Anilino-phosphorsaeure-dibutylester | 13024-84-5

• 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
• 英文名称: Anilino-phosphorsaeure-dibutylester
• 英文别名: Phosphorsaeuredibutylesteranilid；(BuO)2P(O)NHC6H5；phenyl-amidophosphoric acid dibutyl ester；Phenyl-amidophosphorsaeure-dibutylester；Phosphoramidic acid, phenyl-, dibutyl ester；N-dibutoxyphosphorylaniline
• CAS: 13024-84-5
• 化学式: C₁₄H₂₄NO₃P
• 分子量: 285.323
• InChiKey: IORDJEXCQVLCGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090

反应信息

• 作为产物：
  描述：

  三丁基,三丁酯 在 四氯化碳 、 aniline hydrochloride 、 三乙胺 作用下， 生成 Anilino-phosphorsaeure-dibutylester
  参考文献：
  名称：

  Riesel, Lothar; Herrmann, Eckhard; Steinbach, Joerg, Phosphorus and Sulfur and the Related Elements, 1983, vol. 18, p. 253 - 258

  摘要：

  DOI：

文献信息

• Kinetics and Mechanism of the Anilinolysis of Dibutyl Chlorothiophosphate in Acetonitrile
  作者：Md. Ehtesham Ul Hoque、Hai-Whang Lee

  DOI：10.5012/bkcs.2012.33.3.843

  日期：2012.3.20

  The nucleophilic substitution reactions of dibutyl chlorothiophosphate (4S) with substituted anilines ($XC_6H_4NH_2$) and deuterated anilines ($XC_6H_4ND_2$) are investigated kinetically in acetonitrile at $55.0^\circ}C$. The obtained deuterium kinetic isotope effects (DKIEs;$k_H/k_D$) are primary normal ($k_H/k_D$ = 1.10-1.35). A concerted mechanism involving predominant frontside nucleophilic attack is proposed on the basis of the primary normal DKIEs and selectivity parameters. Hydrogen bonded, four-center-type transition state is proposed. The steric effects of the two ligands on the anilinolysis rates of the chlorothiophosphates are discussed. The anilinolyses of P=S systems are compared with those of their P=O counterparts on the basis of the reactivities, thio effects, selectivity parameters, and DKIEs.

  丁基氯硫酯（4S）与取代苯胺（$XC_6H_4NH_2$）和重氘取代苯胺（$XC_6H_4ND_2$）的亲核取代反应在<越南>$55.0^\circ}C$的乙腈中进行了动力学研究。获得的氘动力学同位素效应（DKIEs；$k_H/k_D$）为一级正常型（$k_H/k_D$ = 1.10-1.35）。根据一级正常DKIEs和选择性参数，提出了一种以前侧亲核攻击为主的协同机制。提出了氢键结合的四中心型过渡态。讨论了两种配体对氯硫磷酸酯苯胺水解速率的立体效应。在反应性、硫效应、选择性参数和DKIEs的基础上，比较了P=S系统的苯胺水解与其P=O对应物的苯胺水解。
• Kinetics and Mechanism of Anilinolysis of Phenyl N-Phenyl Phosphoramidochloridate in Acetonitrile
  作者：Md. Ehtesham Ul Hoque、Hai-Whang Lee

  DOI：10.5012/bkcs.2012.33.10.3274

  日期：2012.10.20

  reactions of phenyl N-phenyl phosphoramidochloridate (8) with substituted anilines () and deuterated anilines () have been carried out in acetonitrile at . The obtained deuterium kinetic isotope effects (DKIEs; ) are huge secondary inverse ( = 0.52-0.69). A concerted mechanism is proposed with a backside attack transition state (TS) on the basis of the secondary inverse DKIEs and the variation trends of the

  N-苯基氨基氯酸苯酯 (8) 与取代苯胺 () 和氘代苯胺 () 反应的动力学研究已在乙腈中进行。获得的氘动力学同位素效应 (DKIEs;) 是巨大的二次逆 (= 0.52-0.69)。基于二次逆 DKIE 和值随 X 的变化趋势，提出了一种具有背面攻击过渡态 (TS) 的协同机制。考虑到非常小的值，TS 中的键形成程度非常广泛的 DKIE。在 Taft 方程的基础上，针对氯磷酸盐型底物的氨解，广泛讨论了两种配体对速率的空间效应。
• Kinetics and Mechanism of the Anilinolysis of Dibutyl Chlorophosphate in Acetonitrile
  作者：Md. Ehtesham Ul Hoque、Hai-Whang Lee

  DOI：10.5012/bkcs.2012.33.2.663

  日期：2012.2.20

  ligands on the anilinolysis rates of the chlorothiophosphates are discussed. The anilinolysesof P=S systems are compared with those of their P=O counterparts on the basis of the reactivities, thio effects,selectivity parameters, and DKIEs.Key Words : Thiophosphoryl transfer reaction, Anilinolysis, Dibutyl chlorothiophosphate, Deuterium kineticisotope effectIntroductionThe kinetics and mechanism of the phosphoryl

  = 1.10-1.35)。在初级正态DKIEs和选择性参数的基础上，提出了一种涉及主要正面亲核攻击的协同机制。提出了氢键、四中心型过渡态。讨论了两种配体对氯代硫代磷酸酯苯胺分解速率的空间效应。从反应活性、硫代效应、选择性参数和 DKIE 等方面比较了 P=S 体系的苯胺裂解与 P=O 对应体系的苯胺裂解。本实验室对涉及四配位磷原子的磷酰基和硫代磷酰基转移反应进行了广泛研究。
• Preparation of Some Organophosphorus Compounds¹
  作者：Dasu Ramaswami、Ernst R. Kirch

  DOI：10.1021/ja01103a535

  日期：1953.4
• The Phosporylation of Aniline Derivatives in Biphase Systems
  作者：Gheorghe Ilia、Mihaela Petric、Lavinia Macarie、Smaranda Iliescu、Adriana Popa

  DOI：10.1080/10426500500536614

  日期：2006.6.1

  Aniline derivatives were phosphorylated in biphase systems using three methods. A comparative study was performed. The best results were obtained when a solid-liquid system was used. This method is the easiest and lead to higher yields (54-81%).