3-formyl-4,4-dimethylcyclohexanone | 65080-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-formyl-4,4-dimethylcyclohexanone
• 英文别名: 2,2-Dimethyl-5-oxocyclohexane-1-carbaldehyde
• CAS: 65080-81-1
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: OUJDGRFKUQZUGI-UHFFFAOYSA-N

物化性质

• 沸点：
  232.4±33.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 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：

  3-formyl-4,4-dimethylcyclohexanone 在 铬酸 作用下， 以 乙醚 、 水 为溶剂， 以37%的产率得到1-keto-4,4-dimethylcyclohexane-3-carboxylic acid
  参考文献：
  名称：

  Goodyear, Gary; Waring, Anthony John, Journal of Chemical Research, Miniprint, 1991, # 11, p. 2937 - 2953

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4-二甲基-2-环己基-1-酮 在 uranyl chloride Py*HClCrO₃ 作用下， 以 二氯甲烷 为溶剂， 生成 3-formyl-4,4-dimethylcyclohexanone
  参考文献：
  名称：

  金属催化的有机光反应。在氯化钛 (IV) 或氯化铀酰存在下，含有碳-氧或碳-氮多重键的化合物与醇的光反应

  摘要：

  α,β-不饱和羰基化合物和酯、环丙基酮、β-二酮、席夫碱和腈在几种醇中在氯化钛 (IV) 或氯化铀存在下进行辐照。在氯化钛 (IV) 催化的反应中，伯醇的 α-碳原子发生键形成，通常与底物的 C=X（或 C≡N）碳原子形成键，而键形成发生在氯化铀催化反应中底物的 C=C 碳原子。在几种条件下检查了反应，并提出了可能的反应方案。

  DOI：

  10.1246/bcsj.50.2714

文献信息

• Metal-catalyzed Organic Photoreactions. Photoreactions of Compounds Containing a Carbon-oxygen or Carbon-nitrogen Multiple Bond with Alcohols in the Presence of Titanium(IV) Chloride or Uranyl Chloride
  作者：Tadashi Sato、Shigeo Yoshiie、Takashi Imamura、Kazumi Hasegawa、Masayuki Miyahara、Shigeo Yamamura、Osamu Ito

  DOI：10.1246/bcsj.50.2714

  日期：1977.10

  α,β-Unsaturated carbonyl compounds and esters, cyclopropyl ketones, β-diketones, Schiff’s bases, and nitriles were irradiated in several alcohols in the presence of titanium(IV) chloride or uranyl chloride. In the titanium(IV) chloride-catalyzed reactions, the α-carbon atom of the primary alcohols underwent a bond formation, generally with the C=X (or C≡N) carbon atom of the substrates, while the bond

  α,β-不饱和羰基化合物和酯、环丙基酮、β-二酮、席夫碱和腈在几种醇中在氯化钛 (IV) 或氯化铀存在下进行辐照。在氯化钛 (IV) 催化的反应中，伯醇的 α-碳原子发生键形成，通常与底物的 C=X（或 C≡N）碳原子形成键，而键形成发生在氯化铀催化反应中底物的 C=C 碳原子。在几种条件下检查了反应，并提出了可能的反应方案。
• Formaldehyde Dialkylhydrazones as Neutral Formyl Anion and Cyanide Equivalents:  Nucleophilic Addition to Conjugated Enones
  作者：Elena Díez、Rosario Fernández、Consolación Gasch、José M. Lassaletta、José M. Llera、Eloísa Martín-Zamora、Juan Vázquez

  DOI：10.1021/jo970481d

  日期：1997.7.1

  A versatile methodology for the nucleophilic formylation and cyanation of conjugated enones is reported. The procedure is based on the use of formaldehyde dimethylhydrazone, which, acting as a neutral formyl anion equivalent, adds to preformed trialkylsilyl-enone complexes. Both 4-(silyloxy)-3-enal hydrazones 3 or deprotected 4-oxo aldehyde monohydrazones 4 can be obtained as products depending on quenching conditions. In full analogy, an asymmetric version of the reaction using chiral formaldehyde SAMP-hydrazone as a neutral synthon of the chiral formyl anion has been developed, giving rise to the corresponding adducts 5 and 6 in good yields and with excellent diastereoselectivities (de 85-greater than or equal to 98%). Ozonolysis or HCl-mediated hydrolysis of adducts 4 and 6 readily affords racemic and optically enriched 4-oxo aldehydes 7, respectively. Additionally, high-yielding MMPP-oxidative cleavage of 4-oxo hydrazones 4 and 6 has been performed to obtain Li-oxo nitriles 8 in racemic and optically enriched forms, respectively. In this way, interesting chiral bifunctional building blocks, some of them bearing newly created stereogenic quaternary centers, have been efficiently synthesized.
• Goodyear, Gary; Waring, Anthony John, Journal of Chemical Research, Miniprint, 1991, # 11, p. 2937 - 2953
  作者：Goodyear, Gary、Waring, Anthony John

  DOI：——

  日期：——