2-(diisopropoxyphosphoryl) acetic acid | 118729-24-1

• 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: 2-(diisopropoxyphosphoryl) acetic acid
• 英文别名: Acetic acid, diisopropylphosphono-；2-di(propan-2-yloxy)phosphorylacetic acid
• CAS: 118729-24-1
• 化学式: C₈H₁₇O₅P
• 分子量: 224.194
• InChiKey: NWYWXXQNZRWXDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  329.4±25.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(diisopropoxyphosphoryl) acetic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Diisopropoxyphosphinyl)acetylchlorid
  参考文献：
  名称：

  WO2020033784A5

  摘要：

  公开号：

  WO2020033784A5
• 作为产物：
  描述：

  三异丙基亚磷酸酯 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 2-(diisopropoxyphosphoryl) acetic acid
  参考文献：
  名称：

  WO2020033784A5

  摘要：

  公开号：

  WO2020033784A5

文献信息

• Synthesis and hybridization of oligonucleotides modified at AMP sites with adenine pyrrolidine phosphonate nucleotides
  作者：Dominik Rejman、Petr Kočalka、Radek Pohl、Zdeněk Točík、Ivan Rosenberg

  DOI：10.1135/cccc2009022

  日期：——

  Three structurally diverse types of the protected pyrrolidine nucleoside phosphonates were prepared as the monomers for the introduction of pyrrolidine nucleotide units into modified oligonucleotides on the solid phase. Two different chemistries were used for incorporation of modified and natural units: the phosphotriester method for the former, i.e., monomers containing N-phosphonoalkyl and N-phosphonoacyl moieties attached to the pyrrolidine ring nitrogen atom, and phosphoramidite chemistry for the latter. Since the synthesized pyrrolidine nucleoside phosphonic acids are close mimics of the 3′-deoxynucleoside 5′-phosphates, the incorporation of one modified unit into oligonucleotides gives rise to one 2′,5′ internucleotide linkage. A series of nonamers containing two or three modified units, as well as the fully modified adenine 15-mer, were synthesized in reverse order, i.e., from the 5′ to the 3′ end of the strand. The measurement of thermal characteristics of the complexes of modified nonamers with the complementary strand revealed a destabilizing effect of the introduced modification. The modified adenine homooligonucleotide, was found to form the most stable complex with oligothymidylate of all the tested modified oligonucleotides in terms of ΔT_m per modification.

  三种结构多样的保护吡咯烷基核苷酸膦酸酯被制备为单体，用于在固相上引入吡咯烷核苷酸单元到修饰寡核苷酸中。采用两种不同的化学方法来合成修饰和天然单元：前者采用磷酸三酯法，即含有连接到吡咯烷环氮原子的N-膦酸烷基和N-膦酸酰基的单体，后者采用磷酸酰胺化学方法。由于合成的吡咯烷基核苷酸膦酸是3'-去氧核苷酸5'-膦酸的近似物，因此将一个修饰单元引入到寡核苷酸中会产生一个2',5'间核苷酸连接。一系列包含两个或三个修饰单元的九聚体以及完全修饰的腺嘌呤15聚体是以相反的顺序合成的，即从链的5'端到3'端。测量修饰九聚体与互补链形成的复合物的热特性表明，引入修饰会导致复合物不稳定。在所有测试的修饰寡核苷酸中，修饰腺嘌呤同源寡核苷酸与寡胸苷酸形成的复合物具有最稳定的ΔTm值。
• 一种高选择性制备马来酸阿法替尼的方法
  申请人：南京臣功制药股份有限公司

  公开号：CN106243092B

  公开（公告）日：2019-02-15

  本发明涉及一种高选择性制备马来酸阿法替尼的方法，包括如下步骤：(1)以N4‑(3‑氯‑4‑氟苯基)‑7‑[[(3S)‑四氢‑3‑呋喃基]氧基]‑4,6‑喹唑啉二胺为起始原料，与二异丙基磷乙酸进行缩合反应；(2)步骤1的产物与2‑二甲基氨基‑1‑羟基磺酸钠发生Horner‑Wadsworth‑Emmons反应；(3)步骤2的产物与马来酸反应成盐得到马来酸阿法替尼。本发明的产品顺式异构体极少，单杂全部控制在0.1％以下，品质优良，适宜用于大量制备成品，符合ICH规定的药用原料药的要求。
• Column Chromatography-Free Solution-Phase Synthesis of a Natural Piper-Amide-like Compound Library
  作者：Sumin Kim、Chaemin Lim、Sukjin Lee、Seokwoo Lee、Hyunkyung Cho、Joo-Youn Lee、Dong Sup Shim、Hee Dong Park、Sanghee Kim

  DOI：10.1021/co400003d

  日期：2013.4.8

  We have achieved an efficient solution-phase parallel synthesis of a library of natural piper-amide-like compounds from the bifunctional beta-phosphono-N-hydroxy-succinimidyl ester intermediate. The primary important feature in our study is the construction of natural-product-like molecules through the adaptation of sophisticated organic reactions that create water-soluble byproducts for a chromatography-free purification. This simple and efficient method rapidly provides a combinatorial library of high yield and purity. The library was evaluated against GPCR targets to demonstrate its potential use as a tool for drug discovery and in chemical biology.
• Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase
  作者：Petr Kočalka、Dominik Rejman、Václav Vaněk、Markéta Rinnová、Ivana Tomečková、Šárka Králíková、Magdalena Petrová、Ondřej Páv、Radek Pohl、Miloš Buděšínský、Radek Liboska、Zdeněk Točík、Natalya Panova、Ivan Votruba、Ivan Rosenberg

  DOI：10.1016/j.bmcl.2009.12.081

  日期：2010.2

  Structurally diverse, sugar-modified, thymine-containing nucleoside phosphonic acids were evaluated for their ability to inhibit thymidine phosphorylase (TP, EC 2.4.2.4) purified from spontaneous T-cell lymphomas of an inbred Sprague-Dawley rat strain. From a large set of tested compounds, among them a number of pyrrolidine-based derivatives, 10 nucleotide analogues with IC50 values below 1 mu M were selected. Out of them, four compounds strongly inhibited the enzyme with IC50 values lying in a range of 11-45 nM. These most potent compounds might be bi-substrate analogues. (C) 2009 Elsevier Ltd. All rights reserved.
• Total synthesis of rhizoxin D
  作者：David R. Williams、Kim M. Werner、Bainian Feng

  DOI：10.1016/s0040-4039(97)01605-5

  日期：1997.9

  The convergent, enantiocontrolled synthesis of a significant antimitotic agent for cancer chemotherapy is presented with completion of rhizoxin diene 2. (C) 1997 Elsevier Science Ltd.

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