dibenzyl 1-hydroxy-3-methylbutanephosphonate | 135087-12-6

• 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: dibenzyl 1-hydroxy-3-methylbutanephosphonate
• 英文别名: dibenzyl 1-hydroxy-3-methyl-butylphosphonate；1-bis(phenylmethoxy)phosphoryl-3-methylbutan-1-ol
• CAS: 135087-12-6
• 化学式: C₁₉H₂₅O₄P
• 分子量: 348.379
• InChiKey: KETIDANAICNRAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dibenzyl 1-hydroxy-3-methylbutanephosphonate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 以 四氯化碳 、 丙酮 、 苯 为溶剂， 反应 18.0h， 生成 2-tert-Butoxycarbonylamino-3-methyl-butyric acid 1-(bis-benzyloxy-phosphoryl)-3-methyl-butyl ester
  参考文献：
  名称：

  Hoffmann, M., Journal fuer Praktische Chemie (Leipzig), 1990, vol. 332, # 2, p. 251 - 255

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl hydrogen 1-hydroxy-3-methylbutanephosphonate 以 苯 为溶剂， 反应 4.0h， 生成 dibenzyl 1-hydroxy-3-methylbutanephosphonate
  参考文献：
  名称：

  Hoffmann, M., Journal fuer Praktische Chemie (Leipzig), 1990, vol. 332, # 2, p. 251 - 255

  摘要：

  DOI：

文献信息

• A Simple, Efficient Synthesis of Dibenzyl and Di-<i>p</i>-nitrobenzyl 1-Hydroxyalkanephosphonates
  作者：Maria Hoffmann

  DOI：10.1055/s-1988-33434

  日期：——

  Dibenzyl and di-p-nitrobenzyl 1-hydroxyalkanephosphonates 3a-i are prepared by alkylation of 1-hydroxyalkanephosphonic acids 1 with O-benzyl and O-(p-nitrobenzyl)-N,N′-dicyclohexylisoureas 2.

  二苯基和二对硝基苯基1-羟基烷基磷酸酯3a-i是通过将1-羟基烷基磷酸一酸1与O-苄基和O-(对硝基苯基)-N,N′-二环己基异脲2进行烷基化反应制备的。
• N-Hydroxy-α-amino phosphonate derivatives as potential haptens for eliciting catalytic antibodies
  作者：V. Gouverneur、M-N. Lalloz

  DOI：10.1016/0040-4039(96)01397-4

  日期：1996.8

  an efficient synthesis of N-hydroxy-α-amino phosphonate derivatives has been developed using a Mitsunobu reaction with N-phenoxycarbonyl-O-tert-butyl-alkoxycarbonyl hydroxylamine and α-hydroxy phosphonates.

  利用与N-苯氧基羰基-O-叔丁基-烷氧基羰基羟胺和α-羟基膦酸酯的Mitsunobu反应，已经开发出有效合成N-羟基-α-氨基膦酸酯衍生物的方法。
• Nafion®-supported oxovanadium-catalyzed hydrophosphonylation of aldehydes under solventless conditions
  作者：Shiue-Shien Weng、Guan-Ying Lin、Hsin-Chun Li、Kuo-Chen Yang、Teng-Mao Yang、Hui-Chi Liu、Syuan-Hua Sie

  DOI：10.1002/aoc.2879

  日期：2012.9

  A Nafion® resin‐supported oxovanadium(IV) catalyst was readily prepared via ion‐exchange method. This solid vanadyl perfluorinated sulfonate catalyst was used as an efficient and recoverable catalyst for the hydrophosphonylation of various aldehydes under solventless conditions at room temperature. The catalyst could be recovered by simple filtration and reused without a significant loss of activity

  可以通过离子交换方法轻松地制备Nafion®树脂负载的氧钒（IV）催化剂。将该固体钒基全氟化磺酸盐催化剂用作在室温下无溶剂条件下各种醛的氢膦酰化的有效且可回收的催化剂。可以通过简单的过滤来回收催化剂，并在不显着降低活性的情况下对其进行再利用。版权所有©2012 John Wiley＆Sons，Ltd.
• Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis
  作者：Pola Cybulska、Yves-Marie Legrand、Alicja Babst-Kostecka、Sébastien Diliberto、Anna Leśniewicz、Erwan Oliviero、Valérie Bert、Clotilde Boulanger、Claude Grison、Tomasz K. Olszewski

  DOI：10.3390/molecules27103075

  日期：——

  A green and effective approach for the synthesis of structurally diversed α-hydroxyphosphonates via hydrophosphonylation of aldehydes under solventless conditions and promoted by biosourced catalysts, called ecocatalysts “Eco-MgZnOx” is presented. Ecocatalysts were prepared from Zn-hyperaccumulating plant species Arabidopsis halleri, with simple and benign thermal treatment of leaves rich in Zn, and

  提出了一种绿色有效的方法，通过在无溶剂条件下醛的氢膦酰化和生物源催化剂的促进来合成结构多样的α-羟基膦酸酯，称为生态催化剂“Eco-MgZnOx”。生态催化剂是由锌超富集植物拟南芥（Arabidopsishalleri）制备而成，对富含锌的叶子进行简单而良性的热处理，无需任何进一步的化学处理。通过 MP-AES、XRPD、HRTEM 和 STEM-EDX 技术对 Eco-MgZnOx 的元素组成和结构进行了表征。这些分析揭示了两种不寻常且有价值的混合锌镁氧化物和铁镁氧化物的天然丰富性。本研究中使用生态催化剂来证明它们在醛的氢膦酰化中的潜在用途，从而产生各种α-羟基膦酸酯衍生物，这些衍生物是现代化学工业的关键组成部分。进行计算化学以帮助区分混合氧化物生态催化剂的一些成分的作用。该方案的主要优点是转化率高、底物范围广、反应条件温和、最终产物易于纯化以及生态催化剂的制备简单。此外，Eco-MgZnOx-P
• Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase
  作者：John Bird、Rachel C. De Mello、Gregory P. Harper、David J. Hunter、Eric H. Karran、Roger E. Markwell、Anette J. Miles-Williams、Shahzad S. Rahman、Robert W. Ward

  DOI：10.1021/jm00027a020

  日期：1994.1

  The synthesis of a series of N-phosphonoalkyl dipeptides 6 is described. Syntheses were devised that allowed the preparation of single diastereoisomers and the assignment of stereochemistry. The compounds were evaluated in vitro for their ability to inhibit the degradation of radiolabeled collagen by purified human lung fibroblast collagenase. Several of the compounds were potent collagenase inhibitors and were at least l0-fold more potent than their corresponding N-carboxyalkyl analogues. Activity was lost when the phosphonic acid group P(O)(OH)(2) was replaced by the phosphinic acid groups P(O)(H)(OH) and P(O)(Me)(OH). At the P-1 position, (R)- or (S)-allkyl groups, especially ethyl and methyl (e.g., 12a,b, 52a,b, and 53a,b), or an (R)-phenethyl moiety (55a) conferred high potency (IC50 values in the range 0.23-0.47 mu M). (S)-Stereochemistry was preferred for the P-1(') isobutyl side chain. Structure-activity relationships were also investigated at the P-2(') site, and interestingly, compounds with basic side chains such as the guanidine 57a, were equipotent with more lipophilic compounds, such as 52a. As with other series of collagenase inhibitors, potency was enhanced by introducing bicyclic aromatic P-2(') substituents. The most potent phosphonic acid of the series was the bicyclic aromatic P-2(') tryptophan analogue 59a (IC50 0.05 mu M).