cyclohexadecanone oxime | 232614-63-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cyclohexadecanone oxime
• 英文别名: Cyclohexadecanon-oxim；N-cyclohexadecylidenehydroxylamine
• CAS: 232614-63-0
• 化学式: C₁₆H₃₁NO
• 分子量: 253.428
• InChiKey: QVHGZSFAPAAEDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclohexadecanone oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 cyclohexadecylamine
  参考文献：
  名称：

  Reactivity of electron impact ionized large-ring cycloalkylamines. Loss ofCnH2n + 1. Alkyl radicals from long-chain aliphatic compounds with a terminal enamine or ester function (lipids)

  摘要：

  AbstractLarge‐ring Cycloalkylamines rearrange after electron impact ionization into long‐chain enamines. A general mechanism is proposed for their fragmentation, and a parallel is established with the fragmentation of long‐chain esters (lipids). It is shown that the parent ions rearrange into a series of interconverting branched onium ions from which alkyl radicals are lost. The mechanism of the interconversion is discussed.

  DOI：

  10.1002/oms.1210270509
• 作为产物：
  描述：

  环十二酮 生成 cyclohexadecanone oxime
  参考文献：
  名称：

  Ruzicka et al., Helvetica Chimica Acta, 1949, vol. 32, p. 552

  摘要：

  DOI：

文献信息

• Conversion of Cyclic Aziridines and 2-Amino-1-cycloalkanols to Keto Nitriles by Using Electrogenerated Reactive Halogen Species
  作者：Sigeru Torii、Tsutomu Inokuchi、Sadahito Takagishi、Etsuji Sato、Hiromi Tsujiyama

  DOI：10.1246/cl.1987.1469

  日期：1987.7.5

  Oxidative cleavage of C(1)–C(2) bond of aziridines and 2-amino-1-cycloalkanols, giving the corresponding keto nitriles, exclusively, have been performed by oxidation with electrogenerated reactive halogen species (e.g., [Cl]+).

  对氮杂环和2-氨基-1-环烷醇的C(1)–C(2)键进行氧化裂解，专门生成相应的酮腈，已通过与电生成的反应性卤素物种（如[Cl]+）的氧化反应完成。
• METHOD FOR PRODUCING AMIDE COMPOUND
  申请人：Kugimoto Junichi

  公开号：US20130005960A1

  公开（公告）日：2013-01-03

  The present invention relates to a method for producing a high purity, high quality amide compound, particularly, lactam. A first embodiment of the present invention is characterized in that an amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol % or less based on the ketone as a starting material. A second embodiment of the present invention is characterized in that one or more compounds selected from the group consisting of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A third embodiment of the present invention is characterized in that a content of impurities having a cyclic bridge structure is controlled by using a cycloalkanone purified by recrystallization.

  本发明涉及一种生产高纯度、高质量酰胺化合物的方法，特别是内酰胺。本发明的第一实施例的特征在于，通过控制溶液中每种卤化物、醛类化合物、醇类化合物和腈类化合物在回收至肟形成步骤中的含量，使其量不超过以酮为起始物的0.4摩尔％。本发明的第二实施例的特征在于，通过氢化和/或结晶净化从酮、肟和酰胺化合物组成的化合物中选择一种或多种，以消除含有双键的杂质。本发明的第三实施例的特征在于，通过使用通过再结晶纯化的环戊酮来控制具有环桥结构的杂质的含量。
• PROCESS FOR PRODUCTION OF AMIDES OR LACTAMS
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP2006283A9

  公开（公告）日：2009-07-15

  An amide or lactam is produced by conducting a rearrangement of a corresponding oxime compound in the presence of a cyclic compound containing a structure represented by following Formula (1) as a ring constituent and a fluorinated alcohol: wherein Z represents a halogen atom or an -OR group, where R represents an organic group. Z is preferably chlorine atom. Exemplary fluorinated alcohols include fluorine-containing branched-chain aliphatic alcohols represented by following Formula (3): wherein Rf1 and Rf2 may be the same as or different from each other and each represent a perfluoroalkyl group having one to eight carbon atoms; and "n" denotes an integer of 0 to 8. According to this process, amides or lactams can be simply produced in high yields without causing large amounts of by-products.

