二正戊基磷酸酯 | 14254-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: 二正戊基磷酸酯
• 英文名称: di-n-pentyl phosphorchloridate
• 英文别名: dipentyl chlorophosphate；Phosphorochloridic acid, dipentyl ester；1-[chloro(pentoxy)phosphoryl]oxypentane
• CAS: 14254-40-1
• 化学式: C₁₀H₂₂ClO₃P
• 分子量: 256.71
• InChiKey: BTJUVGVQUQYMKY-UHFFFAOYSA-N

物化性质

• 沸点：
  141-142 °C(Press: 6 Torr)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二正戊基磷酸酯 在 potassium fluoride 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 生成 dipentyl phosphorofluoridate
  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
• 作为产物：
  描述：

  亚磷酸二戊酯 生成 二正戊基磷酸酯
  参考文献：
  名称：

  Grosse-Ruyken,H.; Uhlig,K., Journal fur praktische Chemie (Leipzig 1954), 1962, vol. 18, p. 287 - 291

  摘要：

  DOI：

文献信息

• Synthesis of Phosphorocyanidates via Phosphorochloridates
  作者：Enxue Shi、Chengxin Pei

  DOI：10.1080/10426500307856

  日期：2003.5.1

  Dialkyl phosphorocyanidates ( 2 ) were obtained from dialkyl phosphorochloridates ( 1 ) in high yield (80-86%) at room temperature in methyl cyanide. Reaction between diethyl phosphorochloridate and potassium cyanide was greatly influenced by the solvents used. Tetraethyl pyrophosphate also was found to react with potassium cyanide to give diethyl phosphorocyanidate in methyl cyanide.

  在室温下在甲基氰化物中以高产率（80-86%）从二烷基磷酰氯（1）获得二烷基磷氰（2）。所用溶剂极大地影响了二乙基氯化磷和氰化钾之间的反应。还发现焦磷酸四乙酯与氰化钾反应，在甲基氰化物中得到磷酸二乙酯。
• Convenient Preparation of Long-Chain Dialkyl Phosphates: Synthesis of Dialkyl Phosphates
  作者：R. Aitken、Chris Collett、Shaun Mesher

  DOI：10.1055/s-0031-1290823

  日期：2012.8

  Abstract Reaction of phosphorus oxychloride with a primary alcohol (1.8 equiv) and triethylamine (1.8 equiv) in toluene, followed by filtration and treatment with steam, gives dialkyl phosphates in good yield and essentially free from trialkyl phosphate contamination. Reaction of phosphorus oxychloride with a primary alcohol (1.8 equiv) and triethylamine (1.8 equiv) in toluene, followed by filtration

  摘要 氯氧化磷与伯醇（1.8当量）和三乙胺（1.8当量）在甲苯中反应，然后过滤并用蒸汽处理，得到的磷酸二烷基酯收率高，基本上没有磷酸三烷基酯的污染。 氯氧化磷与伯醇（1.8当量）和三乙胺（1.8当量）在甲苯中反应，然后过滤并用蒸汽处理，得到的磷酸二烷基酯收率高，基本上没有磷酸三烷基酯的污染。
• N,N-Dichloro poly(styrene-co-divinyl benzene) sulfonamide polymeric beads: an efficient and recyclable reagent for the synthesis of dialkyl chlorophosphates from dialkylphosphites at room temperature
  作者：Hemendra K. Gupta、Avik Mazumder、Prabhat Garg、Pranav K. Gutch、Devendra K. Dubey

  DOI：10.1016/j.tetlet.2008.09.044

  日期：2008.11

  simple method is developed for the synthesis of dialkyl chlorophosphates from dialkylphosphites using a new chlorine bearing reagent, N,N-dichloro poly(styrene-co-divinyl benzene) sulfonamide in the form of polymeric beads. The reagent afforded dialkyl chlorophosphates at room temperature, and is recyclable.

  开发了一种有效且操作简单的方法，该方法使用一种新型的含氯试剂，N，N-二氯聚（苯乙烯-共二乙烯基苯）磺酰胺，以聚合物珠粒的形式，从亚磷酸二烷基酯合成氯磷酸二烷基酯。该试剂在室温下提供了氯代磷酸二烷基酯，并且是可回收的。
• <i>N</i>-<i>tert</i>-Butyl-<i>N</i>-chlorocyanamide: A Mild and Efficient Chlorinating Agent for the Synthesis of Dialkyl/Diaryl Chlorophosphates
  作者：Vinod Kumar、Mahabir Parshad Kaushik

  DOI：10.1246/cl.2006.312

  日期：2006.3

  An efficient reagent for the synthesis of dialkyl/diaryl chlorophosphates has been developed. N-tert-Butyl-N-chlorocyanamide acts as a chlorinating agent both in polar as well in nonpolar medium and the transformation of dialkyl/diaryl phosphites to the dialkyl/diaryl chlorophosphates takes place rapidly under mild conditions in quantitative yields.

  已开发出一种用于合成二烷基/二芳基氯代磷酸酯的有效试剂。N-叔丁基-N-氯氰胺在极性和非极性介质中均用作氯化剂，亚磷酸二烷基/二芳基酯向氯磷酸二烷基/二芳基酯的转化在温和条件下以定量产率迅速发生。
• EFFICIENT AND COST-EFFECTIVE SYNTHESIS OF DIALKYL CHLOROPHOSPHATES
  作者：P. D. Shakya、D. K. Dubey、Deepak Pardasani、Meehir Palit、A. K. Gupta

  DOI：10.1080/00304940509354988

  日期：2005.12

  Organophosphorus compounds have found a wide range of applications in the areas of industrial, agricultural and medicinal chemistry owing to their biological and physical properties as well as their utility as synthetic intermediates.' Dialkyl chlorophosphates have been used in the synthesis of phosphorus based insecticides/pesticides and have also been reported as reactive intermediates or synthons for the

  有机磷化合物由于其生物学和物理特性以及它们作为合成中间体的效用，在工业、农业和药物化学领域得到了广泛的应用。氯代磷酸二烷基酯已用于合成磷基杀虫剂/杀虫剂，也被报道作为反应中间体或合成子用于转化各种官能团，如氨基磷酸酯、磷酸酯、烯醇磷酸酯、酰肼、拟卤代磷酸酯和许多其他有机磷化合物。1-9 最近，氯磷酸二乙酯已被用作环化反应和环氧化物区域选择性开环的有效试剂。*由于它们的广泛用途和我们对其性质的兴趣，我们决定重新研究它们的合成。已经开发了多种方法来从相应的亚磷酸酯（二烷基-H-膦酸酯/亚磷酸三烷基酯）与各种试剂（例如元素氯、'0 光气、”S0,C1,,'2）反应制备氯磷酸二烷基酯S,Cl,,'3 CCl,,15 CC13N0,,16 PhS0,NC1,,'7 C,C16,1s CISCC13,'9CuC12,20 perchlorofulvalene,21 和 N-氯丁二酰亚胺。在实验室中操作