4-hydroxybutyl ethyl(2-cyanoethyl)phosphinate

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦酸及其衍生物
• 英文名称: 4-hydroxybutyl ethyl(2-cyanoethyl)phosphinate
• 英文别名: 4-Hydroxybutyl ethyl(2-cyanoethyl)phosphinate；3-[ethyl(4-hydroxybutoxy)phosphoryl]propanenitrile
• 化学式: C₉H₁₈NO₃P
• 分子量: 219.221
• InChiKey: WZASQTVUHJUYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-丁二醇 、 ethyl(2-cyanoethyl)phosphinic acid 在 水 、 甲苯 、 乙二醇乙醚 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以to leave 604 g (92% of theory) of 4-hydroxybutyl ethyl(2-cyanoethyl)phosphinate as colorless oil的产率得到4-hydroxybutyl ethyl(2-cyanoethyl)phosphinate
  参考文献：
  名称：

  Method for Producing Mono-Aminofunctionalized Dialkylphosphinic Acids and Esters and Salts Thereof by Means of Acrylnitriles and Use Thereof

  摘要：

  本发明涉及一种通过丙烯腈制备单氨基功能化二烷基膦酸和酯及其盐的方法，其特征在于：a）在催化剂A的存在下，将膦酸源（I）与烯烃（IV）反应，得到烷基膦酸盐或酯（II）；b）在催化剂B的存在下，将所得的烷基膦酸盐或酯（II）与式（V）的丙烯腈反应，得到一种单功能化的二烷基膦酸衍生物（VI）；c）在催化剂C或还原剂的存在下，将所得的单功能化的二烷基膦酸衍生物（VI）反应，得到一种单氨基功能化的二烷基膦酸衍生物（III）。其中，R1、R2、R3、R4、R5、R6、R7相同或不同且独立地代表H、C1-C18烷基、C6-C18芳基、C6-C18芳基烷基、C6-C18烷基芳基，X代表H、C1-C18烷基、C6-C18芳基、C6-C18芳基烷基、C6-C18烷基芳基、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K和/或质子化氮碱，Y代表矿酸、羧酸、路易斯酸或有机酸，n为0到4的整数或分数，催化剂A和C由过渡金属、过渡金属化合物和/或由过渡金属和/或过渡金属化合物和至少一种配体组成的催化剂体系形成，催化剂B由形成过氧化物、过氧化物化合物、偶氮化合物、碱金属、碱土金属、碱金属氢化物、碱土金属氢化物和/或碱金属醇盐和碱土金属醇盐的化合物组成。

  公开号：

  US20110213078A1

文献信息

• Method for Producing Mono-Aminofunctionalized Dialkylphosphinic Acids and Esters and Salts Thereof and Use Thereof
  申请人：Hill Michael

  公开号：US20110213061A1

  公开（公告）日：2011-09-01

  The invention relates to a method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with a hydrogen cyanide source to yield a mono-functionalized dialkylphosphinic acid derivative (VII) in the presence of a catalyst C, and d) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VII); is reacted to yield a mono-aminofunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst D or a reduction agent, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are the same or different and stand independently of each other, among other things, for H, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 6 -C 18 aralkyl, C 6 -C 18 alkylaryl, and X stands for H, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 6 -C 18 aralkyl, C 6 -C 18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and Y stands for a mineral acid, a carboxylic acid, a Lewis acid or an organic acid, n=0 to 4 and the catalysts A, B, C and D are formed by transition metals, transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand.

  本发明涉及一种生产单氨基功能化二烷基膦酸和酯及其盐的方法，其特征在于：a）在催化剂A的存在下，将膦酸源（I）与烯烃（IV）反应，得到烷基膦酸盐或酯（II）；b）在催化剂B的存在下，将所得的烷基膦酸盐或酯（II）与式（V）的乙炔化合物反应，得到单官能化的二烷基膦酸衍生物（VI）；c）在催化剂C的存在下，将所得的单官能化的二烷基膦酸衍生物（VI）与氰化氢源反应，得到单官能化的二烷基膦酸衍生物（VII）；d）在催化剂D或还原剂的存在下，将所得的单官能化的二烷基膦酸衍生物（VII）反应，得到单氨基功能化的二烷基膦酸衍生物（III）。其中，R1、R2、R3、R4、R5、R6可以相同或不同，独立地代表H、C1-C18烷基、C6-C18芳基、C6-C18芳基烷基、C6-C18烷基芳基，X代表H、C1-C18烷基、C6-C18芳基、C6-C18芳基烷基、C6-C18烷基芳基、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K和/或质子化的氮碱基，Y代表矿酸、羧酸、Lewis酸或有机酸，n=0至4，催化剂A、B、C和D由过渡金属、过渡金属化合物和/或由过渡金属和/或过渡金属化合物和至少一种配体组成的催化剂体系形成。
• Method for Producing Mono-Carboxyfunctionalized Dialkylphosphinic Acids and Esters and Salts Thereof by means of Vinylenes-Nitriles and Use Thereof
  申请人：Hill Michael

  公开号：US20110213059A1

  公开（公告）日：2011-09-01

  The invention relates to a method for producing mono-carboxyfunctional zed dialkylphosphinic acids and esters and salts thereof by means of vinylenes/nitriles, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with a hydrogen cyanide source to yield a mono-functionalized dialkylphosphinic acid derivative (VII) in the presence of a catalyst C, and d) the thus obtained monofunctionalized dialkylphosphinic acid derivative (VII); is reacted to yield a monocarboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst D, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are the same or different and stand independently of each other, among other things, for H, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 6 -C 18 aralkyl, C 6 -C 18 alkylaryl, and X and Y are the same or different and stand independently of each other for H, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 6 -C 18 aralkyl, C 6 -C 18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalysts A, B and C are formed by transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and the catalyst D is an acid or a base.

