1-(4-chlorophenyl)-1-hydroxymethylphosphonic acid | 63694-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-1-hydroxymethylphosphonic acid
• 英文别名: (4-Chlorophenyl)(hydroxy)methylphosphonic acid；[(4-chlorophenyl)-hydroxymethyl]phosphonic acid
• CAS: 63694-16-6
• 化学式: C₇H₈ClO₄P
• 分子量: 222.565
• InChiKey: HPPXSNUAVNMIES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (alpha-羟基-4-氯苄基)膦酸二乙酯 在 盐酸 、 水 作用下， 生成 1-(4-chlorophenyl)-1-hydroxymethylphosphonic acid
  参考文献：
  名称：

  新型二烷氧基磷酰基芳基甲基2-(4,6-二甲氧基嘧啶-2-基氧基)苯甲酸酯衍生物的合成及除草活性

  摘要：

  摘要 设计并合成了一系列二烷氧基磷酰基芳基甲基2-(4,6-二甲氧基嘧啶-2-基氧基)苯甲酸酯衍生物。所有新化合物均通过元素分析、红外 (IR)、1H-NMR 和质谱 (MS) 鉴定。检测了它们对一组杂草的除草活性。一些化合物显示出潜在的除草活性，这为进一步研究结构修饰提供了一些指示。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要

  DOI：

  10.1080/10426507.2010.511512

文献信息

• Synthesis and Herbicidal Activity of Novel Dialkoxyphosphoryl Aryl Methyl 2-(4,6-Dimethoxypyrimidin-2-yloxy) Benzoate Derivatives
  作者：Chuanfei Jin、Hongwu He

  DOI：10.1080/10426507.2010.511512

  日期：2011.7.1

  series of dialkoxyphosphoryl aryl methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy) benzoate derivatives was designed and synthesized. All new compounds were identified by elemental analysis, infrared (IR), 1H-NMR, and mass spectrometry (MS). Their herbicidal activity against a set of weed species was examined. Some of the compounds showed potential herbicidal activity, which provided some indications for further

  摘要 设计并合成了一系列二烷氧基磷酰基芳基甲基2-(4,6-二甲氧基嘧啶-2-基氧基)苯甲酸酯衍生物。所有新化合物均通过元素分析、红外 (IR)、1H-NMR 和质谱 (MS) 鉴定。检测了它们对一组杂草的除草活性。一些化合物显示出潜在的除草活性，这为进一步研究结构修饰提供了一些指示。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• SILYL PHOSPHITES V. THE REACTIONS OF TRIS(TRIMETHYLSILYL) PHOSPHITE WITH CARBONYL COMPOUNDS
  作者：Mitsuo Sekine、Isamu Yamamoto、Akio Hashizume、Tsujiaki Hata

  DOI：10.1246/cl.1977.485

  日期：1977.5.5

  When tris(trimethylsilyl) phosphite (1) was treated with aldehydes, ketones, or α,β-unsaturated aldehydes at room temperature, the 1,2-adducts were obtained in high yields (75–94%). On the other hand, when α,β-unsaturated ketones or ethyl crotonate was used, the 1,4-adducts were obtained in high yields (71–84%). The silylated products were smoothly hydrolyzed to the corresponding phosphonates in almost

  当亚磷酸三（三甲基甲硅烷基）酯 (1) 在室温下用醛、酮或 α,β-不饱和醛处理时，1,2- 加合物以高产率 (75-94%) 获得。另一方面，当使用 α,β-不饱和酮或巴豆酸乙酯时，1,4-加合物的产率很高（71-84%）。通过添加醇或水，硅烷化产物以几乎定量的产率顺利水解为相应的膦酸酯。
• Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
  作者：Zita Rádai、Tímea Windt、Veronika Nagy、András Füredi、Nóra Zsuzsa Kiss、Ivan Ranđelović、József Tóvári、György Keglevich、Gergely Szakács、Szilárd Tóth

  DOI：10.1039/c9nj02144b

  日期：——

  active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure–activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line

  我们合成了取代的苯甲醛衍生的α-羟基膦酸酯（αOHP），α-羟基膦酸（αOHPA）和α-膦酰氧基膦酸酯（αOPP），并表征了它们对一组癌细胞系的细胞毒性。使用基于荧光的细胞毒性试验，针对Mes-Sa亲本和Mes-Sa / Dx5多药耐药子宫肉瘤细胞系筛选了包含56个类似物的文库。细胞毒性筛选显示，二苄基-αOHP和二甲基-α-二苯基-OPP是最活跃的簇，这鼓励我们合成进一步的二苄基-α-二苯基-OPP衍生物，引起明显的细胞杀伤作用。进一步的结构-活性关系显示疏水性和主苯环上取代基的位置与毒性有关。事实证明，最活跃的类似物是同等的，
• Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
  作者：Nikoletta Harsági、Zita Rádai、Áron Szigetvári、János Kóti、György Keglevich

  DOI：10.3390/molecules25173793

  日期：——

  acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The

  监测 α-羟基苄基膦酸酯和一些相关衍生物的两步酸性水解，以确定动力学并绘制不同取代的膦酸酯在水解中的反应性。吸电子取代基增加了速率，而放电子取代基减慢了反应速度。两个水解步骤都以伪一级速率常数为特征。发现第二个 POC 键的裂变是决定速率的步骤。
• Tailoring the Structure of Aminobisphosphonates To Target Plant P5C Reductase
  作者：Giuseppe Forlani、Andrea Occhipinti、Łukasz Berlicki、Gabriela Dziedzioła、Anna Wieczorek、Paweł Kafarski

  DOI：10.1021/jf800029t

  日期：2008.5.1

  Using the structure of (3,5-dichlorophenyl)aminomethylenebisphosphonic acid as a lead compound, 25 new phosphonates were synthesized and evaluated as possible inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate (P5C) reductase. Derivatives substituted in the phenyl ring retained the inhibitory potential, though to a different extent. On the contrary any variation in the scaffold, i.e., the replacement of the second phosphonate moiety with a hydroxyl or an amino residue, resulted in a significant loss of biological activity. The availability of several structures capable of interfering with the catalytic mechanism in the micromolar to millimolar range allowed a proper structure-activity relationship analysis, leading us to hypothesize about the steric and electronic requirements for maintenance or enhancement of the inhibitory properties. Reversal experiments with suspension cultured cells provided evidence for the occurrence of enzyme inhibition in vivo. Because in higher plants the step catalyzed by P5C reductase is shared by all pathways leading to proline synthesis, these compounds may be exploited for the design of new substances endowed with herbicidal activity.