trans-crotyl pivalate | 119819-14-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-crotyl pivalate
• 英文别名: [(E)-but-2-enyl] 2,2-dimethylpropanoate
• CAS: 119819-14-6
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: QWPBIBFAFGOWLK-AATRIKPKSA-N

物化性质

• 沸点：
  184.3±9.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  magnesium,6-methoxy-2H-naphthalen-2-ide,bromide 、 trans-crotyl pivalate 以18%的产率得到
  参考文献：
  名称：

  HIYAMA, TAMEJIRO;WAKASA, NORIKO, TETRAHEDRON LETT., 1985, 26, N 27, 3259-3262

  摘要：

  DOI：
• 作为产物：
  描述：

  特戊酸钠 、 碳酸乙酯1-甲基烯丙基酯 在 [(η³-allyl)Pd((S)-2-Ph2P-2'-Ph2P(S)-1,1'-binaphthyl)]SbF6 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 trans-crotyl pivalate 、 、
  参考文献：
  名称：

  Enantioselective synthesis of acyclic allylic esters catalyzed by a palladium/BINAP(S) system

  摘要：

  The synthesis of chiral nonracemic acyclic allylic pivalates via the Pd-catalyzed allylic substitution of racemic allylic carbonates is presented. Good to excellent enantioselectivities (up to 90%) were observed in several cases. An extraordinarily high preference for the production of the branched regioisomeric product is seen when starting from 3-buten-2-yl and crotyl substrates. A significant kinetic resolution (k(rel) = 38) of the 1,3-dimethylallyl substrate was also observed, leading to the production of esters of both enantiomers of an allylic alcohol with a single enantiomer of catalyst. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.105

文献信息

• Method for Producing Mono-Carboxy-Functionalized Dialkylphosphinic Acids, Esters and Salts Using a Vinyl Ester of a Carboxylic Acid and the Use Thereof
  申请人：Hill Michael

  公开号：US20110237721A1

  公开（公告）日：2011-09-29

  The invention relates to a method for producing mono-carboxy-functionalized dialkyiphosphinic acids, esters and salts using a vinyl ester of a carboxylic acid. The method is characterized by the following steps: a) reacting a phosphinic acid source (I) with olefins (IV) in the presence of a catalyst A to give an alkylphosphinic acid, the salt or the ester (II) thereof, b) reacting the alkylphosphinic acid so obtained, the salt or the ester (II) thereof with a vinyl ester of a carboxylic acid of formula (V) in the presence of a catalyst B to give a mono-functionalized dialkylphosphinic acid derivative (VI) and c) reacting the mono-functionalized dialkyiphosphinic acid derivative (VI) so obtained in the presence of a catalyst C to give a mono-functionalized dialkylphosphinic acid derivative (VII) and d) reacting the mono-functionalized dialkyiphosphinic acid derivative (VII); with an oxidant or in the presence of a catalyst D to give a mono-carboxy-functionalized dialkylphosphinic acid derivative (III), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are the same or different and independently of each other inter alia represent 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 independently of each other represent H, C 1 -C 18 alkyl, C 8 -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 protonated nitrogen base and the catalysts A and D are transition metals and/or transition metal compounds and/or catalyst systems which are composed of a transition metal and/or a transition metal compound and at least one ligand, and the catalyst B is a peroxide-forming compound and/or a peroxo compound and/or an azo compound, and the catalyst C is an acid or a base.

  本发明涉及一种使用羧酸乙烯酯制备单羧基功能化二烷基膦酸、酯和盐的方法。该方法的特点在于以下步骤：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、其盐或酯（II），b）在催化剂B的存在下，将所得的烷基膦酸、其盐或酯（II）与式（V）的羧酸乙烯酯反应，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）反应，得到单功能化的二烷基膦酸衍生物（VII），d）在氧化剂的存在下或在催化剂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，得到单羧基功能化的二烷基膦酸衍生物（III），其中R1、R2、R3、R4、R5、R6相同或不同，独立地表示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，独立地表示H、C1-C18烷基、C8-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和D是过渡金属和/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的催化剂体系，催化剂B是过氧化物形成化合物和/或过氧化物和/或偶氮化合物，催化剂C是酸或碱。
• Method for the Production of Monofunctionalized Dialkylphosphinic Acids, Esters and Salts, and Use Thereof
  申请人：Hill Michael

  公开号：US20110251315A1

  公开（公告）日：2011-10-13

  The invention relates to a method for producing monofunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester thereof, whereupon said alkylphosphonous acid, the salt or ester (II) thereof is reacted with compounds containing C═C, C═O, or C═N double bonds to obtain compounds of type (III), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are identical or different from each other and independently represent, inter alia, H, C 1 -C 18 -alkyl, C 6 -C 18 -aryl, C 6 -C 18 -aralkyl, X represents, inter alia, H, C 1 -C 18 -alkyl, C 6 -C 18 -aryl, and/or Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, and wherein A represents OH, NH 2 , NHR, NR 2 , or O—CO—R 8 , and W represents a mineral acid, carboxylic acid, Lewis acid, or organic acid, wherein n is a whole or a fractional number from 0 to 4, and catalyst A represents 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. The use of said dialkylphosphonic acids, esters, and salts is also disclosed.

  本发明涉及一种生产单官能团二烷基膦酸、酯和盐的方法，其特征在于在催化剂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，然后将所述烷基膦酸、盐或酯（II）与含有C═C、C═O或C═N双键的化合物反应，得到类型为（III）的化合物，其中R1、R2、R3、R4、R5、R6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，X代表H、C1-C18-烷基、C6-C18-芳基和/或Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K、H，其中A代表OH、NH2、NHR、NR2或O—CO—R8，W代表矿酸、羧酸、路易斯酸或有机酸，n是从0到4的整数或分数，催化剂A代表过渡金属和/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个配体组成的催化剂体系。还公开了所述二烷基膦酸、酯和盐的用途。
• Asymmetric coupling of arylmagnesium bromides with allylic esters
  作者：Tamejiro Hiyama、Noriko Wakasa

  DOI：10.1016/s0040-4039(00)98166-8

  日期：1985.1
• VERFAHREN ZUR HERSTELLUNG VON MONO-CARBOXYFUNKTIONALISIERTEN DIALKYLPHOSPHINSÄUREN, -ESTERN UND -SALZEN MITTELS VINYLESTER EINER CARBONSÄURE UND IHRE VERWENDUNG
  申请人：Clariant Finance (BVI) Limited

  公开号：EP2373667B1

  公开（公告）日：2013-12-11
• US8735476B2
  申请人：——

  公开号：US8735476B2

  公开（公告）日：2014-05-27