2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid | 86963-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid
• 英文别名: 2-diethoxyphosphoryl-3-(4-methoxyphenyl)propanoic acid
• CAS: 86963-63-5
• 化学式: C₁₄H₂₁O₆P
• 分子量: 316.291
• InChiKey: UKHYMEWOWLSHLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid 在 氯化亚砜 、 sodium azide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 Azoture de l'acide 2-diethylphosphono-3-(4-methoxy)phenylpropanoique
  参考文献：
  名称：

  Synthese de peptides modifies incorporant un motif phosphore n ou c terminal

  摘要：

  A general route to phosphopeptids with a 2-oxoalkylphosphonate moiety at the terminal N-aminogroup or with a 1-aminoalkylphosphonate moiety at the terminal C-carboxyl group is described. The method allows the preparation of various phosphopeptids with an alpha-alkylated carbon atom on the P-C bond from the very available dialkylphosphonoalcanoic acids as starting products.

  DOI：

  10.1016/s0040-4020(01)92278-1
• 作为产物：
  描述：

  ethyl 2-(diethoxyphosphoryl)-3-(4-methoxyphenyl)propanoate 、 氢氧化锂 生成 2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid
  参考文献：
  名称：

  WILKINSON, S.;WRIGGLESWORTH, R.;HARDY, G. W.

  摘要：

  DOI：

文献信息

• Pharmaceutical amides, and preparation, formulations and use of thereof
  申请人：The Wellcome Foundation Ltd.

  公开号：US04423242A1

  公开（公告）日：1983-12-27

  Compounds of the general formula ##STR1## wherein Ph is a phenyl group which is optionally substituted by one or more substituents selected from halo (i.e. fluoro, chloro, bromo or iodo), C.sub.1-4 alkyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, nitro, sulphonyl, aminosulphonyl, trihalomethyl, carboxy, C.sub.1-4 alkoxycarbonyl, amido, C.sub.1-4 alkylamido C.sub.1-4 alkoxy, C.sub.2-4 alkenyl, cyano, aminomethyl or methylsulphonyl; R.sup.a and R.sup.b, which may be the same or different, each represents a hydrogen or alkali metal (e.g. sodium or lithium) atom or a C.sub.1-4 (e.g. ethyl) group; m is 0 or 1; Y is a group of formula: --NH--CH.sub.2 --CO-- or a group of formula: ##STR2## where R.sup.1 is hydrogen or methyl; R.sup.2 is alkyl of 1 to 3 carbon atoms or is methylthiomethyl; and Z is --OR.sup.3 or --NR.sup.4 R.sup.5 where R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or alkyl of 1 to 4 carbon atoms (i.e. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or t-butyl) and R.sup.3 can further be phenylalkyl having 1 to 3 carbon atoms in the alkylene moiety thereof, or phenyl; and basic salts thereof. These compounds have an advantageous enkephalinase inhibitory activity which renders the compounds useful in medical therapy, e.g. to prolong and/or potentiate in a mammal, the effects of endogenous or exogenous enkephalins. The latter includes synthetic enkepalin analogues.

  一般式为##STR1##的化合物，其中Ph是苯基，可选地取代为一个或多个取代基，所选取代基包括卤素（即氟、氯、溴或碘）、C.sub.1-4烷基、氨基、C.sub.1-4烷基氨基、二-C.sub.1-4烷基氨基、硝基、磺酰基、氨基磺酰基、三卤甲基、羧基、C.sub.1-4烷氧基羰基、酰胺基、C.sub.1-4烷基酰胺基、C.sub.1-4烷氧基、C.sub.2-4烯基、氰基、氨甲基或甲磺酰基；R.sup.a和R.sup.b，可以相同也可以不同，分别代表氢或碱金属（例如钠或锂）原子或C.sub.1-4（例如乙基）基团；m为0或1；Y是公式：--NH--CH.sub.2 --CO--或公式：##STR2##的基团，其中R.sup.1是氢或甲基；R.sup.2是1至3个碳原子的烷基或甲基硫代甲基；Z是--OR.sup.3或--NR.sup.4 R.sup.5，其中R.sup.3、R.sup.4和R.sup.5分别是氢或1至4个碳原子的烷基（即甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基），并且R.sup.3还可以是具有1至3个碳原子的烷基链的苯基烷基，或苯基；以及它们的盐。这些化合物具有有利的脑啡肽酶抑制活性，使得这些化合物在医疗治疗中有用，例如在哺乳动物中延长和/或增强内源性或外源性脑啡肽的效果，后者包括合成的脑啡肽类似物。
• Pharmaceutical compounds, and preparation, formulations and use thereof
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0075334A2

