3,8,8-triphenyl-2-oxa-3-aza-bicyclo[2.2.2]octan-6-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,8,8-triphenyl-2-oxa-3-aza-bicyclo[2.2.2]octan-6-one
• 英文别名: (+)-3,8,8-triphenyl-2-oxa-3-aza-bicyclo[2.2.2]octan-6-one；3,8,8-Triphenyl-2-oxa-3-azabicyclo[2.2.2]octan-6-one
• 化学式: C₂₄H₂₁NO₂
• 分子量: 355.436
• InChiKey: UCXHEHZJJRUZAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4-二苯基-2-环己烯-1-酮 、 亚硝基苯 在 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以56%的产率得到3,8,8-triphenyl-2-oxa-3-aza-bicyclo[2.2.2]octan-6-one
  参考文献：
  名称：

  Enantioselective Tandem O-Nitroso Aldol/Michael Reaction

  摘要：

  This communication presents studies that illustrated nitroso Diels-Alder adduct has been obtained in uniformly high enantioselectivity via a tandem nitroso aldol/Michael reaction using an amine catalyst. The regiochemical outcome of this construction is documented to be the opposite to that of the normal nitroso aldol reaction, which has been determined by X-ray analysis. The reaction of the enone with silver-BINAP catalyst has also been investigated in conjunction with the control of regiochemistry in a stepwise process.

  DOI：

  10.1021/ja049741g

文献信息

• Process of making alpha-aminooxyketone/alpha-aminooxyaldehyde and alpha-hydroxyketone/alpha-hydroxyaldehyde compounds and a process making reaction products from cyclic alpha,beta-unsaturated ketone substrates and nitroso substrates
  申请人：Momiyama Norie

  公开号：US20070037973A1

  公开（公告）日：2007-02-15

  The present invention is directed to a process of making α-aminooxyketone and α-hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X a —X c represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound. The present invention results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction. The substrates of this reaction are generally cyclic α,β-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic α,β-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

  本发明涉及一种制备α-氨氧基酮和α-羟基酮化合物的方法。合成途径通常涉及在催化剂存在下反应醛或酮底物和亚硝基底物，所述催化剂的公式为（IV）：其中Xa-Xc分别独立表示氮、碳、氧或硫，Z表示具有或不具有取代基的4到10个成员环，并可选择进一步步骤将形成的α-氨氧基酮化合物转化为α-羟基酮化合物。本发明的结果是具有高对映选择性和高纯度的α-氨氧基酮和α-羟基酮化合物。本发明还涉及一种催化不对称O-亚硝基Aldol/Michael反应。该反应的底物通常为环状α,β-不饱和酮底物和亚硝基底物。该方法通常涉及在脯氨酸基催化剂存在下反应环状α,β-不饱和酮底物和亚硝基底物，以提供杂环产物。
• PROCESS OF MAKING ALPHA-AMINOOXYKETONE/ALPHA-AMINOOXYALDEHYDE AND ALPHA-HYDROXYKETONE/ALPHA-HYDROXYALDEHYDE COMPOUNDS AND A PROCESS MAKING REACTION PRODUCTS FROM CYCLIC ALPHA, BETA-UNSATURATED KETONE SUBSTRATES AND NITROSO SUBSTRATES
  申请人：Momiyama Norie

  公开号：US20100099915A1

  公开（公告）日：2010-04-22

  The present invention is directed to a process of making α-aminooxyketone and α-hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X a —X c represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound. The present invention results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction. The substrates of this reaction are generally cyclic α,β-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic α,β-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

  本发明涉及一种制备α-氨氧酮和α-羟基酮化合物的过程。合成路径通常涉及在催化剂的存在下反应醛或酮底物和亚硝基底物，催化剂的公式为（IV）：其中Xa-Xc代表独立的氮、碳、氧或硫，Z代表具有或不具有取代基的4到10个成员环，并可选择进一步步骤将形成的α-氨氧酮化合物转化为α-羟基酮化合物。本发明产生了具有高对映选择性和高纯度的α-氨氧酮和α-羟基酮化合物。本发明还涉及一种催化不对称O-亚硝基Aldol/Michael反应。该反应的底物通常是环状α，β-不饱和酮底物和亚硝基底物。该方法通常涉及在脯氨酸基催化剂的存在下反应环状α，β-不饱和酮底物和亚硝基底物，以提供杂环产物。
• US7872123B2
  申请人：——

  公开号：US7872123B2

  公开（公告）日：2011-01-18
• US8252941B2
  申请人：——

  公开号：US8252941B2

  公开（公告）日：2012-08-28
• US8372985B2
  申请人：——

  公开号：US8372985B2

  公开（公告）日：2013-02-12