4-methoxy-4-methyl-2,6-ditert-butylcyclohexa-2,5-dienone | 2411-18-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-methoxy-4-methyl-2,6-ditert-butylcyclohexa-2,5-dienone
• 英文别名: 4-methoxy-4-methyl-2,6-di-tert-butyl-cyclohexa-2,5-dienone；2,6-di-t-butyl-4-methyl-4-methoxy-cyclohexa-2,5-dienone；2,6-di-t-butyl-4-methoxy-4-methyl-2,5-cyclohexadienone；2,6-di-tert-butyl-4-methoxy-4-methyl-cyclohexa-2,5-dienone；2,6-Di-tert-butyl-4-methoxy-4-methyl-cyclohexa-2,5-dienon；2,6-Di-tert.-butyl-4-methoxy-4-methyl-cyclohexa-2,5-dienon；2,6-Bis(1,1-dimethylethyl)-4-methyl-4-methoxycyclohexa-2,5-dien-1-one；2,6-ditert-butyl-4-methoxy-4-methylcyclohexa-2,5-dien-1-one
• CAS: 2411-18-9
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: YIYBGEMKNPZLNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-4-methyl-2,6-ditert-butylcyclohexa-2,5-dienone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,6-二叔丁基-4-甲基苯酚
  参考文献：
  名称：

  硼氢化钠对 2,6-二叔丁基对羟基苯酚的新还原

  摘要：

  用 NaBH4 还原 2,6-二叔丁基-对羟基苯酚出人意料地导致相应二氢对羟基苯酚的区域选择性和立体选择性形成。新的还原反应是通过喹氧基硼氢化物阴离子中间体进行的，该中间体调节产物中 4 位和 6 位的立体化学。产物的芳构化被叔丁基阻止。

  DOI：

  10.1246/cl.1994.961
• 作为产物：
  描述：

  2,6-二叔丁基-4-甲基苯酚 在 甲醇 、 高氯酸 、 lead dioxide 作用下， 反应 0.08h， 生成 4-methoxy-4-methyl-2,6-ditert-butylcyclohexa-2,5-dienone
  参考文献：
  名称：

  Electron Transfer between Protonated and Unprotonated Phenoxyl Radicals¹

  摘要：

  [GRAPHICS]The reaction of phenoxyl radicals with acids is investigated. 2,4,6-Tri-tert-butylphenoxyl radical (13), a persistent radical, deteriorates in MeOH/PhH in the presence of an acid yielding 4-methoxycyclohexa-2,5-dienone 18a and the parent phenol (14). The reaction is facilitated by a strong acid. Treatment of 2,6-di-tert-butyl-4-methylphenoxyl radical (2), a short-lived radical, generated by dissociation of its dimer, with an acid in MeOH provides 4-methoxycyclohexa-2,5-dienone 4 and the products from disproportionation of 2 including the parent phenol (3). A strong acid in a high concentration favors the formation of 4 while the yield of 3 is always kept high. Oxidation of the parent phenol (33) with PbO2 to generate transient 2,6-di-tert-butylphenoxyl radical (35) in AcOH/H2O containing an added acid provides eventually p-benzoquinone 39 and 4,4'-diphenoquinone 42, the product from dimerization of 35. A strong acid in a high concentration favors the formation of 39. These results suggest that a phenoxyl radical is protonated by an acid and electron transfer takes place from another phenoxyl radical to the protonated phenoxyl radical, thus generating the phenoxyl cation, which can add an oxygen nucleophile, and the phenol (eq 5). The electron transfer is a fast reaction.

  DOI：

  10.1021/jo701948a

文献信息

• Catalytic oxidation of 2,6-di-t-butyl-4-methylphenol by a supported iron complex
  作者：Narc�s Homs、Pilar Ram�rez de la Piscina、Francesc Borrull

  DOI：10.1039/c39880001075

  日期：——

  The catalytic oxidation of 2,6-di-t-butyl-4-methylphenol using a catalyst of K4[Fe(CN)6] supported on acid-modified τAl2O3 is reported.