  公开（公告）日：1983-03-30

  Compounds of the general formula wheren Ph is a phenyl group which is optionally substituted by one or more substituents selected from halo (i.e. fluoro, chloro, bromo or iodo), C1-4alkyl, amino, C1-4alkylamino, di-C1-4alkylamino, nitro, sulphonyl, aminosulphonyl, trihalomethyl, carboxy, C1-4alkoxycarbonyl, amido, C1-4alky(amido C1-4alkoxy, C2-4alkenyl, cyano, aminomethyl or methylsulphonyl; R' und Rb, which may be the same or different, each represents a hydrogen or alkali metal (eg. sodium or lithium) atom or a C1-4 (eg. ethyl) group; m is 0 or 1; Y is a group of formula: or a group of formula: where R' is hydrogen or methyl; R2 is alkyl of 1 to 3 carbon atoms or is methylthiomethyl; and Z is -OR3 or -NR4Rs where R3, R4 and R5 are each hydrogen or alkyl of 1 to 4 carbon atoms (ie. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or t-butyl) and R3 can further be phenylalkyl having 1 to 3 carbon atoms in the alkylene moiety thereof, or phenyl; and basic salts thereof. These compounds have an advantageous enkephalinase inhibitor activity which renders the compounds useful in medical therapy, eg. to prolong and/or potentiate in a mammal, the effects of endogenous or exogenous enkephalins. The latter includes synthetic enkephalin analogues.

  通式如下的化合物 其中 Ph 是苯基，可任选被一个或多个取代基取代，这些取代基选自卤代（即C1-4烷基、氨基、C1-4烷基氨基、二-C1-4烷基氨基、硝基、磺酰基、氨磺酰基、三卤甲基、羧基、C1-4烷氧基羰基、氨基、C1-4烷氧基、C2-4烯基、氰基、氨甲基或甲基磺酰基；R'和 Rb 可以相同或不同，各自代表氢原子或碱金属（如钠或锂）原子或 C1-4（如乙烯基）原子。m为 0 或 1； Y 是式中的基团 或式 其中 R' 是氢或甲基； R2 是 1 至 3 个碳原子的烷基或甲硫基；以及 Z是-OR3或-NR4Rs，其中R3、R4和R5各自是氢或1至4个碳原子的烷基（即甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基），R3还可以是在其亚烷基中具有1至3个碳原子的苯基烷基或苯基；以及它们的碱式盐。这些化合物具有良好的脑啡肽酶抑制剂活性，可用于医学治疗，例如延长和/或增强哺乳动物体内的内源性或外源性脑啡肽的作用。后者包括合成的脑啡肽类似物。
• WILKINSON, S.;WRIGGLESWORTH, R.;HARDY, G. W.
  作者：WILKINSON, S.、WRIGGLESWORTH, R.、HARDY, G. W.

  DOI：——

  日期：——
• US4423242A
  申请人：——

  公开号：US4423242A

  公开（公告）日：1983-12-27
• Synthese de peptides modifies incorporant un motif phosphore n ou c terminal
  作者：Ph. Coutrot、C. Grison、C. Charbonnier-Gérardin

  DOI：10.1016/s0040-4020(01)92278-1

  日期：1992.11

  A general route to phosphopeptids with a 2-oxoalkylphosphonate moiety at the terminal N-aminogroup or with a 1-aminoalkylphosphonate moiety at the terminal C-carboxyl group is described. The method allows the preparation of various phosphopeptids with an alpha-alkylated carbon atom on the P-C bond from the very available dialkylphosphonoalcanoic acids as starting products.