Reaction
  作者：Aitor Maestro、Edorta Martinez de Marigorta、Francisco Palacios、Javier Vicario

  DOI：10.1021/acs.joc.8b02843

  日期：2019.1.18

  Chiral phosphoric acids efficiently catalyze the asymmetric Friedel–Crafts reaction of several indoles with α-iminophosphonates to afford enantioenriched hybrid α-aminophosphonate functionalized indole derivatives.

  手性磷酸可以有效地催化几个吲哚与α-亚氨基膦酸酯的不对称Friedel-Crafts反应，从而提供对映体富集的杂化α-氨基膦酸酯官能化的吲哚衍生物。
• Asymmetric Synthesis of α‐Amino Phosphonic Acids using Stable Imino Phosphonate as a Universal Precursor
  作者：Tsubasa Inokuma、Takuya Sakakibara、Takatoshi Someno、Kana Masui、Akira Shigenaga、Akira Otaka、Ken‐ichi Yamada

  DOI：10.1002/chem.201903572

  日期：2019.10.28

  A practical method for synthesizing chiral α-amino phosphonic acid derivatives was developed. Readily available and stable N-o-nitrophenylsulfenyl (Nps) imino phosphonate was utilized as a substrate for a highly enantioselective Friedel-Crafts-type addition of indole or pyrrole nucleophiles catalyzed by chiral phosphoric acid. The resulting adduct was easily converted into N-9-fluorenylmethyloxycarbonyl

  开发了一种合成手性α-氨基膦酸衍生物的实用方法。现成的稳定的No-nitrophenylsulfenyl（Nps）亚氨基膦酸酯用作手性磷酸催化的吲哚或吡咯亲核试剂的高对映选择性Friedel-Crafts型加成物的底物。所得的加合物易于转化为N-9-芴基甲氧基羰基（Fmoc）氨基膦酸，其可用于合成含有氨基膦酸的肽。
• Process for the preparation of .beta.-cyclo-substituted ethylamines
  申请人：Sanofi

  公开号：US04493931A1

  公开（公告）日：1985-01-15

  The present invention provides a multistep process for the preparation of .beta.-cyclo-substituted ethylamines of the general formula:- Ar--CH.sub.2 --CH.sub.2 --NH.sub.2 (I) in which AR is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly- substituted, wherein said compounds represent a class of intermediates which can be converted to 4,5,6,7-tetrahydro[3,2-C] or [2,3-C]pyridines wherein the latter are useful for anti-inflammatory, vasodilator or blood platelet aggregation inhibition activities.

  本发明提供了一种用于制备β-环代替乙胺的多步骤过程，其一般公式为：Ar--CH.sub.2 --CH.sub.2 --NH.sub.2（I），其中Ar是一种杂环或非杂环芳基，可以是单取代或多取代的，所述化合物代表一类中间体，可以转化为4,5,6,7-四氢[3,2-C]或[2,3-C]吡啶，后者可用于抗炎、扩血管或抑制血小板聚集活性。
• Haloacylaminoalkylphosphonates
  申请人：Ciba-Geigy Corporation

  公开号：US04579691A1

  公开（公告）日：1986-04-01

  When applied as safeners, the haloacylaminoalkylphosphinates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides of the formula I below are able to protect cultivated plants from the phytotoxic effects of herbicides. Suitable crops are preferably sorghum, cereals, rice, maize and soya beans and the herbicides employed are chloroacetanilides and thiocarbamates. The haloacylaminoalkylphosphonates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides have the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkoxy or C.sub.1 -C.sub.4 cyanoalkoxy, R.sub.2 is hydrogen or a substituent as defined for R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or one of R.sub.3 and R.sub.4 is also a radical ##STR2## or both taken together with the carbon atom to which they are attached are also a C.sub.3 -C.sub.11 cycloalkyl radical, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkoxy or aralkyl, R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl, X.sub.1 and X.sub.2 are each independently halogen or one of X.sub.1 and X.sub.2 is also hydrogen, and n is 1, 2 or 3.

  当作为安全剂应用时，以下公式I中的卤代酰氨基烷基膦酸酯、卤代酰氨基烷基膦酸酯和卤代酰氨基烷基膦氧化物能够保护栽培植物免受除草剂的植物毒性影响。适合的作物主要是高粱、谷物、稻米、玉米和大豆，所使用的除草剂是氯乙基苯胺和硫代氨基甲酸酯。卤代酰氨基烷基膦酸酯、卤代酰氨基烷基膦酸酯和卤代酰氨基烷基膦氧化物具有以下公式I##STR1##其中R.sub.1是C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4烷氧基、C.sub.2 -C.sub.4烯氧基、C.sub.2 -C.sub.4炔氧基、C.sub.1 -C.sub.4卤代烷基、C.sub.2 -C.sub.8烷氧基烷氧基或C.sub.1 -C.sub.4氰基烷氧基，R.sub.2是氢或类似R.sub.1定义的取代基，R.sub.3和R.sub.4分别独立地是氢、C.sub.1 -C.sub.4烷基或R.sub.3和R.sub.4中的一个也是基团##STR2##或者两者与它们连接的碳原子一起也是一个C.sub.3 -C.sub.11环烷基基团，R.sub.5是氢、C.sub.1 -C.sub.4烷基、C.sub.3 -C.sub.7环烷基、C.sub.2 -C.sub.4烯基、C.sub.2 -C.sub.4炔基、C.sub.2 -C.sub.8烷氧基烷基、C.sub.1 -C.sub.4卤代烷氧基或芳基烷基，R.sub.6是氢或C.sub.1 -C.sub.4烷基，X.sub.1和X.sub.2各自独立地是卤素或X.sub.1和X.sub.2中的一个也是氢，n为1、2或3。
• 5′-Phosphonate modified oligoadenylates as potent activators of human RNase L
  作者：Tomáš Lášek、Magdalena Petrová、Ivana Košiová、Ondřej Šimák、Miloš Buděšínský、Jaroslav Kozák、Jan Snášel、Zdeněk Vavřina、Gabriel Birkuš、Ivan Rosenberg、Ondřej Páv

  DOI：10.1016/j.bmc.2022.116632

  日期：2022.2

  major player in the interferon-induced antiviral defense mechanism of cells. Upon sensing viral dsRNA, 5′-phosphorylated 2′,5′-oligoadenylates are synthesized, and subsequently activate latent RNase L. To determine the influence of 5′-phosphate end on the activation of human RNase L, four sets of 5′-phosphonate modified oligoadenylates were prepared on solid-phase. The ability of these 5′-modified oligoadenylates

  寡腺苷酸合成酶-核糖核酸酶 L 途径是干扰素诱导的细胞抗病毒防御机制的主要参与者。在感知病毒 dsRNA 后，合成 5'-磷酸化的 2',5'-寡腺苷酸，随后激活潜伏的 RNase L。为了确定 5'-磷酸末端对人 RNase L 激活的影响，四组 5'-在固相上制备膦酸酯修饰的寡腺苷酸。探索了这些带有缩短的、等排的和延长的膦酸酯键的 5'-修饰的寡腺苷酸激活 RNase L 的能力。我们发现等排键和延长一个原子的键通常被具有 EC 50的酶很好地耐受值与天然活化剂相当。相反，缩短一个原子或延长两个原子的键的活性降低。