2-phenylethyl phosphorodichloridate | 55004-22-3

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 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: 2-phenylethyl phosphorodichloridate
• 英文别名: Phenethylphosphondichlorid；(2-Phenylethyl)phosphonic dichloride；2-dichlorophosphorylethylbenzene
• CAS: 55004-22-3
• 化学式: C₈H₉Cl₂OP
• 分子量: 223.039
• InChiKey: XQANZTRSJCEURX-UHFFFAOYSA-N

物化性质

• 沸点：
  319.6±21.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenylethyl phosphorodichloridate 在 N-乙基吗啉 、 氢氧化钾 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 Nα-<(2-phenylethyl)phenoxyphosphoryl>-L-alanyl-L-proline benzyl ester
  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：

  苯乙基磷酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenylethyl phosphorodichloridate
  参考文献：
  名称：

  第二代磷 (V) 催化对映选择性亲核去对称化：提高通用性、效率和模块化

  摘要：

  用于对映选择性合成立体源磷 (V) 化合物的第二代催化两相策略。该方案由双功能亚氨基正膦 (BIMP) 催化的前手性、工作台稳定的 P(V) 前体的亲核去对称化和随后的对映特异性取代组成，允许不同地获得一系列C -、 N -、 O - 和S - 取代的 P( V) 来自少数对映体富集中间体的化合物。

  DOI：

  10.1002/anie.202400673

文献信息

• Matrix metalloproteinase inhibitors
  申请人：——

  公开号：US20020103166A1

  公开（公告）日：2002-08-01

  A compound of the general formula I 1 wherein Y is O or S; n is 1, 2, 3 or 4; X represents hydroxamic acid, carboxylic acid, phosphonic acid, acetylthiomethyl group or a mercaptomethyl group; R1 is 2 wherein E, when present represents, a bond or optionally substituted methylene or ethylene; s and t are independently 0, 1, 2 or 3; A and A′ independently represent a bond, or a saturated or unsaturated, optionally substituted cyclic or heterocyclic hydrocarbon di- or triradical; Z represents a bond, O, S, C(O), C(O)NR7, NR7C(O) or NR7, wherein R7 is hydrogen, hydroxy, branched or straight, saturated or unsaturated, optionally substituted hydrocarbon radical; R5 represents a bond, alkane or alkene diradical, one or more ether diradicals (R—O—R′) or amine diradicals (R—N—R′), wherein R and R′ independently represent alkane or alkene diradicals with a C-content from 0 to 3; R6 represents hydrogen, hydroxy, halogen, cyano, nitro, branched or straight, saturated or unsaturated, optionally substituted hydrocarbon radical, unsaturated optionally substituted cyclic or heterocyclic hydrocarbon radical, NR8R9, C(O)NR8R9, C(O)R8, CO(O)R8, S(O) 2 R9, wherein each R8 and R9 independently represent hydrogen, halogen, a branched or straight, saturated or unsaturated, optionally substituted hydrocarbon radical; R2 represents hydrogen, (C 1-8 )alkyl, (C 2-6 )alkenyl, (C 3-8 )cycloalkyl, aryl(C 0-6 )alkyl or heteroaryl(C 0-6 )alkyl; provided that if A, A′, Z and R5 are all bonds, and s and t are both 0 (zero), then R6 is different from hydrogen; or a salt, hydrate or solvate thereof. The compounds are valuable for human and veterinary therapy.

  一般式为I1的化合物，其中Y为O或S；n为1、2、3或4；X代表羟肟酸、羧酸、膦酸、乙酰硫甲基基团或巯基甲基基团；R1为2，其中E在存在时表示键或可选取代的亚甲基或乙烯基；s和t分别为0、1、2或3；A和A′分别表示键或饱和或不饱和、可选取代的环烷基或杂环烷基二元或三元基团；Z表示键、O、S、C（O）、C（O）NR7、NR7C（O）或NR7，其中R7为氢、羟基、支链或直链、饱和或不饱和、可选取代的碳氢基团；R5表示键、烷基或烯基二元基团、一个或多个醚二元基团（R—O—R′）或胺二元基团（R—N—R′），其中R和R′分别独立地表示具有0至3个碳的烷基或烯基二元基团；R6表示氢、羟基、卤素、氰基、硝基、支链或直链、饱和或不饱和、可选取代的碳氢基团、不饱和可选取代的环烷基或杂环烷基基团、NR8R9、C（O）NR8R9、C（O）R8、CO（O）R8、S（O）2R9，其中每个R8和R9独立地表示氢、卤素、支链或直链、饱和或不饱和、可选取代的碳氢基团；R2表示氢、（C1-8）烷基、（C2-6）烯基、（C3-8）环烷基、芳基（C0-6）烷基或杂环芳基（C0-6）烷基；前提是如果A、A′、Z和R5都是键，并且s和t都为0（零），则R6与氢不同；或其盐、水合物或溶剂化物。这些化合物对人类和兽医疗法有价值。
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