N-butyl-P,P-diphenylphosphinic acid | 5756-05-8

• 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: N-butyl-P,P-diphenylphosphinic acid
• 英文别名: diphenyl butylphosphoramidate；diphenyl (n-butyl)phosphoramidate；butyl-amidophosphoric acid diphenyl ester；Butyl-amidophosphorsaeure-diphenylester；N-diphenoxyphosphorylbutan-1-amine
• CAS: 5756-05-8
• 化学式: C₁₆H₂₀NO₃P
• 分子量: 305.313
• InChiKey: LQUFYOOEPKYNTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-butyl-P,P-diphenylphosphinic acid 在 氢氧化钾 作用下， 生成 N-(n-Butyl)phosphoramidsaeure
  参考文献：
  名称：

  Structure-reactivity correlation for the hydrolysis of phosphoramidate monoanions

  摘要：

  DOI：

  10.1021/ja00745a032
• 作为产物：
  描述：

  phosphoric acid butyl ester-diphenyl ester 在 四氯化碳 、 sodium azide 、 三甲胺盐酸盐 作用下， 以 乙腈 为溶剂， 以71%的产率得到N-butyl-P,P-diphenylphosphinic acid
  参考文献：
  名称：

  Albrecht, Steffen; Herrmann, Eckhard, Zeitschrift fur Chemie, 1985, vol. 25, # 12, p. 429

  摘要：

  DOI：

文献信息

• The Step‐Wise Synthesis of Oligomeric Phosphoramidates
  作者：Shailja Data、Jeffery Leung Wai、Saawan Kumar、Alan J. Cameron、Manon Trehet、Emeka J. Itumoh、Joey Feld、Tilo Söhnel、Erin M. Leitao

  DOI：10.1002/ejoc.202101062

  日期：2021.10.26

  Ex(P−N)ding the chain. Salt elimination and lithiation strategies were employed in the step-wise synthesis of oligomers with P−N linkages having potential as environment friendly flame retardants due to their lack of anti-microbial activity.

  Ex(PN)ding 链。盐消除和锂化策略用于逐步合成具有 P-N 键的低聚物，由于它们缺乏抗微生物活性，因此具有作为环境友好型阻燃剂的潜力。
• Zinc‐catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides
  作者：Jun Ying、Qian Gao、Xiao‐Feng Wu

  DOI：10.1002/asia.202000154

  日期：2020.5.15

  We have developed a facile and efficient procedure for the synthesis of diarylphosphate esters and amides. Using Zn(acac)2 as the catalyst, the reaction of diarylphosphoryl azides with aliphatic alcohols and phenols through an unusual P-N bond cleavage provided a number of diarylphosphate esters in good yields (22 examples, up to 94%). Additionally, various diarylphosphate amides were obtained from

  我们已经开发了一种简便而有效的合成二芳基磷酸酯和酰胺的方法。使用Zn（acac）2作为催化剂，二芳基磷酰基叠氮化物与脂肪族醇和苯酚的反应通过不寻常的PN键裂解，以良好的收率提供了许多二芳基磷酸酯（22个实例，最高94％）。另外，从相应的胺也以优异的产率获得了各种二芳基磷酸酰胺（8个实例，高达96％）。
• Amide as a protecting group in phosphate ester synthesis. Part I. The acid hydrolysis of some phosphoramidic diesters
  作者：J. A. Stock、W. J. Hopwood、P. D. Regan

  DOI：10.1039/j39660000637

  日期：——

  The acid hydrolysis of a series of N-substituted diphenyl and di-n-butyl phosphoramidates has been studied. The N-methyl compounds were the most readily hydrolysed; in refluxing 25% aqueous formic acid, specific cleavage of the P–N bond was complete in a few minutes.

  已经研究了一系列N-取代的二苯基和氨基磷酸二正丁酯的酸水解。的Ñ -甲基化合物最容易水解; 在回流的25％甲酸水溶液中，PN键的特异性裂解在几分钟内完成。
• Stereospecific Aerobic Oxidative Dehydrocoupling of P(O)–H Bonds with Amines Catalyzed by Copper
  作者：Yongbo Zhou、Jia Yang、Tieqiao Chen、Shuang-Feng Yin、Daoqing Han、Li-Biao Han

  DOI：10.1246/bcsj.20130310

  日期：2014.3.15

  Copper-catalyzed stereospecific oxidative dehydrocouplings of P(O)–H bonds with amines under air took place efficiently at room temperature to afford the corresponding amidophosphorus compounds in high yields. Mechanistic studies showed that this dehydrocoupling reaction proceeded stereospecifically with inversion of stereochemistry at phosphorus.

  在空气中，铜催化的P(O)–H键与胺的立体专一性氧化脱氢偶联反应在室温下高效进行，获得了相应的氨基磷化合物，并且产率很高。机理研究表明，这一脱氢偶联反应以立体专一性的形式进行，伴随磷原子立体化学的反转。
• FLAME RETARDANT COMPRISING AROMATIC PHOSPHATE ESTER-BASED COMPOUND, AND METHOD FOR PREPARING SAME
  申请人：KWAK Seung Min

  公开号：US20150266908A1

  公开（公告）日：2015-09-24

  A method for preparing a novel aromatic phosphate ester-based compound, including: (a) reacting a compound expressed by chemical formula 1 (i) and a C 6-10 aryl compound substituted with hydroxy or C 1-6 alkoxy, or a C 6-20 arylalkyl compound substituted with hydroxy or C 1-6 alkoxy (ii), which are used as reaction materials by gradually heating to the temperature levels of 90-125° C., 125-180° C., 180-210° C. and 210-240° C.; (b) separating an aromatic phosphate ester-based compound from the resultant product in step (a) under the condition of a pressure of 0.01 mmHg-50 mmHg and a temperature of 50° C.-300° C. using fractional distillation; and (c) reacting the aromatic phosphate ester-based compound separated in step (b) (i) and C 1-10 alcohol or a nitrogen compound (ii) at a temperature of 10-70° C.

  一种制备新型芳香磷酸酯化合物的方法，包括：(a) 通过逐渐加热至90-125°C、125-180°C、180-210°C和210-240°C的温度水平，反应化学式1（i）表示的化合物和带有羟基或C1-6烷氧基取代的C6-10芳基化合物，或带有羟基或C1-6烷氧基取代的C6-20芳基烷基化合物（ii），它们作为反应材料；(b) 在0.01毫米汞柱至50毫米汞柱的压力和50°C至300°C的温度条件下，使用分馏法从步骤（a）中的产物中分离出芳香磷酸酯化合物；(c) 在10-70°C的温度下，将步骤（b）中分离出的芳香磷酸酯化合物（i）与C1-10醇或氮化合物（ii）反应。