(S)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1,1'-binaphthyl | 820978-68-5

• 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: (S)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1,1'-binaphthyl
• 英文别名: bis[3,5-bis(trifluoromethyl)phenyl]-(1-naphthalen-1-ylnaphthalen-2-yl)phosphane
• CAS: 820978-68-5
• 化学式: C₃₆H₁₉F₁₂P
• 分子量: 710.501
• InChiKey: UNPBXQROYYRJOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  49
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  magnesium,1,3-bis(trifluoromethyl)benzene-5-ide,bromide 在 盐酸 、 三氯硅烷 、 碘 、 氧气 、 magnesium 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 23.0h， 生成 (S)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1,1'-binaphthyl
  参考文献：
  名称：

  使用三苯膦或亚磷酸三乙酯作为氧受体，使膦氧化物的立体特异性脱氧并保持构型。

  摘要：

  [反应：见正文]描述了一种新的方案，用于在保持构型的情况下对各种氧化膦进行脱氧。新方法的优点包括条件更温和，反应时间大大缩短。还介绍了有关起始氧化膦与牺牲性三苯膦之间氧转移的机理的研究。

  DOI：

  10.1021/ol048227c
• 作为试剂：
  描述：

  4-甲氧基苯乙烯 在 (S)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1,1'-binaphthyl 三氯硅烷 作用下， 生成 (S)-1-(4-methoxyphenyl)-1-(trichlorosilyl)ethane
  参考文献：
  名称：

  Modification of Chiral Monodentate Phosphine (MOP) Ligands for Palladium-Catalyzed Asymmetric Hydrosilylation of Styrenes

  摘要：

  在钯催化的苯乙烯与三氯硅烷的不对称氢化硅烷化反应中，研究了几种手性单膦配体 (R)-2-二芳基膦基-1,1'-联萘 (2) 的对映选择性。在与 (R)-2-双[3,5-双(三氟甲基)苯基]膦基-1,1'-联萘 (2g) 的反应中观察到最高的对映选择性，得到 98 的 (S)-1-苯基乙醇氢化硅烷化产物氧化后的％ee。

  DOI：

  10.1246/cl.2000.1272

文献信息

• Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki–Miyaura Cross-coupling
  作者：Wangqin Ji、Hai-Hong Wu、Junliang Zhang

  DOI：10.1021/acscatal.9b04354

  日期：2020.1.17

  palladium/WJ-Phos-catalyzed Suzuki–Miyaura coupling reaction for efficient construction of axially chiral biaryl monophosphine oxides was developed. A series of axially chiral biaryl monophosphine oxides were obtained in good yields and with high enantioselectivities. The practicability of this reaction was validated in the straightforward synthesis of axially chiral biaryl monophosphine ligand and demonstrated

  开发了一种高对映选择性的钯/ WJ-Phos催化的Suzuki-Miyaura偶联反应，可有效构建轴向手性联芳基单膦氧化物。以高收率和高对映选择性获得了一系列轴向手性联芳基单膦氧化物。该反应的实用性在轴向手性联芳基单膦配体的直接合成中得到验证，并通过100 g规模的合成得到证明。此外，产物的各种官能化使其成为合成其他手性联芳基膦的平台分子。
• Optically active tertiary phosphine compounds, transition metal complexes comprising the same as ligands and process for preparing optically active organic silicon compounds using said transition metal complexes
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0731105A1

  公开（公告）日：1996-09-11

  A tertiary phosphine compound of the formula (1): in which R1 and R1' are hydrogen atoms or together form -CH=CH-CH=CH-; R2 and R3 together form a group of the formula (a): in which represent a bond to be bonded to the R3 group, and represents a bond to be bonded to the R2 group when R1 and R1' together form -CH=CH-CH=CH-, or when R1 is a hydrogen atom, R2 and R3 together form -CH=CH-CH=CH- or R2 is a hydrogen atom and R3 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group; A1 is a 3-trifluoromethylphenyl group or a 3,5-bis(trifluoromethyl)phenyl group when R1 is a hydrogen atom and R2 and R3 together form -CH=CH-CH=CH-, or a substituted or unsubstituted phenyl group when R1 is not a hydrogen atom or when R2 and R3 do not together form -CH=CH-CH=CH-.

  一种式（1）的叔膦化合物： 其中 R1 和 R1'为氢原子或共同形成-CH=CH-CH=CH-； R2 和 R3 共同形成式（a）的基团： 其中，当 R1 和 R1'共同形成-CH=CH-CH=CH-，或当 R1 是氢原子，R2 和 R3 共同形成-CH=CH-CH=CH-，或 R2 是氢原子，R3 是取代或未取代的烷基，或取代或未取代的苯基时，代表与 R3 基团键合的键，代表与 R2 基团键合的键；当 R1 是氢原子且 R2 和 R3 共同形成-CH=CH-CH=CH-时，A1 是 3-三氟甲基苯基或 3,5-双（三氟甲基）苯基；当 R1 不是氢原子或 R2 和 R3 不共同形成-CH=CH-CH=CH-时，A1 是取代或未取代的苯基。
• Asymmetric Hydrosilylation of Styrenes Catalyzed by Palladium−MOP Complexes:  Ligand Modification and Mechanistic Studies
  作者：Tamio Hayashi、Seiji Hirate、Kenji Kitayama、Hayato Tsuji、Akira Torii、Yasuhiro Uozumi

  DOI：10.1021/jo001614p

  日期：2001.2.1

  In the palladium-catalyzed asymmetric hydrosilylation of styrene (3a) with trichlorosilane, several chiral monophosphine ligands, (R)-2-diarylphosphino-1,1'-binaphthyls(2a-g), were examined for their enantioselectivity. The highest enantioselectivity was observed in the reaction with (R)-2-bis [3,5-bis(trifluoromethyl)phenyl] phosphino-l,1'-binaphthyl (2g), which gave (S)-1-phenylethanol (5a) of 98% ee after oxidation of the hydrosilylation product, 1-phenyl-1-(trichlorosilyl)ethane (4a). The palladium complex of 2g also efficiently catalyzed the asymmetric hydrosilylation of substituted styrenes on the phenyl ring or at the beta position to give the corresponding chiral benzylic alcohols of over 96% ee. Deuterium-labeling studies on the hydrosilylation of regiospecifically deuterated styrene revealed that P-hydrogen elimination from l-phenylethyl(silyl)palladium intermediate is very fast compared with reductive elimination giving hydrosilylation product when ligand 2g is used. The reaction of o-allylstyrene (9) with trichlorosilane catalyzed by (R)-2g/Pd gave (1S,2R)-1-methyl-2-(trichlorosilylmethyl)indan (10) (91% ee) and (S)-1-(2-(propenyl)phenyl)-1-trichlorosilylethanes (11a and 11b) (95% ee). On the basis of their opposite configurations at the benzylic position, a rationale for the high enantioselectivity of ligand 2g is proposed.
• METAL COMPLEXES FOR USE IN THE CARBONYLATION OF ETHYLENICALLY UNSATURATED COMPOUNDS
  申请人：Lucite International UK Limited

  公开号：EP2007703A1

  公开（公告）日：2008-12-31
• US5621129A
  申请人：——

  公开号：US5621129A

  公开（公告）日：1997-04-15