1-碘-7-甲氧基萘 | 66240-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-碘-7-甲氧基萘
• 英文名称: 1-iodo-7-methoxynaphthalene
• CAS: 66240-21-9
• 化学式: C₁₁H₉IO
• 分子量: 284.096
• InChiKey: OZTHAOZBGAHYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-碘-7-甲氧基萘 在 正丁基锂 、 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， -78.0~100.0 ℃ 、413.7 kPa 条件下， 反应 16.0h， 生成 阿戈美拉汀
  参考文献：
  名称：

  A facile synthesis of melatonergic antidepressant agomelatine

  摘要：

  Agomelatine was synthesized from 8-aminonaphthalen-2-ol by diazotization-iodination, formylation, C-C bond formation by nitroaldol and Pd/C hydrogenation of beta-nitrovinylnaphthalene followed by N-acetylation. The route reported employs readily and commercially viable starting materials and reagents, and can potentially be utilized for process synthesis of agomelatine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.077
• 作为产物：
  描述：

  1-氨基-7-萘酚 在 盐酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 6.75h， 生成 1-碘-7-甲氧基萘
  参考文献：
  名称：

  A facile synthesis of melatonergic antidepressant agomelatine

  摘要：

  Agomelatine was synthesized from 8-aminonaphthalen-2-ol by diazotization-iodination, formylation, C-C bond formation by nitroaldol and Pd/C hydrogenation of beta-nitrovinylnaphthalene followed by N-acetylation. The route reported employs readily and commercially viable starting materials and reagents, and can potentially be utilized for process synthesis of agomelatine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.077

文献信息

• Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy
  作者：Ya-Nan Ding、Yan-Chong Huang、Wei-Yu Shi、Nian Zheng、Cui-Tian Wang、Xi Chen、Yang An、Zhe Zhang、Yong-Min Liang

  DOI：10.1021/acs.orglett.1c01723

  日期：2021.8.6

  We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%,

  我们描述了一种用于制备（杂）芳基硫代/硒糖苷的新型钯催化多米诺骨牌程序。容易获得的（杂）芳基碘化物和容易获得的 1-硫糖/1-硒糖被用作底物。同时，10种糖类与该反应相容，具有良好的区域选择性和立体选择性、高效率和广泛的适用性（高达89%，53例）。该方法能够直接形成（杂）芳基硫代/硒糖苷的 C(sp 2 )–S/Se 键。
• An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides
  作者：Trisha Banik、Vipul V. Betkekar、Krishna P. Kaliappan

  DOI：10.1002/asia.201801454

  日期：2018.12.4

  A direct transformation of ortho‐alkynylated aromatic vinyl ethers to 1‐iodonaphthalenes and other iodo‐heterocycles under mild Lewis acidic conditions in the presence of iodide as an external nucleophile is reported. The first example of an iodoannulation strategy using a nucleophilic source of iodine, coupled with good to excellent yields, exclusive alpha regioselectivity and a broad substrate scope

  据报道，在温和的路易斯酸性条件下，在碘化物作为外部亲核试剂的存在下，邻炔基化的芳族乙烯基醚直接转化为1-碘代萘和其他碘杂环。使用碘的亲核来源的碘环化策略的第一个例子，再加上良好至优异的产率，独特的α区域选择性和广泛的底物范围，使这项工作成为构建芳族碘化物的诱人途径。
• Selective <i>Ortho</i> Thiolation Enabled by Tuning the Ancillary Ligand in Palladium/Norbornene Catalysis
  作者：Wenqiang Cai、Zhenhua Gu

  DOI：10.1021/acs.orglett.9b00923

  日期：2019.5.3

  in organic, material, and pharmaceutical chemistry. A palladium/norbornene-catalyzed chemoselective ortho thiolation of aryl halides was reported. The selectivity of reductive elimination for C(Ar)–SR bond formation was well controlled by tuning the ancillary ligand in the aryl-NBE palladacycle Pd(IV) intermediate. The reaction showcased good substrate scope: both S-alkyl and S-aryl thiosulfonates

  在有机，材料和药物化学中，将硫基团选择性引入芳族化合物中是必不可少的且有用的。报道了钯/降冰片烯催化的芳基卤化物的化学选择性邻硫醇化。通过调节芳基-NBE丙二环钯Pd（IV）中间体中的辅助配体，可以很好地控制C（Ar）-SR键形成的还原性消除的选择性。该反应显示出良好的底物范围：S-烷基和S-芳基硫代磺酸盐都是相容的。
• Chiral Indoline‐2‐carboxylic Acid Enables Highly Enantioselective Catellani‐type Annulation with 4‐(Bromomethyl)cyclohexanone
  作者：Xin‐Meng Chen、Ling Zhu、Dian‐Feng Chen、Liu‐Zhu Gong

  DOI：10.1002/anie.202109771

  日期：2021.11.15

  Chiral indoline-2-carboxylic acid enables a highly enantioselective Catellani-type annulation of (hetero)aryl iodides, alkenyl triflate and conjugated vinyl iodides with 4-(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all-carbon bridged ring systems.

  手性二氢吲哚-2-羧酸可实现（杂）芳基碘化物、烯基三氟甲磺酸酯和共轭乙烯基碘与 4-（溴甲基）环己酮的高度对映选择性 Catellani 型环化，直接组装各种手性全碳桥环系统。
• Template Synthesis to Solve the Unreachable <i>Ortho</i> C–H Functionalization Reaction of Aryl Iodide
  作者：Bo-Sheng Zhang、Wan-Yuan Jia、Yi-Ming Wang、João C. A. Oliveira、Svenja Warratz、Ze-Qiang Zhang、Xue-Ya Gou、Yong-Min Liang、Xi-Cun Wang、Zheng-Jun Quan、Lutz Ackermann

  DOI：10.1021/acs.joc.3c02014

  日期：2023.12.1

  This report describes the use of a simple Pd/NBE catalytic system to achieve ortho C–H oxylation and phosphonylation and other functionalizations of aryl iodide through templated conversion reactions. Dimethylamine is introduced in the ortho-site of aryl iodide through C–H amination, and aryl dimethylamine is quickly converted to methyl quaternary ammonium salt precipitation. Methyl quaternary ammonium

  该报告描述了使用简单的 Pd/NBE 催化系统通过模板转化反应实现芳基碘的邻位C-H 氧基化和膦酰化以及其他功能化。通过C-H胺化在芳基碘化物的邻位引入二甲胺，芳基二甲胺迅速转化为甲基季铵盐沉淀。甲基季铵盐避免了后续官能化中的霍夫曼消除。该方法间接解决了Pd/NBE化学领域长期以来未能实现的各种芳基碘化物邻位官能化反应。