  本发明涉及一种通过使用乙烯基/腈类化合物制备单羧基取代的二烷基膦酸和酯及其盐的方法，其特征在于a）在催化剂A的存在下，将膦酸源（I）与烯烃（IV）反应，得到烷基膦酸，盐或酯（II）；b）在催化剂B的存在下，将所得的烷基膦酸，盐或酯（II）与式（V）的炔烃化合物反应，得到单功能化的二烷基膦酸衍生物（VI）；c）在催化剂C的存在下，将所得的单功能化的二烷基膦酸衍生物（VI）与氰化氢源反应，得到单功能化的二烷基膦酸衍生物（VII）；d）在催化剂D的存在下，将所得的单功能化的二烷基膦酸衍生物（VII）反应，得到单羧基取代的二烷基膦酸衍生物（III）。其中，R1，R2，R3，R4，R5，R6相同或不同且独立地代表H，C1-C18烷基，C6-C18芳基，C6-C18芳基烷基，C6-C18烷基芳基，X和Y相同或不同且独立地代表H，C1-C18烷基，C6-C18芳基，C6-C18芳基烷基，C6-C18烷基芳基，Mg，Ca，Al，Sb，Sn，Ge，Ti，Fe，Zr，Zn，Ce，Bi，Sr，Mn，Cu，Ni，Li，Na，K和/或质子化氮碱，催化剂A，B和C由过渡金属和/或过渡金属化合物和/或由过渡金属和/或过渡金属化合物和至少一种配体组成，催化剂D是酸或碱。
• Method for Producing Mono-Aminofunctionalized Dialkylphosphinic Acids and Esters and Salts Thereof by Means of Acrylnitriles and Use Thereof
  申请人：Hill Michael

  公开号：US20110213078A1

  公开（公告）日：2011-09-01

  The invention relates to a method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof by means of acrylnitriles, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with an acrylnitrile of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted to yield a mono-aminofunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C or a reduction agent, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different and stand independently of each other, among other things, for H, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 6 -C 18 aralkyl, C 6 -C 18 alkylaryl and X stands for H, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 6 -C 18 aralkyl, C 6 -C 18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and Y stands for a mineral acid, a carboxylic acid, a Lewis acid or an organic acid, n=an integer or fractional number of 0 to 4 and the catalysts A and C are formed by transition metals, transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and catalyst B is formed by compounds forming peroxides, peroxo compounds, azo compounds, alkali metals, alkaline earth metals, alkali hydrides, alkaline earth hydrides and/or alkali alcoholates and alkaline earth alcoholates.

  本发明涉及一种通过丙烯腈制备单氨基功能化二烷基膦酸和酯及其盐的方法，其特征在于：a）在催化剂A的存在下，将膦酸源（I）与烯烃（IV）反应，得到烷基膦酸盐或酯（II）；b）在催化剂B的存在下，将所得的烷基膦酸盐或酯（II）与式（V）的丙烯腈反应，得到一种单功能化的二烷基膦酸衍生物（VI）；c）在催化剂C或还原剂的存在下，将所得的单功能化的二烷基膦酸衍生物（VI）反应，得到一种单氨基功能化的二烷基膦酸衍生物（III）。其中，R1、R2、R3、R4、R5、R6、R7相同或不同且独立地代表H、C1-C18烷基、C6-C18芳基、C6-C18芳基烷基、C6-C18烷基芳基，X代表H、C1-C18烷基、C6-C18芳基、C6-C18芳基烷基、C6-C18烷基芳基、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K和/或质子化氮碱，Y代表矿酸、羧酸、路易斯酸或有机酸，n为0到4的整数或分数，催化剂A和C由过渡金属、过渡金属化合物和/或由过渡金属和/或过渡金属化合物和至少一种配体组成的催化剂体系形成，催化剂B由形成过氧化物、过氧化物化合物、偶氮化合物、碱金属、碱土金属、碱金属氢化物、碱土金属氢化物和/或碱金属醇盐和碱土金属醇盐的化合物组成。
• VERFAHREN ZUR HERSTELLUNG VON MONO-AMINOFUNKTIONALISIERTEN DIALKYLPHOSPHINSÄUREN, DEREN SALZE UND ESTER UND IHRE VERWENDUNG
  申请人：Clariant International Ltd.

  公开号：EP2352736A1

  公开（公告）日：2011-08-10
• VERFAHREN ZUR HERSTELLUNG VON MONO-CARBOXYFUNKTIONALISIERTEN DIALKYLPHOSPHINSÄUREN, -ESTERN UND -SALZEN MITTELS VINYLEN/NITRILEN UND IHRE VERWENDUNG
  申请人：Clariant International Ltd.

  公开号：EP2352738A1

  公开（公告）日：2011-08-10