(2R)-propane-1,2-diyldibenzene | 19643-70-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R)-propane-1,2-diyldibenzene
• 英文别名: (R)-propane-1,2-diyldibenzene；(R)-(-)-1,2-diphenylpropane；propane-1,2-diyldibenzene；(-)-1,2-diphenylpropane；(R)-1,2-diphenylpropane；1,2-diphenyl-propane；[(2R)-1-phenylpropan-2-yl]benzene
• CAS: 19643-70-0
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: XLWCIHPMASUXPI-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2R)-propane-1,2-diyldibenzene 、 三氯化铁 生成 1,1-二苯基丙烷
  参考文献：
  名称：

  MASUDA, SHINJI;NAKAJIMA, TADASHI;SUGA, SOHEI, BULL. CHEM. SOC. JAP., 1983, 56, N 4, 1089-1094

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯乙烯 在 C₄₂H₆₃IrO₃PS⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以92%的产率得到
  参考文献：
  名称：

  Iridium-Catalyzed Asymmetric Hydrogenation with Simple Cyclohexane-Based P/S Ligands: In Situ HP-NMR and DFT Calculations for the Characterization of Reaction Intermediates

  摘要：

  We report a reduced but structurally valuable phosphite/phosphinite-thioether ligand library for the Ir-hydrogenation of 40 minimally functionalized alkenes, including relevant examples with poorly coordinative groups. We found that enantiomeric excesses are mainly dependent on the substrate structure and on some ligand parameters (i.e., the type of thioether/phosphorus moieties and the configuration of the phosphite group), whereas the substituents of the biaryl phosphite moiety had little impact. By tuning the ligand parameters we were able to find highly selective catalysts for a range of substrates (ee's up to 99%). These phosphite/phosphinite-thioether ligands have a simple backbone and thus yield simple NMR spectra that reduce signal overlap and facilitate the identification of relevant intermediates. Therefore, by combining HP-NMR spectroscopy and theoretical studies, we were also able to identify the catalytically competent Ir-dihydride alkene species, which made it possible to explain the enantioselectivity obtained.

  DOI：

  10.1021/acs.organomet.5b00790

文献信息

• Chiral Bis(N-sulfonylamino)phosphine- and TADDOL-Phosphite-Oxazoline Ligands: Synthesis and Application in Asymmetric Catalysis
  作者：Robert Hilgraf、Andreas Pfaltz

  DOI：10.1002/adsc.200404168

  日期：2005.1

  has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts

  制备了一系列N，P-配体，其包含手性恶唑啉环和嵌入在二氮磷吡啶环中的双（N-磺酰基氨基）膦基或衍生自TADDOL的环状亚磷酸酯基作为第二手性单元。这些模块化配体易于从手性氨基醇和手性1,2-二胺或TADDOLs合成。发现衍生自这些配体的钯和铱配合物分别是对映选择性烯丙基烷基化和烯烃氢化的有效催化剂。
• Catalytic asymmetric hydrogenation using a [2.2]paracyclophane based chiral 1,2,3-triazol-5-ylidene–Pd complex under ambient conditions and 1 atmosphere of H₂
  作者：Ayan Dasgupta、Venkatachalam Ramkumar、Sethuraman Sankararaman

  DOI：10.1039/c5ra03021h

  日期：——

  Chiral 1,2,3-triazol-5-ylidene–Pd complexes with the planar chiral [2.2]paracyclophane wing tip group have been synthesized and structurally characterized. The complex with a labile acetonitrile co-ligand is an excellent catalyst for chemoselective hydrogenation of alkynes and alkenes and enantioselective hydrogenation of prochiral alkenes at ambient conditions and 1.0 atmosphere of H2.

  具有平面手性[2.2]对环环糊精翼尖基团的手性1,2,3-三唑-5-亚烷基-Pd配合物已经合成并在结构上进行了表征。具有不稳定的乙腈共配体的配合物是在环境条件和1.0大气压的H 2下炔烃和烯烃的化学选择性加氢和前手性烯烃的对映选择性加氢的极佳催化剂。
• Enantioselective synthesis of tunable chiral pyridine–aminophosphine ligands and their applications in asymmetric hydrogenation
  作者：Youran Liu、Fei Chen、Yan-Mei He、Chenghao Li、Qing-Hua Fan

  DOI：10.1039/c9ob00770a

  日期：——

  ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral

  基于手性2-（吡啶-2-基）-取代的1,2,3,4-四氢喹啉骨架，对映选择性地合成了一个可调谐的手性吡啶-氨基膦配体的小型文库，该文库以高收率和优异的对映选择性通过钌催化的2-（吡啶-2-基）喹啉不对称氢化。该方案具有广泛的底物范围和温和的反应条件，可实现可扩展的合成。这些手性P，N配体已成功应用于Ir催化的基准烯烃和具有挑战性的七元环亚胺（包括苯并ze庚因和苯并二氮杂卓）的不对称加氢反应。在2,4-二芳基-3 H-苯并[ b ]氮杂和2,4-不对称氢化反应中，具有出色的对映和非对映选择性（高达99％ee和> 20：1 dr）和/或前所未有的化学选择性。二芳基-3 H-苯并[ b ] [1,4]二氮杂pine。
• New monoterpene-derived phosphinopyridine ligands and their application in the enantioselective iridium-catalyzed hydrogenation
  作者：Giorgio Chelucci、Mauro Marchetti、Andrei V. Malkov、Frédéric Friscourt、Martin E. Swarbrick、Pavel Kočovský

  DOI：10.1016/j.tet.2011.05.075

  日期：2011.7

  derivatives with a phosphine or phosphinite pendant (1–11) have been synthesized from (+)-α-pinene, (−)-isopinocampheol, and/or (+)-camphor via Kröhnke annulation or another annulation method as the key step for the construction of the pyridine nucleus. The iridium complex of 6 proved to catalyze hydrogenation of the prochiral unfunctionalized alkene 44 with 94% ee, whereas the complex of 2 was most efficient

  与膦或亚膦酸酯侧链（吡啶衍生物1 - 11）已经从（+）合成- α蒎烯，（ - ） -异松蒎醇，和/或（+） -经由Kröhnke环或另一个环的方法的关键步骤樟脑用于构建吡啶核。铱的6络合物被证明可以催化94％ee的前手性未官能化烯烃44的氢化，而2的络合物在肉桂基酯45（ee的83％）的氢化中效率最高。
• Iridium Catalysts with Chiral Bicyclic Pyridine-Phosphane Ligands for the Asymmetric Hydrogenation of Olefins
  作者：Xu Quan、Vijay Singh Parihar、Milan Bera、Pher G. Andersson

  DOI：10.1002/ejoc.201301141

  日期：2014.1

  New bicyclic pyridine-phosphane ligands were prepared, and their iridium complexes were evaluated in asymmetric hydrogenation of trisubstituted olefins with non-coordinating and weakly coordinating ...

  制备了新型双环吡啶-磷烷配体，并评价了它们的铱配合物在非配位和弱配位三取代烯烃的不对称加氢反应中...