2-Methyl-3-n-butyl-1,4-naphthalenedione | 2397-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Methyl-3-n-butyl-1,4-naphthalenedione
• 英文别名: 2-butyl-3-methylnaphthalene-1,4-dione；3-butyl-2-methylnaphthalene-1,4-dione；2-Methyl-3-butyl-1,4-naphthoquinone
• CAS: 2397-62-8
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: BXRGMKVTCTWHRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-Methyl-3-n-butyl-1,4-naphthalenedione 在 N-benzylcinchonidinum chloride sodium hydroxide 、 双氧水 作用下， 以 水 、 甲苯 为溶剂， 以35%的产率得到(-)-2-Methyl-3-butyl-1,4-naphthoquinone 2,3-epoxide
  参考文献：
  名称：

  Catalytic asymmetric induction in oxidation reactions. Synthesis of optically active epoxynaphthoquinones

  摘要：

  DOI：

  10.1021/jo01300a047
• 作为产物：
  描述：

  3-n-Butyl-2-methyl-4-methoxy-4-phenyl-2-cyclobutenone 在 ammonium cerium(IV) nitrate 作用下， 生成 2-Methyl-3-n-butyl-1,4-naphthalenedione
  参考文献：
  名称：

  A strategy for generalization of the regiospecific synthesis of substituted quinones from cyclobutenediones

  摘要：

  Documented within is a straightforward protocol for the synthesis of generally substituted benzoquinones and ring-fused quinones. Previously, the crucial issue of quinone substituent regiochemistry was resolved at the stage of addition of an unsaturated carbon nucleophile to a cyclobutenedione by using either symmetrically substituted cyclobutenediones or 3-alkoxy (or amino)-4-substituted-3-cyclobutenediones. In the former case there are no regioisomeric quinones formed, while in the latter, through resonance delocalization, the alkoxy (or amino) substituent renders one of the two carbonyl groups less reactive and directs the incoming nucleophile to the other. The placement of a wide variety of substituents about the quinone ring periphery has now been solved by the less restrictive strategy of sequential introduction of substituents onto a cyclobutenedione core. The chemistry commences with 3-isopropoxy-4-substituted-3-cyclobutene-1,2-diones. Addition of an aromatic, heteroaromatic, or alkenyl nucleophile to the more reactive carbonyl group provides 4-hydroxy-4-R(unsat)-2-cyclobutenones, which are protected as the methyl ethers by treatment with MeI/Ag2O/K2CO3 in MeCN. A second nucleophile is added, again in a 1,2-sense, providing highly substituted 3-isopropoxy-2-cyclobutenols that are arranged to cyclobutenones under acidic conditions. The resulting cyclobutenones are converted into substituted quinones by thermolysis at 140-degrees-C in o-xylene followed by oxidative workup with ceric ammonium nitrate. The substitution pattern about the quinone core is rigorously controlled by the sequence of introduction of the substituents.

  DOI：

  10.1021/jo00042a009

文献信息

• Synthesis and biological evaluation of vitamin K derivatives as angiogenesis inhibitor
  作者：Tomoko Kayashima、Masaharu Mori、Ryo Mizutani、Kazuyuki Nishio、Kouji Kuramochi、Kazunori Tsubaki、Hiromi Yoshida、Yoshiyuki Mizushina、Kiminori Matsubara

  DOI：10.1016/j.bmc.2010.07.022

  日期：2010.9

  Ten vitamin K3 derivatives were synthesized and screened for anti-angiogenic activity. Results indicated that amine derivatives (1a–d) exerted a stronger inhibition effect on angiogenesis compared to alkyl derivatives (2a–d). In addition to being the most potent inhibitor, 1b also suppressed human umbilical vein endothelial cell tube formation and proliferation. These results suggest that vitamin K3

  合成了十种维生素K 3衍生物，并筛选了抗血管生成活性。结果表明，与烷基衍生物（2a - d）相比，胺衍生物（1a - d）对血管生成具有更强的抑制作用。1b除了是最有效的抑制剂外，还抑制了人脐静脉内皮细胞管的形成和增殖。这些结果表明，具有较短烷基链的维生素K 3胺衍生物（例如1b）可用于开发抗血管生成剂。
• Alkyne Competition in the Benzannulation Reaction with Chromium Carbene Complexes
  作者：Chunrui Wu、Dmytro O. Berbasov、William D. Wulff

  DOI：10.1021/jo100433k

  日期：2010.7.2

  The benzannulation reaction of Fischer carbene complexes is investigated under conditions where the reaction of the carbene complex is occurring in the presence of two different alkynes. A series of competition experiments are examined where the effects of various structural factors are explored by pitting 10 different carbene complexes with 11 different alkynes. Terminal alkynes will react selectively

  在两种不同炔烃存在的情况下，在卡宾配合物的反应发生的条件下研究了费歇尔卡宾配合物的苯环化反应。考察了一系列竞争实验，其中通过将10种不同的卡宾配合物与11种不同的炔烃进行点蚀来探索各种结构因素的影响。在所有检查的情况下，包括芳基和烯基配合物，末端炔烃将比内部炔烃选择性反应。具有甲氧基取代基的芳基卡宾配合物对末端炔烃的选择性不如对内炔烃（〜95：5）的异丙醇取代基（> 99：1）的高，而大多数烯基配合物对两个取代基的选择性都很高（> 99： 1）。在两个不同的末端炔烃之间或两个不同的内部炔烃之间的竞争实验所产生的结果最多不过是非常适度的选择性（〜2：1）。如果一个末端乙炔中的一个被三甲基甲硅烷基保护，则在两个不同的末端乙炔之间可以实现极好的选择性。最后，证明了末端炔烃和内部炔烃之间的高选择性可用于与包含两种类型的炔烃功能的分子的反应。
• Therapeutic compounds and methods
  申请人：UNIVERSITY OF TASMANIA

  公开号：US10934253B2

  公开（公告）日：2021-03-02

  The invention relates to compounds of Formula (I) and methods for their preparation. Also described are pharmaceutical compositions comprising a compound of Formula (I) and their use in the treatment or prevention of conditions associated with mitochondrial dysfunction. Formula (I)

  本发明涉及式（I）化合物及其制备方法。还描述了包含式（I）化合物的药物组合物及其在治疗或预防线粒体功能障碍相关疾病中的用途。式 (I)
• Threadgill, Michael D., Synthetic Communications, 1989, vol. 19, # 1, 2, p. 167 - 172
  作者：Threadgill, Michael D.

  DOI：——

  日期：——
• THREADGILL, MICHAEL D., SYNTH. COMMUN., 19,(1989) N-2, C. 167-172
  作者：THREADGILL, MICHAEL D.

  DOI：——

  日期：——