[1,1'-bi(cyclohexan)]-1-en-3-one | 7122-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1,1'-bi(cyclohexan)]-1-en-3-one
• 英文别名: 3-cyclohexylcyclohex-2-enone；3-cyclohexyl-cyclohex-2-enone；3-Cyclohexyl-cyclohex-2-enon；1-Cyclohexyl-cyclohexen-(1)-on-(3)；3-Cyclohexylcyclohex-2-en-1-one
• CAS: 7122-91-0
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: AVDLJPAYVGDVGS-UHFFFAOYSA-N

物化性质

• 沸点：
  93 °C(Press: 0.3 Torr)
• 密度：
  0.9994 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1,1'-bi(cyclohexan)]-1-en-3-one 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 3-(环己基)环己烯
  参考文献：
  名称：

  Laber, Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 79,83

  摘要：

  DOI：
• 作为产物：
  描述：

  1-环己基-2-甲基-环戊烯 在 sodium hydroxide 、 水 作用下， 生成 [1,1'-bi(cyclohexan)]-1-en-3-one
  参考文献：
  名称：

  Laber, Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 79,83

  摘要：

  DOI：

文献信息

• CATALYST FOR ASYMMETRIC HYDROGENATION AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CARBONYL COMPOUND USING THE SAME
  申请人：YAMADA Shinya

  公开号：US20120136176A1

  公开（公告）日：2012-05-31

  The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

  本发明提供了一种用于通过选择性不对称加氢α，β-不饱和羰基化合物制备光学活性羰基化合物的催化剂，该催化剂在反应混合物中不溶解，并提供了制备相应光学活性羰基化合物的方法。特别地，该发明提供了一种催化剂，通过选择性不对称加氢柠檬醛、香叶醛或柠檬醛制备出用作香料或芳香剂的光学活性香茅醛。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，包括：来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种金属负载物质，其中至少一种金属负载在一种载体上；一种光学活性肽化合物；和一种酸，还涉及使用该催化剂制备光学活性羰基化合物的方法。
• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones
  作者：Jeffrey C. Holder、Emmett D. Goodman、Kotaro Kikushima、Michele Gatti、Alexander N. Marziale、Brian M. Stoltz

  DOI：10.1016/j.tet.2014.11.048

  日期：2015.9

  The development and optimization of a palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enone conjugate acceptors is described. These reactions employ air-stable and readily-available reagents in an operationally simple and robust transformation that yields β-quaternary ketones in high yields and enantioselectivities. Notably, the reaction itself is highly tolerant of

  描述了钯催化芳基硼酸与环烯酮共轭受体的不对称共轭加成的开发和优化。这些反应采用空气稳定且易于获得的试剂，通过操作简单且稳健的转化，以高产率和对映选择性产生 β-季酮。值得注意的是，反应本身对大气中的氧气和湿气具有高度耐受性，因此不需要使用干燥或脱氧溶剂、特别纯化的试剂或惰性气氛。烯酮的环大小和β-取代基变化很大，可以合成多种β-季酮。最近，NH 4 PF 6的使用进一步扩大了底物范围，包括含杂原子的芳基硼酸和β-酰基烯酮底物。
• 1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP3 to trisubstituted enones. A new BF3 promoted cyclization reaction
  作者：Ming Chang P. Yeh、Paul Knochel、William M. Butler、Scott C. Berk

  DOI：10.1016/s0040-4039(00)82430-2

  日期：——

  The new copper reagents RCu(CN)Zn I · 2 BF31 containing various functional groups like esters, cyanides, chlorides or enoates react with β, β′- disubstituted enones to afford the Michael adducts 4–7 in high yields (81–98%). Cyano-substituted 1,4-adducts undergo a new cyclization reaction leading to the very stable bicyclic difluoroboron enolates 11a–11c which could be converted into the bicyclic diketones

  新型的铜试剂RCu（CN）Zn I·2 BF 3 1包含各种官能团，例如酯，氰化物，氯化物或烯酸酯，它们与β，β'-二取代的烯酮反应，以高收率提供了迈克尔加合物4-7（81- 98％）。氰基取代的1,4-加合物经历新的环化反应，从而生成非常稳定的双环二氟硼烯酸酯11a-11c，可以在温和的碱性条件下将其转化为双环二酮12。报告了11b的X射线结构。
• Enantioselective organocatalytic phospha-Michael reaction of α,β-unsaturated ketones
  作者：Shigang Wen、Pengfei Li、Haibo Wu、Feng Yu、Xinmiao Liang、Jinxing Ye

  DOI：10.1039/c0cc00094a

  日期：——

  Enantioselective organocatalytic phospha-Michael reaction of alpha,beta-unsaturated ketones and diaryl phosphine oxides has been developed for the first time employing multifunctional organocatalysts. Optically active products bearing quaternary chiral carbon stereocenters were obtained in high yields with good to excellent enantioselectivities (up to 98% ee).

  α，β-不饱和酮和二芳基氧化膦的对映选择性有机催化磷-迈克尔反应是首次使用多功能有机催化剂。以高收率获得具有良好至优异对映选择性（高达98％ee）的带有季手性碳立体中心的旋光产品。