5-Chlor-1,4-dihydro-1,4-epoxynaphthalin | 134456-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Chlor-1,4-dihydro-1,4-epoxynaphthalin
• 英文别名: 5-chloro-1,4-dihydro-1,4-epoxynaphthalene；3-chloro-11-oxatricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene
• CAS: 134456-78-3
• 化学式: C₁₀H₇ClO
• 分子量: 178.618
• InChiKey: KYBMHUDUZPPNTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-氯-3-碘苯 在 间氯过氧苯甲酸 、 sodium t-butanolate 作用下， 以 甲基叔丁基醚 、 水 、 乙腈 为溶剂， 反应 1.58h， 生成 5-Chlor-1,4-dihydro-1,4-epoxynaphthalin
  参考文献：
  名称：

  Aryl(TMP)iodonium Tosylate 试剂作为多种芳基中间体的战略切入点：选择性获取芳炔

  摘要：

  芳烃是广泛存在于社会重要分子中的基序。进入不同的芳烃化学空间至关重要，并且非常希望能够从普通试剂中做到这一点。甲苯磺酸芳基（TMP）碘鎓通过多种芳基中间体为芳烃化学空间提供了一个这样的接入点。在这里，我们证明控制反应途径选择性地导致芳烃具有广泛的芳烃和亲芳烃（24 个例子，平均产率 70%）和有效获取生物活性化合物。

  DOI：

  10.1021/acs.orglett.1c01534

文献信息

• A Selective C−H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine
  作者：Sunil K. Sundalam、Aleksandra Nilova、Thomas L. Seidl、David R. Stuart

  DOI：10.1002/anie.201603222

  日期：2016.7.11

  highly functionalized arynes from unsymmetrical aryl(mesityl)iodonium tosylate salts. The iodonium salts are prepared in a single pot from either commercially available aryl iodides or arylboronic acids. The aryne intermediates are generated by ortho‐C−H deprotonation of aryl(mesityl)iodonium salt with a commercially available amide base and trapped in a cycloaddition reaction with furan in moderate to good

  这里描述的是一种有效的方法，可以从不对称的芳基（间苯二甲氧基）碘化甲苯磺酸盐中获得高度官能化的芳烃。碘鎓盐在一个罐中由市售的芳基碘化物或芳基硼酸制备。亚芳基中间体是通过芳基（间苯二甲氧基）碘鎓盐与市售酰胺基的邻-CH脱质子化反应生成的，并以中等到良好的产率被捕获在与呋喃的环加成反应中。还描述了呋喃以外的芳烃中间体的偶合剂，包括叠氮化苄和脂环族胺亲核试剂。讨论了该反应的区域和化学选择性，并提出了碘鎓盐的观众芳基配体作为选择性关键控制元素的证据。
• Reaction of 1,2-dihalogen substituted arenes with lanthanum metal: a new generation method of benzyne
  作者：Hiroshi Kawabata、Toshiki Nishino、Yutaka Nishiyama、Noboru Sonoda

  DOI：10.1016/s0040-4039(02)00958-9

  日期：2002.7

  A new generation method of benzyne has been developed. When 1,2-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, Diels–Alder products between benzyne and dienes were formed in moderate to good yields.

  已经开发了新一代的苯甲醛方法。当在二烯存在下使1,2-二卤素取代的芳烃与镧金属反应时，苯并炔和二烯之间的狄尔斯-阿尔德产物形成的产率中等至良好。
• Synthesis of Alkyl Aryl Ethers by O-Arylation of Alcohols with Diaryliodonium Salts: Scope, Limitations, and Mechanism
  作者：David R. Stuart、Rory T. Gallagher、Soocheta Jha、Bryan E. Metze

  DOI：10.1055/a-2198-3637

  日期：2024.5

  6-trimethoxyphenyl)iodonium salts and aliphatic alcohols under weak base conditions. The scope of the reaction is presented, with 16 examples ranging in yield from moderate to high (54–96%). The limitations of the reaction are also presented. Mechanistic experiments reveal a complex network of reactions that include side reactions that generate arynes and oxidize the alcohol nucleophile.

  我们描述了芳基(2,4,6-三甲氧基苯基)碘鎓盐和脂肪醇在弱碱条件下发生C-O偶联反应。介绍了反应的范围，有 16 个例子，产率从中等到高 (54-96%)。还提出了该反应的局限性。机理实验揭示了一个复杂的反应网络，其中包括生成芳烃和氧化醇亲核试剂的副反应。
• Effenberger, Franz; Daub, Wolfgang, Chemische Berichte, 1991, vol. 124, # 9, p. 2113 - 2118
  作者：Effenberger, Franz、Daub, Wolfgang

  DOI：——

  日期：——
• Dehalogenation of o-dihalogen substituted arenes and α,α′-dihalogen substituted o-xylenes with lanthanum metal
  作者：Yutaka Nishiyama、Hiroshi Kawabata、Toshiki Nishino、Kouji Hashimoto、Noboru Sonoda

  DOI：10.1016/s0040-4020(03)01027-5

  日期：2003.8

  It was found that lanthanum metal caused the dehalogenation of o-dihalogen substituted arenes and alpha,alpha'-dihalogen substituted o-xylenes to generate the corresponding benzynes and o-quinodimethanes. When o-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, the Diels-Alder products between benzyne and dienes were formed in moderate to good yields. Similarly, the Diels-Alder adducts of o-quinodimethane with dienophiles were obtained, in the reaction of alpha,alpha'-dibromo-o-xylenes with lanthanum metal in the presence of dienophiles. (C) 2003 Elsevier Ltd. All rights reserved.