2-(N-phenylaminooxy)dodecanal | 1057091-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: 2-(N-phenylaminooxy)dodecanal
• 英文别名: 2-Anilinooxydodecanal
• CAS: 1057091-42-5
• 化学式: C₁₈H₂₉NO₂
• 分子量: 291.434
• InChiKey: UKRSZOUTRWYUSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-phenylaminooxy)dodecanal 、 硝基甲烷 在 C₃₆H₅₄N₂O₂^(4-)*Cu⁽²⁺⁾*2H⁽¹⁺⁾ 、 sodium hydroxide 、 copper(II) acetate monohydrate 作用下， 以 水 为溶剂， 反应 12.5h， 以70%的产率得到
  参考文献：
  名称：

  用于合成 1,2-二醇的有机催化不对称串联 α-氨基氧化-亨利反应：(-)-L-苏式-鞘氨醇的全合成

  摘要：

  描述了一种通过有机催化串联 α-氨基氧化-亨利反应合成 1,2-二醇衍生物抗和顺-β,γ-二羟基硝基烷烃的新型快速不对称合成方法。目标二醇衍生物以良好的产率合成，在温和条件下具有出色的对映选择性和低至中等的非对映选择性。抗肿瘤和抗银屑病药物 (-)-L-苏式-二氢鞘氨醇的合成证明了标题反应中生成的片段的合成效用。

  DOI：

  10.1002/ejoc.201701289
• 作为产物：
  描述：

  十二醛 、 亚硝基苯 在 D-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2-(N-phenylaminooxy)dodecanal
  参考文献：
  名称：

  用于合成 1,2-二醇的有机催化不对称串联 α-氨基氧化-亨利反应：(-)-L-苏式-鞘氨醇的全合成

  摘要：

  描述了一种通过有机催化串联 α-氨基氧化-亨利反应合成 1,2-二醇衍生物抗和顺-β,γ-二羟基硝基烷烃的新型快速不对称合成方法。目标二醇衍生物以良好的产率合成，在温和条件下具有出色的对映选择性和低至中等的非对映选择性。抗肿瘤和抗银屑病药物 (-)-L-苏式-二氢鞘氨醇的合成证明了标题反应中生成的片段的合成效用。

  DOI：

  10.1002/ejoc.201701289

文献信息

• Processes for production of alpha-aminooxyketones and alpha-hydroxyketones
  申请人：Saito Susumu

  公开号：US20070055081A1

  公开（公告）日：2007-03-08

  The present invention provides a method for easily obtaining α-aminooxyketone compound which is a synthetic equivalent for monosaccharide and pentoses, and a equivalent of α-hydroxyketone compound that can be synthetic intermediates of various physiologically active materials, in high yield; to pave the way for the synthesis of monosaccharide and furthermore of oligosaccharide from the resulting α-hydroxyketone compound induced from α-aminooxyketone compound; and to open new possibilities for the synthesis of various sugar medicines such as anticancer agents, antithrombogenic agents, anti-viral agents, anti-HIV agents, inhibitors of cholesterol synthesis, verotoxin neutralizing agents. According to the invention, a carbonyl compound is allowed to react with a nitroso compound to produce an α-aminooxyketone compound using a catalyst containing a heterocyclic compound shown in the general formula (I) (wherein X1, X2 and X3 independently represent nitrogen, carbon, oxygen or sulfur; and Z represents a substituted or unsubstituted 5- to 10-membered ring).

  本发明提供了一种方法，以高产率轻松获得α-氨氧酮化合物，该化合物是单糖和戊糖的合成等效物，以及α-羟基酮化合物的等效物，可用作各种生理活性物质的合成中间体，为从α-氨氧酮化合物诱导的α-羟基酮化合物合成单糖并进一步合成寡糖铺平道路，并为合成各种糖类药物如抗癌剂、抗凝血剂、抗病毒剂、抗HIV剂、胆固醇合成抑制剂、痢疾毒素中和剂开辟新的可能性。根据本发明，允许羰基化合物与亚硝基化合物反应，使用包含在一般式（I）中的杂环化合物的催化剂（其中X1、X2和X3独立地表示氮、碳、氧或硫；Z表示取代或未取代的5至10元环）。
• 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。
• PROCESSES FOR PRODUCTION OF ALPHA-AMINOOXYKETONES AND ALPHA-HYDROXYKETONES
  申请人：Japan Science and Technology Agency

  公开号：EP1717221A1

  公开（公告）日：2006-11-02

  The present invention is to provide a method for easily obtaining α-aminooxyketone compound which is a synthetic equivalent for monosaccharide and pentoses, and a equivalent of α-hydroxyketone compound that can be synthetic intermediates of various physiologically active materials, in high yield; to pave the way for the synthesis of monosaccharide and furthermore of oligosaccharide from the resulting α-hydroxyketone compound induced from α-aminooxyketone compound; and to open new possibilities for the synthesis of various sugar medicines such as anticancer agents, antithrombogenic agents, anti-HIV agents, inhibitors of cholesterol synthesis, verotoxin neutralizing agents. According to the invention, a carbonyl compound is allowed to react with a nitroso compound to produce an α-aminooxyketone compound using a catalyst containing a heterocyclic compound shown in the general formula (I) (wherein X1, X2 and X3 independently represent nitrogen, carbon, oxygen or sulfur; and Z represents a substituted or unsubstituted 5-to 10-membered ring).

  本发明的目的是提供一种方法，便于高产率地获得α-氨基氧酮化合物，它是单糖和戊糖的合成等价物，也是可作为各种生理活性物质合成中间体的α-羟基酮化合物的等价物；为从α-氨基酮化合物诱导出的α-羟基酮化合物合成单糖和寡糖铺平道路；为合成各种糖类药物，如抗癌剂、抗血栓形成剂、抗艾滋病毒剂、胆固醇合成抑制剂、verotoxin 中和剂等提供新的可能性。根据本发明，使用含有通式（I）所示杂环化合物（其中 X1、X2 和 X3 独立代表氮、碳、氧或硫；Z 代表取代或未取代的 5 至 10 元环）的催化剂，使羰基化合物与亚硝基化合物反应生成 α-氨基氧酮化合物。
• PROCESS OF MAKING ALFA-AMINOOXYKETONE/ ALFA-AMINOOXYALDEHYDE AND ALFA-HYDROXYKETONE/ ALFA-HYDROXYALDEHYDE COMPOUNDS AND A PROCESS OF MAKING REACTION PRODUCTS FROM CYCLIC ALFA, BETA-UNSATURATED KETONE SUBSTRATES AND NITROSO SUBSTRATES
  申请人：Japan Science and Technology Agency

  公开号：EP1742905A2

  公开（公告）日：2007-01-17