2,6-Dimethylcyclohexanone hydrazone | 90255-42-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,6-Dimethylcyclohexanone hydrazone
• 英文别名: Cyclohexanone, 2,6-dimethyl-, hydrazone；(2,6-dimethylcyclohexylidene)hydrazine
• CAS: 90255-42-8
• 化学式: C₈H₁₆N₂
• 分子量: 140.228
• InChiKey: QHVBLTMGLXHESL-UHFFFAOYSA-N

物化性质

• 沸点：
  228.4±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-Dimethylcyclohexanone hydrazone 在 iron(II) chloride 频哪酮 、 potassium tert-butylate 、 碘 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1,3-二甲基环己烯
  参考文献：
  名称：

  Competition of Mechanisms in Nucleophilic Substitution of Vinyl Halides. An Unequivocal Example of the Vinylic SRN1 Route1

  摘要：

  In a search for an unambiguous example of the vinylic S(RN)1 route, several vinyl bromides and iodides were reacted mostly with (-)CH(2)COCMe(3), and sometimes with (-)CH(2)COPh, (CH)-C--(Me)COEt, and (EtO)(2)PO- ions, under Fe2+- or photostimulation in Me(2)SO. Vinyl halides having vinylic hydrogens, such as beta-bromostyrene, gave acetylenic products, e.g., phenylacetylene or a tertiary PhC=C-substituted alcohol, whereas vinyl halides with allylic hydrogens, such as Me(2)C=C(I)CHMe(2), gave a substituted allene. Reduction products of the halogen, as well as substitution and rearranged substitution products, were also formed. The operation of ionic elimination-addition routes accounts for formation of most of the products, while the reduction products arise from an intermediate vinyl radical. Ph(2)C=C(Br)Ph (20) and Me(2)C=C(Br)Ph (25) gave both substitution and reduction products, but Me(2)C=C(Br)-t-Bu (23) gave only a reduction product. Formation of substitution products from the conjugated 20 and 25 was ascribed to a reaction via a vinylic S(RN)1 route, while lack of substitution in 23 is related to its nonconjugated system and to the consequent higher energy that the radical anion of the substitution product would have. The one here reported seems to be the first case of an exclusive genuine vinylic S(RN)1 process.

  DOI：

  10.1021/jo00101a045
• 作为产物：
  描述：

  二甲基环已酮 在 一水合肼 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 168.0h， 生成 2,6-Dimethylcyclohexanone hydrazone
  参考文献：
  名称：

  烯基卤化物和不饱和醇在麝香气味硫醇内酯开链类似物合成中的中继-赫克交叉偶联

  摘要：

  未活化的烯基碘化物和溴化物与一系列不同链长的烯醇进行了前所未有的钯催化中继-赫克交叉偶联，将烯烃和醇连接起来，以中等至良好的产率提供不饱和醛和酮。相比之下，烯基三氟甲磺酸酯不是该反应的合适伙伴。这种方法允许制备麝香气味剂 Vulcanolide 的开链类似物，其中一些保留了母体分子的关键嗅觉特性。

  DOI：

  10.1002/chem.202101080

文献信息

• The Suzuki Coupling Reaction in the Stereocontrolled Synthesis of 9-<i>cis</i>-Retinoic Acid and Its Ring-Demethylated Analogues^,¹
  作者：Yolanda Pazos、Beatriz Iglesias、Angel R. de Lera

  DOI：10.1021/jo010711v

  日期：2001.12.1

  thallium-accelerated Suzuki coupling reaction of tetraenyl iodide 19 and cyclohexenyl boronate 18 afforded ethyl 9-cis-retinoate (12) in high yield. Both coupling partners of the Suzuki reaction are better reacted immediately after generation from their precursors, tetraenylstannane 10 and cyclohexenyl iodide 13. The geometrically homogeneous tetraenylstannane 10, comprising the polyenic side chain of ethyl 9-cis-retinoate

  enyl加速碘化四烯基碘化物19和环己烯基硼酸酯18的Suzuki偶联反应，可高产率获得9-顺式-视黄酸乙酯（12）。Suzuki反应的两个偶合伙伴在从其前体四烯基锡烷10和环己烯基碘13生成后，立即能更好地反应。在几何上均匀的四烯基锡烷10包括9-顺-视黄酸乙酯及其环脱甲基类似物的多烯侧链。由立体选择性霍纳-沃兹沃思-埃蒙斯反应合成。另一方面，容易获得的环己酮是制备合成环修饰的9-顺-视黄酸类似物所需的环己烯基硼酸酯的理想起始原料。对于受阻的环己酮，将azo酮转化为环己烯基碘化物。然后进行碘-锂交换并用B（OMe）（3）捕集，得到环己烯基硼酸酯。如果前体环己酮具有仲碳，则通过消除在用正丁基锂处理三甲hydr时获得的C，N-二甲硅烷基化的中间体（Shapiro反应）来方便地形成烯基锂物质。上述方法均不能使2-甲基环己酮生成更多取代的有机锂。但是，交替的34和10的Stille交叉偶联得到9
• Herrmann, Wolfgang A.; Weber, Cornelia; Ziegler, Manfred L., Chemische Berichte, 1984, vol. 117, # 3, p. 875 - 894
  作者：Herrmann, Wolfgang A.、Weber, Cornelia、Ziegler, Manfred L.、Pahl, Claudia

  DOI：——

  日期：——