1-乙酰基环己烷甲醛 | 756491-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-乙酰基环己烷甲醛
• 英文名称: 1-acetylcyclohexanecarbaldehyde
• 英文别名: Cyclohexanecarboxaldehyde, 1-acetyl-；1-acetylcyclohexane-1-carbaldehyde
• CAS: 756491-88-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: LDJZPHIXJDWQBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙酰基环己烷甲醛 在 三乙胺 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 34.33h， 生成 N-{1-[1-(2,2-difluorovinyl)cyclohexyl]ethylidene}-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles

  摘要：

  Metal enolates and enamides bearing difluoroallylic moieties underwent nucleophilic 5-endo-trig cyclization, a process considered to be disfavored according to Baldwin's rules. Whereas no C-cyclization was observed in these reactions, O- and N-cyclization proceeded exclusively to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans and -2,3-dihydropyrroles, respectively.

  DOI：

  10.1055/s-0033-1340857
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1-乙酰基环己烷甲醛
  参考文献：
  名称：

  Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles

  摘要：

  Metal enolates and enamides bearing difluoroallylic moieties underwent nucleophilic 5-endo-trig cyclization, a process considered to be disfavored according to Baldwin's rules. Whereas no C-cyclization was observed in these reactions, O- and N-cyclization proceeded exclusively to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans and -2,3-dihydropyrroles, respectively.

  DOI：

  10.1055/s-0033-1340857

文献信息

• Cyclobutanones through S_N<i>i</i>‘ Ring Closure, a Mechanistic Study
  作者：Martin A. Lovchik、Andreas Goeke、Georg Fráter

  DOI：10.1021/jo062264v

  日期：2007.3.1

  2-diethyl-3-(prop-1E-en-1-yl)cyclobutanone (S)-(E)-18 and (3R)-2,2-diethyl-3-(prop-1Z-en-1-yl)cyclobutanone (R)-(Z)-18, in a ratio of 85:15, with almost complete transfer of chirality (>97%). The absolute configuration of (S)-17 was determined by X-ray diffraction analysis of the camphanoate derivative 16. The absolute configuration of the cyclobutanone products (S)-(E)-18 and (R)-(Z)-18 was determined by Raman optical

  据报道，通过烯丙基重排（S N i '反应）进行分子内亲核取代的机理研究以及对取代的环丁酮的新的立体选择途径的报道。4,4-二烷基-5-氧代己-2- ë烯-1-基甲磺酸酯4转化为2,2-二烷基-3- vinylcyclobutanones 6被S Ñ我'环闭合。反应的立体化学分析是通过（6 S）-6-氯-3,3-二乙基庚基4 E -en-2-one（S）-17的闭环实现的，C（6）的绝对构型定义为），得到（3 S）-2,2-二乙基-3-（prop-1 E-en-1-基）环丁酮（S）-（E）-18和（3 R）-2,2-二乙基-3-（prop-1 Z -en-1-基）环丁酮（R）-（Z）-18，比例为85:15，手性几乎完全转移（> 97％）。（S）-17的绝对构型是通过对樟脑酸酯衍生物16进行X射线衍射分析确定的。环丁酮产物（S）-（E）-18和（R）-（Z）-18的绝对构型用拉曼光学活性光
• Redox-Annulation of Cyclic Amines and β-Ketoaldehydes
  作者：Weijie Chen、Daniel Seidel

  DOI：10.1021/acs.orglett.6b00151

  日期：2016.3.4

  Benzo[a]quinolizine-2-one derivatives are readily assembled from 1,2,3,4-tetrahydroisoquinoline and β-ketoaldehydes by means of a new intramolecular redox-Mannich process. These reactions are promoted by simple acetic acid and are thought to involve azomethine ylides as reactive intermediates.

  通过新的分子内氧化还原-曼尼希方法，可以容易地将1,2,3,4-四氢异喹啉和β-酮醛组装成苯并[ a ]喹啉嗪-2-酮衍生物。这些反应通过简单的乙酸促进，并被认为涉及偶氮甲亚胺作为反应性中间体。
• Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes
  作者：Anirudra Paul、N. R. Thimmegowda、Thiago Galani Cruz、Daniel Seidel

  DOI：10.1021/acs.orglett.7b03721

  日期：2018.2.2

  Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and β-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.

  吲哚里西啶和喹里西啶衍生物很容易由l-脯氨酸或(±)-哌啶酸和β-酮醛通过脱羧成环过程组装而成。这些反应由乙酸促进，并涉及偶氮甲碱叶立德作为反应中间体。
• POLYMERIZABLE COMPOUNDS AND LIQUID CRYSTAL MEDIA
  申请人：Jansen Axel

  公开号：US20120298916A1

  公开（公告）日：2012-11-29

  The invention relates to 1,1-disubstituted cyclohexane derivatives containing one or more polymerisable groups, and to liquid-crystalline media comprising at least one compound of the formula I. At least one of the polymerisable groups is located at the geminally substituted position of the cyclohexane ring. The compounds are suitable for the stabilisation of liquid-crystalline phases. Examples of polymer-stabilised blue phases are indicated.

  该发明涉及含有一个或多个可聚合基团的1,1-二取代环己烷衍生物，以及包含至少一种式I化合物的液晶介质。至少一个可聚合基团位于环己烷环的孪生取代位置。这些化合物适用于稳定液晶相。指出了聚合物稳定的蓝相的例子。
• Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Ketone Enolates: Synthesis of 5-Fluorinated 2-Alkylidene-2,3-dihydrofurans
  作者：Junji Ichikawa、Takeshi Fujita、Kotaro Sakoda、Masahiro Ikeda、Masahiro Hattori

  DOI：10.1055/s-0032-1317709

  日期：——

  3,3-Difluoroallylic ketones readily undergo nucleophilic 5-endo-trig cyclization through their metal enolates to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans. O-Cyclization exclusively occurred via intramolecular substitution of the vinylic fluorines.