1-Phenylethylphosphonic acid diphenyl ester | 14295-48-8

• 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: 1-Phenylethylphosphonic acid diphenyl ester
• 英文别名: (2-phenylethyl)phosphonic acid diphenyl ester；phenethyl-phosphonic acid diphenyl ester；Phenaethyl-phosphonsaeure-diphenylester；2-Diphenoxyphosphorylethylbenzene
• CAS: 14295-48-8
• 化学式: C₂₀H₁₉O₃P
• 分子量: 338.343
• InChiKey: CEFLMOHDLFCEQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-Phenylethylphosphonic acid diphenyl ester 在 氢氧化钾 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 phenyl (2-phenylethyl)-phosphonochloridate
  参考文献：
  名称：

  N.alpha.-(O,O'-Diphenoxyphosphoryl)-L-alanyl-L-proline, N.alpha.-[O,O'-bis(4-nitrophenoxy)phosphoryl]-L-alanyl-L-proline and N.alpha.-[P-(2-phenylethyl)-O-phenoxyphosphoryl]-L-alanyl-L-proline: releasers of potent inhibitors of angiotensin converting enzyme at physiological pH and temperature

  摘要：

  The rate of loss of phenol or 4-nitrophenol from N alpha-(diphenoxyphosphoryl)-L-alanyl-L-proline (2), N alpha-[bis(4-nitrophenoxy)phosphoryl]-L-alanyl-L-proline (5), and N alpha-[(2-phenylethyl)phenoxyphosphoryl]-L-alanyl-L-proline (12) was determined spectrophotometrically at pH 7.5 and 37 degrees C in both Tris and phosphate buffers. These moderately potent inhibitors of angiotensin converting enzyme (Ki greater than 0.8 microM) all hydrolyze, losing 1 mol of phenol to yield highly potent inhibitors (Ki = 0.5-18 nM). The half-times for loss of 1 mol of phenol in Tris buffer are 22 days (2), 3.4 h (5), and 21 days (12). The half-times in phosphate buffer were not significantly different. The mono(4-nitrophenoxy) ester 6 (Ki = 18 nM) loses its 1 mol of nitrophenol with a half-time of 35 h to yield N alpha-phosphoryl-L-alanyl-L-proline 16 (Ki = 1.4 nM), which hydrolyzes at the P-N bond with a half-time of 2.2 h. Hydrolysis of the P-N bond in 2 and 12 was not observed during the time course of the kinetic experiments. The two phosphoramidate diesters 2 and 5 and the phosphonamidate monoester 12 thus release powerful inhibitors of angiotensin converting enzyme with a known time course at physiological pH and temperature in vitro. A time-dependent increase in inhibitory potency against converting enzyme that paralleled the kinetics of phenyl ester hydrolysis was confirmed in vitro.

  DOI：

  10.1021/jm00148a008
• 作为产物：
  描述：

  diphenyl (E)-styrylphosphonate 在 <((t-Bu)2PH)PdP(t-Bu)2>2 (pretreated with oxygen) 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以57%的产率得到1-Phenylethylphosphonic acid diphenyl ester
  参考文献：
  名称：

  Palladium Catalyzed Hydrogenation of .alpha.,.beta.-Unsaturated Sulfones and Phosphonates

  摘要：

  The binuclear palladium complex, [(Bu(2)(t)PH)-PdPBu(2)(t)](2), when treated with oxygen, catalyzes the hydrogenation of the double bond of alpha,beta-unsaturated sulfones and phosphonates in THF at room temperature and 1 atm of hydrogen pressure. Saturated sulfones and phosphonates were isolated in 49-93% yields.

  DOI：

  10.1021/jo00094a001

文献信息

• Regioselective C-Acylation of Vinylphosphorus Compounds Through Electroreduction or Mg-Promoted Reduction
  作者：Makoto Kyoda、Takamichi Yokoyama、Hirofumi Maekawa、Toshinobu Ohno、Ikuzo Nishiguchi

  DOI：10.1055/s-2001-17471

  日期：——

  Either of electroreduction or Mg-promoted electron-transfer reaction of vinylphosphonate derivatives 1-4 in the presence of acid anhydrides 5 a - c or acid chlorides 15 b, c brought about regioselective C-acylation to give the corresponding β-acylphosphonates 3 in good yields. The reaction may be initiated through one-electron transfer from either a cathode or Mg metal to a substrate to give the corresponding anion radical, which is then subjected to electrophilic attack of an acylating agent, followed by the fast second electron-transfer.

  在酸酐5a-c或酰氯15b、c的存在下，乙烯膦酸酯衍生物1-4无论是通过电还原还是Mg促进的电子转移反应，均能选择性地发生C-酰化反应，得到相应的β-酰基膦酸酯3，产率良好。反应可能始于从一个阴极或Mg金属向底物的一次电子转移，生成相应的阴离子自由基，随后遭受酰化剂的亲电攻击，继而迅速进行第二次电子转移。
• Mechanism of the Michaelis-Arbuzov Reaction: Olefin Formation
  作者：ALBERT Y. GARNER、EARL C. CHAPIN、PATRICIA M. SCANLON

  DOI：10.1021/jo01086a023

  日期：1959.4
• A process for the preparation of thermoplastic polyphosphonatophenyl ester carbonates
  申请人：MOBAY CORPORATION

  公开号：EP0077488B1

  公开（公告）日：1986-09-10
• US4322520A
  申请人：——

  公开号：US4322520A

  公开（公告）日：1982-03-30
• US4381390A
  申请人：——

  公开号：US4381390A

  公开（公告）日：1983-04-26