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13-[1-[2-[(12,14-Dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)oxy]naphthalen-1-yl]naphthalen-2-yl]oxy-12,14-dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene | 1430069-09-2

中文名称
——
中文别名
——
英文名称
13-[1-[2-[(12,14-Dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)oxy]naphthalen-1-yl]naphthalen-2-yl]oxy-12,14-dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
英文别名
13-[1-[2-[(12,14-dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)oxy]naphthalen-1-yl]naphthalen-2-yl]oxy-12,14-dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
13-[1-[2-[(12,14-Dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)oxy]naphthalen-1-yl]naphthalen-2-yl]oxy-12,14-dimethyl-12,14-diaza-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene化学式
CAS
1430069-09-2;1430069-10-5;1430069-11-6
化学式
C64H48N4O2P2
mdl
——
分子量
967.058
InChiKey
BALHQIAHCWKSEB-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    18.3
  • 重原子数:
    72
  • 可旋转键数:
    5
  • 环数:
    14.0
  • sp3杂化的碳原子比例:
    0.06
  • 拓扑面积:
    38.2
  • 氢给体数:
    0
  • 氢受体数:
    2

反应信息

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文献信息

  • Metal Complexes Containing Enantiopure Bis(diamidophosphite) Ligands in Asymmetric Allylic Substitution and Hydroformylation Reactions
    作者:Maritza J. Bravo、Rosa M. Ceder、Arnald Grabulosa、Guillermo Muller、Mercè Rocamora、J. Carles Bayón、Daniel Peral
    DOI:10.1021/acs.organomet.5b00457
    日期:2015.8.10
    Enantiopure bis(diamidophosphite) ligands with a heterocyclic terminal fragment derived from (R)- and (S)-N,N'-dimethyl-1,1'-binaphthyldiamine and bridging fragments derived from (S,S)-2,3-butanediol (a), (4R,5R)-4,5-di(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (b), and (R)-and (S)-1,1'-bi-2-naphthol (c) were used to prepare the palladium complexes with general formula [Pd(eta(3)-2-CH3-C3H4)(P-P)][X] (X = PF6, 1a-(S;S-al;S-al;S), 113-(R;R-al;R-al;R), 1b-(S;R-al;R-al;S), 1c-(R;R-al;R), 1c-(R;S-al;R); X = BPh4, 2a-(R;S-al;S-al;R), 2c-(R;R-al;R)), which have been fully characterized. The solid-state structure for complexes 1a-(S;S-al;S-al;S) and 1b-(R;R-al;R-al;R) has been determined by X-ray diffraction. The catalytic performance of the palladium complexes has been evaluated in asymmetric allylic alkylation and amination reactions with the benchmark substrate. The influence of the nature and absolute configuration of both the terminal and bridging fragments of the bis(diamidophosphite) ligands on the asymmetric induction is discussed. The best results in terms of enantioselectivity were obtained with 1c-(R;R-al;R), affording enantiomeric excesses up to 85% in both alkylation and amination reactions. A large match-mismatch effect between the absolute configurations of stereocenters of ligand c has been observed in the allylic amination process. Preliminary results in the rhodiumcatalyzed asymmetric hydroformylation of styrene by using bis(diamidophosphite) ligands a, b, and c disclosed in all cases low enantiomeric discrimination for the branched aldehyde. Both for the allylic alkylation and for the hydroformylation reaction, a related monodentate diamidophosphite d, derived from (R)-N,N'-dimethyl-1,1'-binaphthyldiamine and (S)-borneol, was also tested. Palladium complexes of this monodentate ligand showed fairly good enantioselectivity in allylic alkylation, but with very low rate, while the rhodium complex of d rendered better enantioselectivity (37% ee) than the bidentate ligands a-c in the hydroformylation of styrene.
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