4-氯-2,4,6-三叔丁基-环己-2,5-二烯-1-酮 | 5457-60-3

• 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
• 中文名称: 4-氯-2,4,6-三叔丁基-环己-2,5-二烯-1-酮
• 英文名称: 4-chloro-2,4,6-tri-tert-butylcyclohexa-2,5-dienone
• 英文别名: 4-Chloro-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-one；4-chloro-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-one；4-chloro-2,4,6-tritertbutylcyclohexadienone；2,4,6-tri-tert-butyl-4-chloro-cyclohexa-2,5-dienone；2,4,6-Tri-tert-butyl-4-chlor-cyclohexa-2,5-dienon；4-Chlor-2,4,6-tri-tert.-butyl-cyclohexadien-(2,5)-on-(1)；2,4,6-Tri-tert-butyl-4-chlorocyclohexa-2,5-dien-1-one；2,4,6-tritert-butyl-4-chlorocyclohexa-2,5-dien-1-one
• CAS: 5457-60-3
• 化学式: C₁₈H₂₉ClO
• 分子量: 296.881
• InChiKey: NEQLTAGYGHWRSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  4-氯-2,4,6-三叔丁基-环己-2,5-二烯-1-酮 在 三氯一氧化钒 三氯代氧化钒(V) 作用下， 以 正己烷 为溶剂， 反应 4.0h， 生成 2,6-二叔丁基苯醌
  参考文献：
  名称：

  Harrod, John F.; Pathak, Asha, Canadian Journal of Chemistry, 1980, vol. 58, # 7, p. 686 - 693

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三叔丁基苯酚 在 氯 作用下， 生成 4-氯-2,4,6-三叔丁基-环己-2,5-二烯-1-酮
  参考文献：
  名称：

  Mueller et al., Chemische Berichte, 1954, vol. 87, p. 1605,1610

  摘要：

  DOI：

文献信息

• Chemistry of phenoxo complexes. VI. Reactions of phenoxocopper(I) complexes with carbon tetrachloride
  作者：John F. Harrod、Patrick Van Gheluwe

  DOI：10.1139/v79-147

  日期：1979.4.15

  The reactions of several substituted cuprous phenoxides with CCl4 in acetonitrile were examined. Phenoxides without ortho-substituents usually gave high yields of tetraarylorthocarbonates. It is sh...

  研究了几种取代的苯氧基亚铜与四氯化碳在乙腈中的反应。不含邻位取代基的酚盐通常会产生高产率的原碳酸四芳基酯。它是...
• Cyclodienones. X. Reaction of Halo-cyclohexadien-1-ones with Phenols in the Presence of α-Picoline and Preparation of 4-Hydroxy- and 2-Hydroxyphenyl Aryl Ethers
  作者：Masashi Tashiro、Takashi Itoh、Gouki Fukata

  DOI：10.1246/bcsj.57.416

  日期：1984.2

  Reaction of 4-halocyclohexadienones such as 4-bromo-(1a), 4-chloro-2,4,6-tri-t-butyl-(1b), 2,4-dichloro-4,6-di-t-butyl-2,5-cyclohexadien-1-one, and 2,4-dichloro-2,6-di-t-butyl-3,5-cyclohexadien-1-one with phenols in the presence of α-picoline was carried out under various conditions. The reaction of 1a and 1b with phenols afforded the corresponding 2-aryloxy-4,6-di-t-butyl phenols together with various

  4-卤代环己二烯酮如4-溴-(1a)、4-氯-2,4,6-三叔丁基-(1b)、2,4-二氯-4,6-二叔丁基的反应-2,5-环己二烯-1-酮和2,4-二氯-2,6-二叔丁基-3,5-环己二烯-1-酮在α-甲基吡啶存在下与苯酚进行各种条件。1a 和 1b 与苯酚反应得到相应的 2-芳氧基-4,6-二叔丁基苯酚以及各种副产物。由上述反应得到的 2-芳氧基-4,6-二-叔丁基-苯酚在 AlCl3 催化下发生叔丁基转移反应，得到相应的 2-羟基苯基芳基醚。4-芳氧基-2,4,6-三叔丁基-2,5-环己二烯-1-酮的类似反应也得到相应的4-羟基苯基芳基醚。
• 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。
• Electron Transfer between Protonated and Unprotonated Phenoxyl Radicals¹
  作者：Kanji Omura

  DOI：10.1021/jo701948a

  日期：2008.2.1

  [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.
• Cyclodienones. 7. Preparation and reduction of 1-(3,5-di-tert-butyl-2-hydroxyphenyl)pyridinium halides
  作者：Gouki Fukata、Takashi Itoh、Masashi Tashiro

  DOI：10.1021/jo00335a026

  日期：1981.10