4’-bromospiro[tetrahydrofuran-2,2’-(1’H-naphthaline)]-1’,5-dione | 1169766-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4’-bromospiro[tetrahydrofuran-2,2’-(1’H-naphthaline)]-1’,5-dione
• 英文别名: 4'-bromo-3,4-dihydro-1'H,5H-spiro[furan-2,2'-naphthalene]-1',5-dione；4'-bromo-3,4-dihydrospiro[furan-2(5H),2'(1'H)-naphthalene]-1',5-dione；4-Bromospiro[naphthalene-2,5'-oxolane]-1,2'-dione
• CAS: 1169766-36-2
• 化学式: C₁₃H₉BrO₃
• 分子量: 293.117
• InChiKey: RJSMQCKTFKPADY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-bromo-1-hydroxynaphthalen-2-yl)propionic acid 在 sodium hypochlorite pentahydrate 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 以91%的产率得到4’-bromospiro[tetrahydrofuran-2,2’-(1’H-naphthaline)]-1’,5-dione
  参考文献：
  名称：

  Practical Oxidative Dearomatization of Phenols with Sodium Hypochlorite Pentahydrate

  摘要：

  本研究首次报道了利用五水次氯酸钠作为廉价的强氧化剂对苯酚进行高效实用的氧化脱芳烃反应。氧化反应在有水存在的情况下进行得非常迅速，能以极高的产率得到所需的产物，氯化钠和水是氧化剂产生的唯一副产物。

  DOI：

  10.1246/cl.141130

文献信息

• Dearomatization of Electron‐Deficient Phenols to <i>ortho</i> ‐Quinones: Bidentate Nitrogen‐Ligated Iodine(V) Reagents
  作者：Xiao Xiao、Nathaniel S. Greenwood、Sarah E. Wengryniuk

  DOI：10.1002/anie.201909868

  日期：2019.11.4

  ortho‐quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen‐ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)‐HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho‐quinone products was examined, resulting in a facile one‐pot synthesis

  尽管其用途广泛，邻醌的合成仍然是一个重大挑战，特别是获得缺电子衍生物仍然是一个未解决的问题。这里报道了第一个通过酚类直接氧化合成缺电子邻醌的通用方法。该反应是通过一种新型双齿氮连接碘 (V) 试剂实现的，这是一类以前未开发的化合物，我们将其称为 Bi( N )-HVI。该反应非常普遍，并且对于邻位异构体和对位异构体具有优异的区域选择性。对邻醌产物的官能化进行了检查，从而实现了儿茶酚的简单一锅合成，以及多种杂原子亲核试剂的掺入。该方法代表了 Bi( N )-HVI的首次合成应用，并展示了它们作为进一步开发高反应性、高度可调的 I(V) 试剂的平台的潜力。
• METHOD FOR PRODUCING AROMATIC COMPOUND HAVING RING STRUCTURE THAT INCLUDES NITROGEN ATOM OR OXYGEN ATOM
  申请人：Ishihara Kazuaki

  公开号：US20130338371A1

  公开（公告）日：2013-12-19

  The invention is a method for efficiently producing an aromatic compound by an intramolecular cyclization reaction, the aromatic compound having a ring structure that includes a nitrogen atom or oxygen atom. An aromatic compound composed of tert-butyl-2-(3-oxo-3-phenylpropyl)phenyl carbamate or another aniline derivative or the like, or an aromatic compound composed of 3-(1-hydroxynaphthalene-2-yl)propionic acid or another naphthol derivative or the like is made to react in a system to which an oxidizing agent and a quaternary ammonium salt represented by general formula (1) are fed. In the formula, X is an iodine atom; and R 1 , R 2 , R 3 and R 4 are each independently a C 1-30 hydrocarbon group in which some hydrogen atoms are optionally substituted with halogen atoms, or R 1 and R 2 may be combine to form a divalent organic group bonded to a nitrogen atom, and R 3 and R 4 may combine to form a divalent organic group bonded to a nitrogen atom.

  该发明是一种通过分子内环化反应高效生产含有环结构的芳香化合物的方法，所述芳香化合物具有包含氮原子或氧原子的环结构。将由叔丁基-2-(3-氧代-3-苯基丙基)苯基氨基甲酸酯或其他苯胺衍生物等组成的芳香化合物，或者由3-(1-羟基萘基)丙酸或其他萘酚衍生物等组成的芳香化合物，在供应有氧化剂和由通式(1)代表的季铵盐的体系中反应。在该式中，X是碘原子；R1、R2、R3和R4分别独立地是C1-30烃基，其中一些氢原子可以选择性地被卤素原子取代，或者R1和R2可以结合形成与氮原子结合的二价有机基，R3和R4可以结合形成与氮原子结合的二价有机基。
• Chiral Ammonium Hypoiodite-catalyzed Enantioselective Oxidative Dearomatization of 1-Naphthols Using Hydrogen Peroxide
  作者：Muhammet Uyanik、Niiha Sasakura、Erina Kaneko、Kento Ohori、Kazuaki Ishihara

  DOI：10.1246/cl.141012

  日期：2015.2.5

  A highly enantioselective oxidative dearomatization of 1-naphthol derivatives (Kita spirolactonization) catalyzed by chiral hypoiodite species prepared in situ from chiral quaternary ammonium iodid...

  由手性季铵碘化物原位制备的手性次碘酸盐物种催化的 1-萘酚衍生物的高度对映选择性氧化脱芳构化（Kita 螺内酯化）...
• Efficient Phenolic Oxidations to Construct ortho-Spirolactone Structures Using Oxo-Bridged Hypervalent Iodine(III) Compound
  作者：Yasuyuki Kita、Naoko Takenaga、Teruyoshi Uchiyama、Daishi Kato、Hiromichi Fujioka、Toshifumi Dohi

  DOI：10.3987/com-10-s(e)79

  日期：——

  The intramoleular ortho-spirocyclization of naphthols 1 bearing carboxylic acid moieties as internal nucleophiles using hypervalent iodine reagents is described. The use of the mu-oxo-bridged hypervalent iodine(III) compound is remarkably effective for this transformation, and spirolactones 2 were obtained in good to excellent yields using the mu-oxo-bis[trifluoroacetato(phenyl)iodine] 4 [PhI(OCOCF(3))O(OCOCF(3))IPh].
• US9018394B2
  申请人：——

  公开号：US9018394B2

  公开（公告）日：2015-04-28