N-(乙氧基-氟磷酰)-N-甲基甲胺 | 358-29-2

• 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: N-(乙氧基-氟磷酰)-N-甲基甲胺
• 英文名称: Ethoxy-dimethylamino-phosphorylfluorid
• 英文别名: phosphoric acid ethyl ester-dimethylamide fluoride；Phosphorsaeure-aethylester-dimethylamid-fluorid；Phosphoramidofluoridic acid, dimethyl-, ethyl ester；N-[ethoxy(fluoro)phosphoryl]-N-methylmethanamine
• CAS: 358-29-2
• 化学式: C₄H₁₁FNO₂P
• 分子量: 155.109
• InChiKey: JYXIMOLVBWANAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  N-(乙氧基-氟磷酰)-N-甲基甲胺 、 双(二甲胺基)氯酸磷 生成 diphosphoric acid tris-dimethylamide fluoride
  参考文献：
  名称：

  DE918603

  摘要：

  公开号：
• 作为产物：
  描述：

  3-[(4-氨基苯基)磺酰基]苯胺 在 乙醇 作用下， 生成 N-(乙氧基-氟磷酰)-N-甲基甲胺
  参考文献：
  名称：

  Schrader, Angewandte Chemie, 1952, vol. 62, p. 15

  摘要：

  DOI：

文献信息

• Effect of the structure of phosphylating agents on their reaction with ethanolamine, an ambident nucleophile
  作者：R. Greenhalgh、R. M. Heggie、M. A. Weinberger

  DOI：10.1139/v70-223

  日期：1970.5.1

  The reactions of a series of phosphylating agents (RR′P(O)X) with ethanolamine have been examined, and relative yields of the products from the nucleophilic amino and hydroxyl moieties determined. In general the amount of O-phosphylation increased as R and R′ were changed from dimethylamino through alkoxy to methyl and as the leaving group (X) was changed from OP(O)RR′ to CN. The only exceptions occurred when R was dimethylamino and X was Cl. When X was F, only O-phosphylation was observed. Thus, a wide range of essentially continuously varying selectivities was found.The results are discussed in terms of the amount of charge transfer involved in the formation of the transition state which is assumed to be determined by the electrophile. When the charge transfer is small, the contributions to the activation energy of such factors as solvation and ionization potential of the nucleophile are most important, resulting in N-phosphylation. As the amount of charge transfer increases, the energy of bond formation becomes the dominant factor and O-phosphylation is preferred.

  一系列磷酰化试剂（RR′P(O)X）与乙醇胺的反应已经被研究，确定了来自亲核氨基和羟基的产物的相对产率。一般来说，当R和R′从二甲胺基经过烷氧基变化到甲基时，O-磷酰化的量会增加，当离去基团（X）从OP(O)RR′变化为CN时也会增加。唯一的例外是当R为二甲胺基且X为Cl时。当X为F时，只观察到O-磷酰化。因此，发现了一系列基本连续变化的选择性。结果讨论了在形成过渡态时涉及的电荷转移量，该量被认为由亲电试剂决定。当电荷转移量较小时，诸如溶剂化和亲核试剂的电离势等因素对激活能的贡献最为重要，导致N-磷酰化。随着电荷转移量的增加，键合能量成为主导因素，O-磷酰化更为优先。
• Cook et al., Journal of the Chemical Society, 1949, p. 2921,2925
  作者：Cook et al.

  DOI：——

  日期：——
• Schrader, Angewandte Chemie, 1952, vol. 62, p. 15
  作者：Schrader

  DOI：——

  日期：——
• DE918603
  申请人：——

  公开号：——

  公开（公告）日：——