ethyl (R,E)-2-(trifluoromethyl)-2-hydroxy-5-(4-chlorophenyl)-4-enoate

• 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: ethyl (R,E)-2-(trifluoromethyl)-2-hydroxy-5-(4-chlorophenyl)-4-enoate
• 英文别名: ethyl (2R,E)-2-(trifluoromethyl)-2-hydroxy-5-(4-chlorophenyl)pent-4-enoate；(R)-ethyl E-2-(trifluoromethyl)-2-hydroxy-5-(4-chlorophenyl)pent-4-enoate；ethyl (E,2R)-5-(4-chlorophenyl)-2-hydroxy-2-(trifluoromethyl)pent-4-enoate
• 化学式: C₁₄H₁₄ClF₃O₃
• 分子量: 322.712
• InChiKey: ZPJUWDHNCSDKLC-ITDFMYJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-烯丙基-4-氯苯 、 3,3,3-三氟丙酮酸乙酯 在 chiral PtCl₂ based NU-BIPHEP-type catalyst silver hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 ethyl (R,E)-2-(trifluoromethyl)-2-hydroxy-5-(4-chlorophenyl)-4-enoate
  参考文献：
  名称：

  铑催化的1，4-双（二苯基膦酰基）buta-1,3-diyne与束缚二炔的双[2 + 2 + 2]环加成反应：NU-BIPHEP双芳基二膦酸酯的模块化，高度通用的单罐合成。

  摘要：

  铑催化的1,4-双（二苯基膦酰基）丁1,3-二炔与束缚二炔的双[2 + 2 + 2]环加成反应为合成新型对位联芳基二膦提供了一种简单的单釜法，NU-BIPHEP。这种方法代表了对现有多步骤程序的重大改进。这些二膦的对映纯路易斯酸铂络合物是羰基-烯和Diels-Alder反应的高效催化剂，钌二膦二胺络合物催化酮的不对称还原，得到的ee可以与用BINAP对应的ee竞争。

  DOI：

  10.1021/ol702390p

文献信息

• [EN] BIARYL DIPHOSPHINES<br/>[FR] BIARYLDIPHOSPHINES
  申请人：UNIV NEWCASTLE

  公开号：WO2009044130A1

  公开（公告）日：2009-04-09

  A compound of formula (I):wherein: X is selected from O, S, NRN1, PRP1, SiRSi1RSi2, BRB1, CRC1RC2 and (CRC1RC2)2,, where RN1 is selected from H, C1-7 alkyl sulfonyl, benzyl and C1-7 alkyl, RP1 is selected from C1-7 alkyl and C5-7 aryl, RSi1 and RSi2 are independently selected from H, C1-7 alkyl, benzyl and C5-7 aryl, RB1 is selected from C1-7 alkyl, C5-7 aryl, C1-7 alkyloxy, C5-7 aryloxy, and RC1 and RC2 are independently selected from H, C1-7 alkyl, and C1-7 alkylester; if X is (CRC1RC2)2 then, the two carbon atoms may form part of a fused carbocyclic or heterocyclic ring, having between 3 and 7 ring atoms; R1 is selected from H, hydroxy, C1-7 alkyl, C1-7 alkyloxy, silyloxy, C1-7 alkylester; R2 is selected from H, hydroxy, C1-7 alkyl, C1-7 alkyloxy, silyloxy, C1-7 alkylester; and RP is selected from C5-20 aryl, di(C1-7 alkyl) amino, C1-7 alkoxy, chloro and C1-7 alkyl.

  式(I)的化合物：其中：X选自O、S、NRN1、PRP1、SiRSi1RSi2、BRB1、CRC1RC2和(CRC1RC2)2，其中RN1选自H、C1-7烷基磺酰基、苄基和C1-7烷基，RP1选自C1-7烷基和C5-7芳基，RSi1和RSi2分别选自H、C1-7烷基、苄基和C5-7芳基，RB1选自C1-7烷基、C5-7芳基、C1-7烷氧基、C5-7芳氧基，RC1和RC2分别选自H、C1-7烷基和C1-7烷酯基；如果X为(CRC1RC2)2，则两个碳原子可以构成具有3至7个环原子的融合环烷或杂环；R1选自H、羟基、C1-7烷基、C1-7烷氧基、硅烷氧基、C1-7烷酯基；R2选自H、羟基、C1-7烷基、C1-7烷氧基、硅烷氧基、C1-7烷酯基；RP选自C5-20芳基、二(C1-7烷基)氨基、C1-7烷氧基、氯和C1-7烷基。
• Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition of 1,4-Bis(diphenylphosphinoyl)buta-1,3-diyne with Tethered Diynes:  A Modular, Highly Versatile Single-Pot Synthesis of NU-BIPHEP Biaryl Diphosphines
  作者：Simon Doherty、Julian G. Knight、Catherine H. Smyth、Ross W. Harrington、William Clegg

  DOI：10.1021/ol702390p

  日期：2007.11.1

  procedure for the synthesis of a new class of tropos biaryl diphosphine, NU-BIPHEP. This methodology represents a significant improvement on existing multistep procedures. Enantiopure Lewis acid platinum complexes of these diphosphines are highly efficient catalysts for carbonyl-ene and Diels-Alder reactions, and ruthenium diphosphine-diamine complexes catalyze the asymmetric reduction of ketones to give

  铑催化的1,4-双（二苯基膦酰基）丁1,3-二炔与束缚二炔的双[2 + 2 + 2]环加成反应为合成新型对位联芳基二膦提供了一种简单的单釜法，NU-BIPHEP。这种方法代表了对现有多步骤程序的重大改进。这些二膦的对映纯路易斯酸铂络合物是羰基-烯和Diels-Alder反应的高效催化剂，钌二膦二胺络合物催化酮的不对称还原，得到的ee可以与用BINAP对应的ee竞争。
• Asymmetric carbonyl-ene and Friedel–Crafts reactions catalysed by Lewis acid platinum group metal complexes of the enantiopure atropisomeric biaryl-like diphosphine (S)-Me2-CATPHOS: a comparison with BINAP
  作者：Simon Doherty、Julian G. Knight、Hamid Mehdi-Zodeh

  DOI：10.1016/j.tetasy.2012.01.022

  日期：2012.2

  Lewis acid platinum and palladium complexes of (S)-Me-2-CATPHOS catalyse the carbonyl-ene reaction between allylbenzene derivatives and ethyl trifluoropyruvate to give the expected alpha-hydroxy esters with ee's up to 97%, while the corresponding reaction involving 2-allylfuran and thiophene was exclusively selective for Friedel-Crafts-type reactivity and gave the corresponding 2-hydroxy-trifluoromethyl ethyl esters in good yield and moderate to good enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.