diphenyl octylphosphonate | 21612-70-4

• 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: diphenyl octylphosphonate
• 英文别名: Octylphosphonsaeure-diphenylester；Diphenyl-octyl-phosphonat；[Octyl(phenoxy)phosphoryl]oxybenzene
• CAS: 21612-70-4
• 化学式: C₂₀H₂₇O₃P
• 分子量: 346.406
• InChiKey: CINZJKLTOKJRGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

合成制备方法

将2-乙基己醇、亚磷酸三苯酯和催化剂甲醇钠加入反应釜，在搅拌下升温至100～115℃进行酯交换反应。反应在负压下进行，脱出的苯酚回收后可再利用。产物静置过滤即为成品。

用途

本品在聚丙烯中与酚类抗氧剂并用，主要起抗氧、防脆变及消色作用。还可用作聚氯乙烯及其共聚物的辅助稳定剂。与金属盐或皂并用时，能显著改善聚氯乙烯的颜色，提高其耐光及耐候性，一般用量为0.5～2份。

此外，本品还可作为丁基橡胶的不污染性稳定剂、环氧树脂的稀释剂和改性剂。

反应信息

• 作为产物：
  描述：

  1-辛基二氯磷酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 diphenyl octylphosphonate
  参考文献：
  名称：

  Ethyl Octylphosphonofluoridate and Analogs: Optimized Inhibitors of Neuropathy Target Esterase

  摘要：

  The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The principal compounds studied are alkyl alkylphosphonofluoridates and dialkyl phosphorofluoridates. Potencies that exceed those of any previous inhibitors under the standard in vitro NTE assay condition are achieved with alkyl octylphosphonofluoridates (ethyl, isopropyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, and 3-iodopropyl), 2-iodoethyl hexylphosphonofluoridate, and dialkyl phosphorofluoridates [ethyl, nonyl; di(2-iodoethyl); di(3-iodopropyl); dipentyl]. The concentration for 50% NTE inhibition (I-50) Of these compounds is 0.04-0.14 nM. Thirty-eight less active analogs including aryl phosphonates and aryl phosphates give I(50)s of 0.27-4730 nM. For highest potency the summation of length of the alkyl and alkoxy groups on phosphorus should be 12-16 atoms (carbons, oxygens, and phosphorus) (a terminal iodo substituent in this relationship is equivalent to a propyl group). In general, the phosphonofluoridates and phosphorofluoridates are more active than analogs with leaving groups other than fluorine, i.e., phenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 3,4-dichlorophenoxy, and 4H-1,3,2-benzodioxaphosphorin. Considering the exceptional potencies of ethyl and 2-iodoethyl octylphosphonofluoridates (I50S of 0.04 and 0.09 nM, respectively), it is not surprising that at ip doses of 10-30 mg/kg they inhibit brain NTE by 82-97% 48 h after treatment. However, unexpectedly, only the ethyl but not the 2-iodoethyl compound induces OPIDN, possibly associated with the greater ease of aging for NTE inhibited with the ethyl than the 2-iodoethyl compound (as observed in vitro both spontaneously and on induction by potassium fluoride). The high potency of ethyl octylphosphonofluoridate and several analogs as NTE inhibitors suggests that they are useful probes in determining the toxicological features of this secondary lesion for organophosphorus poisoning.

  DOI：

  10.1021/tx00050a011

文献信息

• DBU-promoted alkylation of alkyl phosphinates and H-phosphonates
  作者：Laurent Gavara、Christelle Petit、Jean-Luc Montchamp

  DOI：10.1016/j.tetlet.2012.07.019

  日期：2012.9

  phosphinates and some H-phosphonate diesters is promoted by the base DBU. Only more reactive alkyl halides react in preparatively useful yields. However, the method provides easy access to important H-phosphinate building blocks, without the need for a protecting group strategy or metal catalysts. The reaction is conveniently conducted at, or below, room temperature. The preparation of methyl-H-phosphinate

  DBU碱促进烷基次膦酸酯和一些H-膦酸酯二酯的烷基化。只有更多的反应性烷基卤化物以制备有用的产率反应。但是，该方法无需重要的保护基策略或金属催化剂即可轻松获得重要的H-次膦酸酯结构单元。该反应方便地在室温或低于室温下进行。甲基的制备ħ -phosphinate酯是特别令人感兴趣的，因为它避免了以往更普遍使用methyldichlorophosphine MePCl的2。
• Feshchenko,N.G. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2468 - 2470
  作者：Feshchenko,N.G. et al.

  DOI：——

  日期：——
• THERMOPLASTIC ELECTROCHROMIC MATERIALS
  申请人：Percec Simona

  公开号：US20110147680A1

  公开（公告）日：2011-06-23

  Disclosed are electrochromic materials containing a film-forming polymer with a T g less than 100° C.; a plasticizer; an electrochromophore; an electron mediator; and a salt. Also disclosed are electrochromic devices using such electrochromic materials that can provide light-filtering, color-modulation, or reflectance-modulation in variable transmittance windows, variable-reflectance mirrors and other dynamic glazing applications.
• US8323534B2
  申请人：——

  公开号：US8323534B2

  公开（公告）日：2012-12-04
• Ethyl Octylphosphonofluoridate and Analogs: Optimized Inhibitors of Neuropathy Target Esterase
  作者：Shao-Yong Wu、John E. Casida

  DOI：10.1021/tx00050a011

  日期：1995.12

  The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The principal compounds studied are alkyl alkylphosphonofluoridates and dialkyl phosphorofluoridates. Potencies that exceed those of any previous inhibitors under the standard in vitro NTE assay condition are achieved with alkyl octylphosphonofluoridates (ethyl, isopropyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, and 3-iodopropyl), 2-iodoethyl hexylphosphonofluoridate, and dialkyl phosphorofluoridates [ethyl, nonyl; di(2-iodoethyl); di(3-iodopropyl); dipentyl]. The concentration for 50% NTE inhibition (I-50) Of these compounds is 0.04-0.14 nM. Thirty-eight less active analogs including aryl phosphonates and aryl phosphates give I(50)s of 0.27-4730 nM. For highest potency the summation of length of the alkyl and alkoxy groups on phosphorus should be 12-16 atoms (carbons, oxygens, and phosphorus) (a terminal iodo substituent in this relationship is equivalent to a propyl group). In general, the phosphonofluoridates and phosphorofluoridates are more active than analogs with leaving groups other than fluorine, i.e., phenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 3,4-dichlorophenoxy, and 4H-1,3,2-benzodioxaphosphorin. Considering the exceptional potencies of ethyl and 2-iodoethyl octylphosphonofluoridates (I50S of 0.04 and 0.09 nM, respectively), it is not surprising that at ip doses of 10-30 mg/kg they inhibit brain NTE by 82-97% 48 h after treatment. However, unexpectedly, only the ethyl but not the 2-iodoethyl compound induces OPIDN, possibly associated with the greater ease of aging for NTE inhibited with the ethyl than the 2-iodoethyl compound (as observed in vitro both spontaneously and on induction by potassium fluoride). The high potency of ethyl octylphosphonofluoridate and several analogs as NTE inhibitors suggests that they are useful probes in determining the toxicological features of this secondary lesion for organophosphorus poisoning.