(R)-2-(diethoxyphosphoryl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl | 132532-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(diethoxyphosphoryl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl
• 英文别名: (R)-2'-(diethoxyphosphoryl)-1,1'-binaphth-2-yl trifluoromethanesulfonate；[1-(2-diethoxyphosphorylnaphthalen-1-yl)naphthalen-2-yl] trifluoromethanesulfonate
• CAS: 132532-05-9
• 化学式: C₂₅H₂₂F₃O₆PS
• 分子量: 538.481
• InChiKey: JRMSDVSWFWINLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(diethoxyphosphoryl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 12.0h， 以89%的产率得到(R)-diethyl [2′-hydroxy-(1,1′-binaphthalen)-2-yl]phosphonate
  参考文献：
  名称：

  A New BINOL-Derived Chiral Bifunctional Phosphine Organocatalyst: Preparation and Application in Asymmetric (Aza)-Morita-Baylis-Hillman Reactions

  摘要：

  A new BINOL-derived chiral bifunctional phosphine has been designed and successfully prepared, which features a cyclic substructure of 1,3,5-diazaphosphinane. This chiral phosphine possesses good air stability in solid state, and it can be conveniently used as a relatively more nucleophilic phosphine organocatalyst. Preliminary investigations showed that it could generally afford fair to excellent yields but only modest enantioselectivity in the (aza)-Morita-Baylis-Hillman reactions of activated olefins such as ethyl acrylate and methyl vinyl ketone with aldehydes or imines. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus Sulfer and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]

  DOI：

  10.1080/10426507.2012.761987
• 作为产物：
  描述：

  (R)-1,1'-Bi-2-naphthol 在 吡啶 、 sodium formate 、 palladium diacetate 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 二甲基亚砜 为溶剂， 生成 (R)-2-(diethoxyphosphoryl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl
  参考文献：
  名称：

  手性双功能膦-羧酸盐配体，用于钯（0）催化的对映选择性CH芳基化

  摘要：

  先前的对映选择性Pd 0催化的CH活化反应是通过手性辅助配体，手性碱或它们的双分子混合物通过一致的金属化-去质子化机理进行的。这项研究描述了基于双萘基支架的新手性双功能配体的开发，该萘并膦既包含膦又包含羧酸部分。最佳配体为解对称的C（sp 2）-H芳基化反应提供了高收率和对映选择性，从而导致5,6-二氢菲啶，而相应的单官能配体显示出低对映选择性。事实证明，该双功能体系适用于一系列取代的二氢菲啶，并允许消旋底物的平行动力学拆分。

  DOI：

  10.1002/anie.201712061

文献信息

• Heterodimerization of Olefins. 1. Hydrovinylation Reactions of Olefins That Are Amenable to Asymmetric Catalysis
  作者：T. V. RajanBabu、Nobuyoshi Nomura、Jian Jin、Malay Nandi、Haengsoon Park、Xiufeng Sun

  DOI：10.1021/jo035171b

  日期：2003.10.1

  counteranion (BARF or SbF6) in an enantioselective version of the Ni-catalyzed reaction raises the prospects of developing a practical route for the synthesis of 3-arylbutenes. Several pharmaceutically relevant compounds, including widely used 2-arylpropionic acids, can be synthesized from these key intermediates. This reaction appears to be quite general. Synthesis of several new 2-diphenylphosphino-1

  通过对配体和抗衡离子作用的系统检查，发现了用于乙烯和各种功能化乙烯基芳烃的近定量和高度选择性共聚的新方案。在典型的反应中，在-56℃下，在[CH2Cl2]中，在[CH3Cl2]中分别存在0.0035当量的[（烯丙基）NiBr] 2，三苯膦和AgOTf，4-溴苯乙烯和乙烯进行共二聚，得到3-（4-溴苯基）-1 -丁烯的收率和选择性均> 98％。与[（烯丙基）PdX] 2的相应反应效率低下且选择性低，在鉴定出可行的系统之前可能需要进一步优化。产生可比的产率和选择性的另一有用方案涉及使用由2-二苯基膦基苯甲酸烯丙酯，Ni（COD）2和（C 6 F 5）3 B制备的单组分催化剂。识别手性半不稳定配体（例如，（R）-2-甲氧基-2'-二苯基膦基-1,1'-联萘基，MOP）与高度离解的抗衡阴离子（BARF或SbF6）之间的协同关系Ni催化的反应的发展提出了开发合成3-芳基丁烯的实用路线的前景。可以从这
• Chiral Carboxylic Acid Enabled Achiral Rhodium(III)‐Catalyzed Enantioselective C−H Functionalization
  作者：Luqing Lin、Seiya Fukagawa、Daichi Sekine、Eiki Tomita、Tatsuhiko Yoshino、Shigeki Matsunaga

  DOI：10.1002/anie.201807610

  日期：2018.9.10

  CpxRhIII/chiral carboxylic acid catalyzed asymmetric C−H alkylation of diarylmethanamines with a diazomalonate, followed by cyclization and decarboxylation to afford 1,4‐dihydroisoquinolin‐3(2H)‐one. Secondary alkylamines as well as nonprotected primary alkylamines underwent the transformation with high enantioselectivities (up to 98.5:1.5 e.r.) by using a newly developed chiral carboxylic acid as the sole source

  报告的是非手性Cp x Rh III /手性羧酸与重氮丙二酸酯催化的二芳基甲胺的不对称CH烷基化反应，然后环化和脱羧得到1,4-二氢异喹啉-3（2H）-一。通过使用新开发的手性羧酸作为唯一的手性来源，通过一致的金属化-去质子化机理实现对映选择性CH裂解，仲烷基胺和未保护的伯烷基胺都经历了高对映选择性（高达98.5：1.5 er）的转化。
• Stereospecific functionalization of (R)-(−)-1,1′-bi-2-naphthol triflate
  作者：Lilia Kurz、Gary Lee、David Morgans、Michael Joe Waldyke、Timothy Ward

  DOI：10.1016/s0040-4039(00)97053-9

  日期：1990.1
• Electrophilic Trifluoromethylation of Primary Phosphines: Synthesis of a <i>P</i>-Bis(trifluoromethyl) Derivative of BINAP
  作者：Nicolas Armanino、Raffael Koller、Antonio Togni

  DOI：10.1021/om100015s

  日期：2010.4.12

  The new chiral diphosphine ligand (R)-(2'-(bis(trifluoromethypphosphino)-1,1'-binaphthy-1-2yl)diphenylphosphine (2), which contains a bis(trilluoromethyl)phosphine group, was prepared in five steps from (R)-BINOL (5). As a key transformation, the unprecedented electrophilic double trifluoromethylation of the primary phosphine 8 was achieved using the hypervalent iodine trifluoromethylation reagent 1-trifluoromethyl-1,2-benziodoxo1-3-(1H)-one (1), derived from o-iodobenzoic acid. The palladium dichloride complex of this ligand (10) shows the P(CF(3))(2) group with a high degree of pyramidalization at the P atom and a relatively short Pd-P bond (2.2230(4) angstrom), both features being indicative of the strong s-character of the phosphorus lone pair.
• KURZ, LILIA;LEE, GARY;MORGANS, DAVID (JR);WALDYKE, MICHAEL JOE;WARD, TIMO+, TETRAHEDRON LETT., 31,(1990) N4, C. 6321-6324
  作者：KURZ, LILIA、LEE, GARY、MORGANS, DAVID (JR)、WALDYKE, MICHAEL JOE、WARD, TIMO+

  DOI：——

  日期：——