  通过在含有以下式（1）所代表的结构的环组分和氟化醇的存在下对相应的肟化合物进行重排，可以产生酰胺或内酰胺：其中Z代表卤素原子或-OR基团，其中R代表有机基团。Z最好是氯原子。示例氟化醇包括以下式（3）所代表的含氟支链脂肪醇：其中Rf1和Rf2可以相同也可以不同，每个代表具有一至八个碳原子的全氟烷基基团；“n”表示0至8的整数。根据这个过程，可以简单地高产率地生产酰胺或内酰胺，而不产生大量副产物。
• Process for producing azine compounds and oxime compounds
  申请人：——

  公开号：US20030204084A1

  公开（公告）日：2003-10-30

  A process comprising allowing a peroxide compound represented by following Formula (2): 1 wherein R a , R b , R c and R d are the same or different and are each a hydrogen atom or a hydrocarbon group, and wherein R a and R b , R c and R d may be combined to form a ring together with the adjacent carbon atom, respectively, to react with ammonia and water to yield an azine compound represented by following Formula (3): 2 wherein R a , R b , R c and R d have the same meanings as defined above, or oxime compounds represented by following Formulae (4 a ) and/or (4 b ): 3 wherein R a , R b , R c and R d have the same meanings as defined above, in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (A) in its ring: 4 wherein X is one of an oxygen atom and an —OR group, and wherein R is one of a hydrogen atom and a hydroxyl-protecting group. This process can produce an oxime compound or an azine compound useful as a material for oxime compounds from low-cost materials by easy and simple procedures.

  一种过程包括允许由以下式（2）表示的过氧化物化合物：其中Ra、Rb、Rc和Rd相同或不同，每个都是氢原子或烃基，且Ra和Rb、Rc和Rd可以分别与相邻的碳原子结合形成环，以与氨和水反应生成由以下式（3）表示的偶氮化合物：其中Ra、Rb、Rc和Rd的含义与上述定义相同，或者在具有以下式（A）中的环中具有骨架的含氮环化合物的存在下生成由以下式（4a）和/或（4b）表示的肟化合物：其中Ra、Rb、Rc和Rd的含义与上述定义相同，在X为氧原子和-OR基团之一，R为氢原子和羟基保护基团之一的情况下。该过程可以通过简单易行的步骤从低成本材料中产生用作肟化合物材料的肟化合物或偶氮化合物。
• NOVEL COMPOUND AND PROCESS FOR PRODUCING AMIDE COMPOUND THEREWITH
  申请人：Sugimoto Tsunemi

  公开号：US20130005961A1

  公开（公告）日：2013-01-03

  The present invention provides novel cyclododecanone-O-azacyclotridecen-2-yloxime and cyclododecanone-O-azacyclotridecen-2-yloxime hydrochloride. The invention also provides a process for producing an amide compound wherein cyclododecanone-O-azacyclotridecen-2-yloxime, hydrogen chloride and/or Lewis acid or cyclododecanone-O-azacyclotridecen-2-yloxime hydrochloride are used as a rearrangement catalyst and/or a reaction starting material in a reaction step.

  本发明提供了新型的环十二酮-O-氮杂环三十二烯-2-氧肟和环十二酮-O-氮杂环三十二烯-2-氧肟盐酸盐。本发明还提供了一种生产酰胺化合物的方法，其中在反应步骤中使用环十二酮-O-氮杂环三十二烯-2-氧肟、氯化氢和/或路易斯酸或环十二酮-O-氮杂环三十二烯-2-氧肟盐酸盐作为重排催化剂和/或反应起始物质。