2,3-naphthoquinone-3-methide | 79219-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-naphthoquinone-3-methide
• 英文别名: 3-Methylidenenaphthalen-2(3H)-one；3-methylidenenaphthalen-2-one
• CAS: 79219-98-0
• 化学式: C₁₁H₈O
• 分子量: 156.184
• InChiKey: BZEFTNYTOWFMLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-naphthoquinone-3-methide 在 水 作用下， 生成 3-(羟基甲基)萘-2-醇
  参考文献：
  名称：

  邻萘醌甲基化物在水溶液中的光化学生成和反应性

  摘要：

  辐照 3-羟基-2-萘甲醇 (3a) 和 2-羟基-1-萘甲醇 (4a) 导致高效（Phi(254) = 0.17 和 0.20）脱水并形成异构萘醌甲基化物，2,3-萘醌-3-methide (1) 和 1,2-naphthoquinone-1-methide (2)，分别。在水溶液中，萘醌甲基化物 1 和 2 经历快速水合以再生起始材料（tau(H2O) (1) = 7.4 ms 和 tau(H2O) (2) = 4.5 ms 在 25 摄氏度）。水合反应由氢氧根离子强烈催化，但仅在 pH < 1 时才显示出酸催化作用。反应性中间体 1 和 2 可以被其他亲核试剂拦截，例如叠氮离子 (k(N3)(1) = 2.0 x 10( 4) M(-1) s(-1) 和 k(N3)(2) = 3.0 x 10(4) M(-1) s(-1)) 或硫醇 (k(SH)(1) = 2.2 x 10(5) M(-1)

  DOI：

  10.1021/ja9031924
• 作为产物：
  描述：

  3-(羟基甲基)萘-2-醇 生成 2,3-naphthoquinone-3-methide
  参考文献：
  名称：

  Selective and reversible photochemical derivatization of cysteine residues in peptides and proteins

  摘要：

  具有3-(羟甲基)-2-萘酚基团（NQMP）的底物可以高效且选择性地与肽和蛋白质中暴露在溶剂中的半胱氨酸残基进行光连接。

  DOI：

  10.1039/c3sc51691a

文献信息

• METHODS FOR REACTING CYSTEINE RESIDUES IN PEPTIDES AND PROTEINS
  申请人：University of George Risearch Foundation, Inc.

  公开号：US20140054163A1

  公开（公告）日：2014-02-27

  Methods for labeling or modifying cysteine residues in proteins and/or enzymes are disclosed. The methods include the reaction of an o-naphthoquinone methide with a thiol group of a cysteine residue of a protein or enzyme, which can be reversible in preferred embodiments. The o-naphthoquinone methide can conveniently be generated by irradiation of a precursor compound, preferably in an aqueous solution, suspension, or dispersion.

  本文公开了用于标记或修饰蛋白质和/或酶中半胱氨酸残基的方法。该方法包括将o-萘醌甲烷与蛋白质或酶的半胱氨酸残基的巯基发生反应，而在优选实施例中，此反应是可逆的。o-萘醌甲烷可以方便地通过辐照前体化合物生成，优选地在水溶液、悬浮液或分散液中。
• Methods for Labeling a Substrate Using a Hetero-Diels-Alder Reaction
  申请人：Popik Vladimir V.

  公开号：US20110257047A1

  公开（公告）日：2011-10-20

  Methods for labeling a substrate using a hetero-Diels-Alder reaction are disclosed. The hetero-Diels-Alder reaction includes the reaction of an o-quinone methide (e.g., an o-naphthoquinone methide) with a polarized olefin to form a hetero-Diels-Alder adduct. The o-quinone methide or the polarized olefin can be attached to a surface of a substrate, and the other of the o-quinone methide or the polarized olefin can include a detectable label. The o-quinone methide can conveniently be generated by irradiation of a precursor compound, preferably in an aqueous solution, suspension, or dispersion.

  本发明揭示了使用杂Diels-Alder反应标记底物的方法。杂Diels-Alder反应包括o-醌甲烷（例如o-萘醌甲烷）与极性烯烃反应，形成杂Diels-Alder加合物。o-醌甲烷或极性烯烃可以附着在底物的表面上，而另一个o-醌甲烷或极性烯烃可以包含可检测的标签。o-醌甲烷可以方便地通过辐照前体化合物（最好是在水溶液、悬浮液或分散液中）产生。
• Wellbore Servicing Compositions and Methods of Making and Using Same
  申请人：HALLIBURTON ENERGY SERVICES, INC.

  公开号：US20140213490A1

  公开（公告）日：2014-07-31

  A method of servicing a wellbore in a subterranean formation comprising placing a wellbore servicing fluid comprising a coupling agent, a hardenable resin and a hardening agent into the wellbore wherein the coupling agent comprises a multihydroxy phenyl, a dihydroxy phenyl, a trihydroxy phenyl, ascorbic acid, a hydroxymethylnaphthol, an oxidation product thereof, a derivative thereof, or combinations thereof. A wellbore servicing fluid comprising a coupling agent, a hardenable resin, a hardening agent and a proppant wherein the coupling agent comprises a multihydroxy phenyl, a dihydroxy phenyl, a trihydroxy phenyl, ascorbic acid, a hydroxymethylphenol, a hydroxymethylnaphthol, an oxidation product thereof, a derivative thereof, or combinations thereof.
• PHOTOACID COMPOUNDS, AND RELATED COMPOSITIONS, METHODS AND SYSTEMS
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140311890A1

  公开（公告）日：2014-10-23

  A photoacid compound having a light absorbing moiety attaching a payload moiety through a linker, in which the linker comprises a geminal dialkyl linked to a carbonyl group attaching the payload moiety, and the linker is configured to present the carbonyl oxygen for reaction with a hydroxyl group presented on the light absorbing moiety in ortho position to the linker.
• US9090542B2
  申请人：——

  公开号：US9090542B2

  公开（公告）日：2015-07-28