2-Anilinooxy-4,4-dimethylcyclohexan-1-one | 888706-98-7

• 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-Anilinooxy-4,4-dimethylcyclohexan-1-one
• CAS: 888706-98-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: WKKAAHXQYBOJKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-Anilinooxy-4,4-dimethylcyclohexan-1-one 在 europioum(III) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 4,4-dimethyl-2-(phenylamino)cyclohex-2-enone 、 5,5-dimethyl-2-(phenylamino)cyclohex-2-enone
  参考文献：
  名称：

  Metal-Induced Reactions ofO-Nitroso Aldol Products

  摘要：

  路易斯酸催化剂在δ-氨基氧基酮（O-亚硝基醛醇产物）的转化过程中发挥着重要作用。本文介绍了金属离子促进 O-亚硝基醛醇产物的三种不同反应。

  DOI：

  10.1055/s-2006-933123
• 作为产物：
  描述：

  4,4-二甲基环己酮 在 trimethyltin methoxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 2-Anilinooxy-4,4-dimethylcyclohexan-1-one
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of α-Aminooxy and α-Hydroxy Ketone Using Nitrosobenzene

  摘要：

  The highly enantioselective and O-selective nitroso aldol reaction of tin enolates 2 and nitrosobenzene (1) has been developed with the use of (R)-BINAP-silver complexes as a catalyst. After the various silver salts were surveyed, the AgOTf and the AgClO4 complex were found to be optimal in the O-selective nitroso aldol reaction in both asymmetric induction (up to 97% ee) and regioselection (O/N = >99/1), affording aminooxy ketone 3. The product 3 can be transformed to alpha-hydroxy ketone 5 without any loss of enantioselectivity. Thus, the method provides an efficient approach to the catalytic enantioselective introduction of oxygen alpha- to the carbonyl group.

  DOI：

  10.1021/ja0298702

文献信息

• OPTICALLY ACTIVE ALPHA-AMINOOXYKETONE DERIVATIVES AND PROCESS FOR PRODUCTION THEREOF
  申请人：Tokyo University of Science

  公开号：EP1661885A1

  公开（公告）日：2006-05-31

  The corresponding α-aminooxy ketone is manufactured with a high yield and a high enantioselectivity. A manufacturing method for an optically active α-aminooxy ketone derivative expressed by formula (1), wherein a ketone expressed by formula (2) is caused to react with a nitroso compound expressed by formula (3) in the presence of a proline derivative expressed by formula (4). In the formula, R1 and R2 respectively denote an alkyl, alkenyl or alkynyl group, and R1 and R2 may be linked to form a ring. R3 denotes an aryl, heterocyclic, alkyl, alkenyl or alkynyl group. A denotes a hydrogen atom, alkoxy group, aryloxy group, acyloxy group or silyloxy group which may have a substituent.

  相应的α-氨基酮的制造具有高产率和高对映选择性。一种具有光学活性的α-氨基酮衍生物的制造方法，其中式(1)表示的酮与式(3)表示的亚硝基化合物在式(4)表示的脯氨酸衍生物存在下发生反应。 式中，R1 和 R2 分别表示烷基、烯基或炔基，R1 和 R2 可连接成环。R3 表示芳基、杂环基、烷基、烯基或炔基。A 表示氢原子、烷氧基、芳氧基、酰氧基或硅氧基，可带有取代基。
• Enantioselective O-Nitroso Aldol Reaction of Silyl Enol Ethers
  作者：Masanori Kawasaki、Pingfan Li、Hisashi Yamamoto

  DOI：10.1002/anie.200705679

  日期：2008.5.5
• Optically active alpha-aminooxyketone derivatives and process for production thereof
  申请人：Hayashi Yujiro

  公开号：US20060293525A1

  公开（公告）日：2006-12-28

  The corresponding α-aminooxy ketone is manufactured with a high yield and a high enantioselectivity. A manufacturing method for an optically active α-aminooxy ketone derivative expressed by formula (1), wherein a ketone expressed by formula (2) is caused to react with a nitroso compound expressed by formula (3) in the presence of a proline derivative expressed by formula (4). In the formula, R 1 and R 2 respectively denote an alkyl, alkenyl or alkynyl group, and R 1 and R 2 may be linked to form a ring. R 3 denotes an aryl, heterocyclic, alkyl, alkenyl or alkynyl group. A denotes a hydrogen atom, alkoxy group, aryloxy group, acyloxy group or silyloxy group which may have a substituent.
• US7279601B2
  申请人：——

  公开号：US7279601B2

  公开（公告）日：2007-10-09
• Catalytic Enantioselective Synthesis of α-Aminooxy and α-Hydroxy Ketone Using Nitrosobenzene
  作者：Norie Momiyama、Hisashi Yamamoto

  DOI：10.1021/ja0298702

  日期：2003.5.1

  The highly enantioselective and O-selective nitroso aldol reaction of tin enolates 2 and nitrosobenzene (1) has been developed with the use of (R)-BINAP-silver complexes as a catalyst. After the various silver salts were surveyed, the AgOTf and the AgClO4 complex were found to be optimal in the O-selective nitroso aldol reaction in both asymmetric induction (up to 97% ee) and regioselection (O/N = >99/1), affording aminooxy ketone 3. The product 3 can be transformed to alpha-hydroxy ketone 5 without any loss of enantioselectivity. Thus, the method provides an efficient approach to the catalytic enantioselective introduction of oxygen alpha- to the carbonyl group.