  使用K的催化剂2,6-二-叔丁基-4-甲基苯酚的催化氧化4的[Fe（CN）6 ]负载在酸改性τAl 2 ö 3报道。
• p-Quinols and p-Quinol Ethers from 2,4,6-Trialkylphenols
  作者：Kanji Omura

  DOI：10.1055/s-0029-1217127

  日期：2010.1

  The oxidation of 2,4,6-trialkylphenols with lead(IV) oxide and 70% perchloric acid in water-acetone or in alcohols gives p-quinols or p-quinol ethers, respectively. Some nonmetallic oxidants serve the same purpose.

  2,4,6-三烷基苯酚在水-丙酮或醇中与四氧化三铅和70%高氯酸反应，分别生成对苯二酚或对苯二酚醚。一些非金属氧化剂也具有相同的作用。
• Oxidation Using Quaternary Ammonium Polyhalides. IX. Oxidation of Hindered Phenols with Benzyltrimethylammonium Tribromide
  作者：Shoji Kajigaeshi、Yukihiro Morikawa、Shizuo Fujisaki、Takaaki Kakinami、Keigo Nishihira

  DOI：10.1246/bcsj.64.1060

  日期：1991.3

  Reactions of hidered phenols, such as 2,6-di-t-butyl-4-methylphenol, 3,5-di-t-butyl-4-hydroxybenzyl alcohol, and 2,6-di-t-butylphenol, with benzyltrimethylammonium tribromide were carried out in dichloromethane in the presence of water, t-butyl alcohol, or aqueous sodium hydroxide at room temperature. Sequential reaction processes were provided by the obtained products.

  隐藏的酚类，例如 2,6-二叔丁基-4-甲基苯酚、3,5-二叔丁基-4-羟基苯甲醇和 2,6-二叔丁基苯酚与苄基三甲基三溴化铵的反应在室温下，在水、叔丁醇或氢氧化钠水溶液的存在下，在二氯甲烷中进行。所得产物提供了顺序反应过程。
• Solvolysis of 4-Halogeno-4-Alkyl-2,6-di-tert-butylcyclohexa-2,5-dienones Induced by Positive Halogen Donors as Electrophiles
  作者：Kanji Omura

  DOI：10.1071/ch13257

  日期：——

  halogen donors such as N-iodosuccinimide (NIS) induce solvolysis of dienones 1, as model 4-halogenocyclohexa-2,5-dienones, in different hydroxylic solvents (ROH), yielding the 4-RO-cyclohexa-2,5-dienones (2). The rate of the solvolysis with NIS is highly dependent on the structure of ROH. The problem of such dependency is overcome by running the reaction in ROH diluted with MeCN, a polar aprotic solvent

  正卤素供体（例如N-碘琥珀酰亚胺（NIS））在不同的羟基溶剂（ROH ）中诱导二酮1（作为模型4-卤代环己2,5-二酮）的溶剂化，生成4-RO-环己-2,5-二酮。 （2）。NIS的溶剂分解速率高度依赖于ROH的结构。通过在用极性非质子溶剂MeCN代替纯ROH稀释的ROH中进行反应，可以克服这种依赖性的问题。ROH-MeCN溶剂混合物中的反应速率几乎与ROH的结构（或极性）无关，并且反应比纯ROH更快或更明显地完成。结果表明，尽管MeCN的氢键稀释可接受性也加速了反应，但溶剂分解速度受溶剂系统极性的控制。提出了一种溶剂分解机理，涉及正卤素给体在1的卤素原子上的亲电进攻，生成4-氧代环己-2,5-二烯基阳离子中间体（8）通过速率限制的极性跃迁状态。
• Efficiency for solid-state photorearrangement of 2,5-cyclohexadienones
  作者：Yoshikatsu Ito、Hirohide Ito、Masahiro Ino、Teruo Matsuura

  DOI：10.1016/0040-4039(88)85093-7

  日期：1988.1

  Visible light irradiation of 2,5-cyclohexadienones and in the solid state resulted in quantitative transformation into two isomeric lumiketones. The reaction was more efficient for bulky (φ = 0.46) than for less bulky (φ = 0.28).

  2,5-环己二酮和固态可见光照射导致定量转化为两个同分异构的lumiketones。该反应对于大体积（φ＝ 0.46）比对较小体积（φ＝ 0.28）更有效。