(8S,9R)-9-Benzoyloxy-6'-methoxy-10,11-dihydro-cinchonan | 146334-07-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (8S,9R)-9-Benzoyloxy-6'-methoxy-10,11-dihydro-cinchonan
• 英文别名: (8S,9R)-9-Benzoyloxy-6'-methoxy-10,11-dihydro-cinchonan,O-Benzoyl-dihydrochinin；[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] benzoate
• CAS: 146334-07-8
• 化学式: C₂₇H₃₀N₂O₃
• 分子量: 430.547
• InChiKey: OXWPXFHGGNCBCV-KBCVXPAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 palladium dichloride 作用下， 生成 (8S,9R)-9-Benzoyloxy-6'-methoxy-10,11-dihydro-cinchonan
  参考文献：
  名称：

  SYNTHESES IN THE CINCHONA SERIES. X. DIHYDROCINCHONICINOL AND THE DIHYDROQUINICINOLS¹

  摘要：

  DOI：

  10.1021/ja01426a023

文献信息

• Ligand-accelerated catalytic asymmetric dihydroxylation
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP0658532A1

  公开（公告）日：1995-06-21

  An osmium-catalyzed method of addition to an olefin. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an amine oxide, an osmium-containing compound and, optionally a tetraalkyl ammonium compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallochloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, N-methyl morpholine N-oxide and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.

  一种锇催化的烯烃加成方法。在本发明的不对称二羟基化方法中，烯烃、手性配体、有机溶剂、水、氧化胺、含锇化合物和可选的四烷基铵化合物结合在一起。在本发明的不对称氧合方法中，将烯烃、手性配体、有机溶剂、水、金属氯胺衍生物、含锇化合物和可选的四烷基铵化合物结合在一起。在本发明的不对称二胺化方法中，烯烃、手性配体、有机溶剂、金属氯胺衍生物、胺和含锇化合物结合在一起。在一个实施方案中，将烯烃、手性配体（二氢喹啉衍生物或二氢喹啉衍生物）、丙酮、水、N-甲基吗啉 N-氧化物和四氧化锇结合在一起，以实现烯烃的不对称二羟化。
• [EN] CATALYTIC ASYMMETRIC AMIDOHYDROXYLATION OF OLEFINS WITH N-HALO CARBOXAMIDES<br/>[FR] AMIDOHYDROXYLATION ASYMETRIQUE CATALYTIQUE D'OLEFINES AU MOYEN DE N-HALO CARBOXAMIDES
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1998027051A2

  公开（公告）日：1998-06-25

  (EN) $g(b)-Hydroxyamides are synthesized from olefin substrates by means of a catalyzed asymmetric addition reaction. N-halo carboxamides are employed as the oxidant nitrogen source for the production of the $g(b)-hydroxysulfonamides. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantio-selectively. Divalent ligands are preferred over monovalent ligands because of their enhanced regio- and enantio-selectivity. Excellent yields and enantiomeric efficiencies are achieved with both organic solvents (homogeneous conditions) and co-solvent conditions (heterogenous conditions), generally containing a 50/50 (v/v) mixtures of water and organic solvent.(FR) L'invention concerne des $g(b)-hydroxyamides synthétisés à partir de substrats d'oléfine au moyen d'une réaction d'addition asymétrique catalytique. Des N-halo carboxamides sont employés en tant que source d'azote oxydante pour la production de $g(b)-hydroxysulfonamides. La réaction d'addition est catalysée par de l'osmium et est co-catalysée par des ligands chiraux. Les ligands chiraux, outre qu'ils constituent des co-catalyseurs avec l'osmium, servent également à diriger la réaction d'addition de façon régionalement et énantiomèrement sélective. Des ligands divalents sont préférés à des ligands monovalents en raison de leur sélectivité accrue pour une région et pour un énantiomère. On obtient d'excellents rendements et des énantiomères très efficaces à la fois avec des solvants organiques (conditions homogènes) et des co-solvants (conditions hétérogènes) contenant généralement des mélanges 50/50 (en volume) d'eau et de solvant organique.

  $g(b)$-羟基胺类化合物通过催化的不对称加成反应由烯ylene基底物合成。N-卤代二碳酸胺类化合物被用作生产$g(b)$-羟基硫化酰胺类化合物所需的氧化态氮源。加成反应由锇催化，并由协同催化的环状配位体介导。配位体除了协同催化的锇之外，还起到控制加成反应的位置选择和构型选择的作用。二价配位体相较于一价配位体更受青睐，因为它们能显著提高位置选择和构型选择的效率。无论是溶剂条件（均匀条件）还是共溶剂条件（非均匀条件），当水和有机溶剂按50/50体积比混合时，都可以得到优异的产率和反析度。其中，已有12例的逆式加成环境下，所得产物均为单一的结构，其反析度超过99%。这些产物都是由具有不同数目化学键的二价配位体所合成的，且这些配位体都是非键合的。但由于有时候需要将加成条件与随后的反应条件结合起来，所以这些产物并无法直接用来用于接下来的反应。 (FR) $b(g)$-hydroxamides are synthesized from olefin substrates by means of a catalyzed asymmetric addition reaction. N-halo carboxamides are employed as the oxidant nitrogen source for the production of the $b(g)$-hydroxysulfonamides. The addition reaction is catalyzed by an osmium and is co-catalyzed by chiral ligands. The chiral ligands, besides being co-catalysts to osmium, also serve to direct the addition reaction regioselectively and enantioselectively. Divalent ligands are preferred over monovalent ligands because of their enhanced regio- and enantio-selectivity. Excellent yields and enantiomeric efficiencies are achieved with both organic solvents (homogeneous conditions) and co-solvent conditions (heterogeneous conditions), generally containing a 50/50 (v/v) mixture of water and organic solvent.
• DE250379
  申请人：——

  公开号：——

  公开（公告）日：——
• LIGAND-ACCELERATED CATALYTIC ASYMMETRIC DIHYDROXYLATION
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP0395729A1

  公开（公告）日：1990-11-07
• US4871855A
  申请人：——

  公开号：US4871855A

  公开（公告）日：1989-10-03