3-甲氧基-5-叔丁基-1,4-苯醌 | 2300-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲氧基-5-叔丁基-1,4-苯醌
• 英文名称: 2-Tert-butyl-6-methoxybenzoquinone
• 英文别名: 3-methoxy-5-tert-butyl-1,4-benzoquinone；2-(tert-butyl)-6-methoxycyclohexa-2,5-diene-1,4-dione；2-tert-Butyl-6-methoxy-1,4-benzochinon；6-Methoxy-2-tert.-butyl-benzochinon-(1.4)；2-Methoxy-6-tert.-butyl-1,4-benzochinon；2-Methoxy-6-t-butyl-p-benzochinon；2-tert.Butyl-6-methoxy-p-chinon；Pssfpsfnmnxhkh-uhfffaoysa-；2-tert-butyl-6-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 2300-74-5
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: PSSFPSFNMNXHKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲氧基-5-叔丁基-1,4-苯醌 在 sodium hydroxide 、 氧气 作用下， 生成 2-tert-butyl-6-hydroxy-p-benzoquinone
  参考文献：
  名称：

  Gierer,J. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1977, vol. 31, p. 561 - 572

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Hydroxy-3,5-dimethoxy-1-t-butyl-benzol 在 三氯化铁 作用下， 以 丙酮 为溶剂， 生成 3-甲氧基-5-叔丁基-1,4-苯醌
  参考文献：
  名称：

  Cuntze,U.; Musso,H., Chemische Berichte, 1970, vol. 103, p. 62 - 70

  摘要：

  DOI：

文献信息

• A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
  作者：Wanwan Yu、Per Hjerrild、Kristian M. Jacobsen、Henriette N. Tobiesen、Line Clemmensen、Thomas B. Poulsen

  DOI：10.1002/anie.201805580

  日期：2018.7.26

  functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine‐26 is presented.

  理想情况下，杂原子取代的对苯醌的制备是通过直接添加亲核试剂，然后进行原位再氧化来完成的。尽管是一种引人注目的策略，但对p-醌部分的反应性不容易驯服，也没有广泛适用的杂原子官能化方法。这里示出的是，钴（OAC）2和Mn（OAc）3 ⋅2ħ 2 ö充当强大催化剂氧化p为O，N的集合-quinone官能化，和S的亲核试剂，使用氧作为氧化剂终端。介绍了初步的机械观察结果和细胞毒性天然产物Strongylophorine-26的首次合成。
• Model Studies of Topaquinone-Dependent Amine Oxidases. 1. Oxidation of Benzylamine by Topaquinone Analogs
  作者：Minae Mure、Judith P. Klinman

  DOI：10.1021/ja00139a002

  日期：1995.8

  The aerobic oxidation of benzylamine by model compounds of topaquinone, the active site organic cofactor in copper-containing amine oxidases, was studied in order to elucidate the chemical function of the cofactor in substrate oxidation. In this study, topaquinone hydantoin (1(ox)) and a series of 2-hydroxy-5-alkyl-1,4-benzoquinones which differ in the bulk of their alkyl substituent (5, 6, 7, and 8) were employed as model compounds of the cofactor. The p-quinones (9, 10, 11, and 12) and the o-quinones (13 and 14) were prepared in order to compare them to the topaquinone analogs. Benzylamine was oxidized by the topaquinone analogs (1(ox), 5, 6, 7, and 8) to yield N-benzylidenebenzylamine (PhCH=NCH(2)Ph) as a sole product in acetonitrile at room temperature, The quinones bearing a bulky substituent (1(ox), 5, and 6) were found to be more efficient catalysts than those bearing a small primary alkyl group (7 and 8). In the latter case, the dimers (16 and 17) of the substrate Schiff base intermediates (15, R = methyl, ethyl) were isolated. The p-quinones (9, 10, 11, and 12) were catalytically inactive, The o-quinones (13 and 14) had detectable catalytic activity at room temperature, In anaerobic reactions of the o-quinones (13 and 14) with benzylamine, quantitative formation of the product (PhCH=NCH(2)Ph) was observed. For both o-quinones, products and intermediates which support a transamination mechanism were identified by H-1 NMR spectroscopy. The order of reactivity of quinones (5 > 14 > 13) reflects their redox potentials, such that regeneration of quinone may be rate-determining with o-quinones. These results demonstrate a substantial role of the 2-hydroxyl group of the topaquinone in preventing the formation of Michael adducts with substrate amine and in facilitating the reoxidation of aminoresorcinol intermediates.
• I-Oxydation catalytique des hydroxymethyl-2 phenols par des systemes MnCln/M0/O2 (M = Cu, Fe)
  作者：Daniel Sparfel、Joële Baranne-Lafont、Nguyen Kim Cuong、Patrice Capdevielle、Michel Maumy

  DOI：10.1016/s0040-4020(01)81362-4

  日期：1990.1
• Gierer,J. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1977, vol. 31, p. 561 - 572
  作者：Gierer,J. et al.

  DOI：——

  日期：——
• Cuntze,U.; Musso,H., Chemische Berichte, 1970, vol. 103, p. 62 - 70
  作者：Cuntze,U.、Musso,H.

  DOI：——

  日期：——

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