5-碘-2-甲基苯并[d]噻唑 | 90414-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 5-碘-2-甲基苯并[d]噻唑
• 英文名称: 5-iodo-2-methylbenzo[d]thiazole
• 英文别名: 5-iodo-2-methylbenzothiazole；5-Iodo-2-methyl-1,3-benzothiazole
• CAS: 90414-61-2
• 化学式: C₈H₆INS
• mdl: MFCD00643249
• 分子量: 275.113
• InChiKey: UUODOEGHZZBDBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  存储条件为2-8°C，避光，并充入氩气。

反应信息

• 作为反应物：
  描述：

  5-碘-2-甲基苯并[d]噻唑 在 盐酸 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-甲基苯并噻唑-5-羧酸
  参考文献：
  名称：

  Potent and orally efficacious benzothiazole amides as TRPV1 antagonists

  摘要：

  Benzothiazole amides were identified as TRPV1 antagonists from high throughput screening using recombinant human TRPV1 receptor and structure-activity relationships were explored to pinpoint key pharmacophore interactions. By increasing aqueous solubility, through the attachment of polar groups to the benzothiazole core, and enhancing metabolic stability, by blocking metabolic sites, the drug-like properties and pharmokinetic profiles of benzothiazole compounds were sufficiently optimized such that their therapeutic potential could be verified in rat pharmacological models of pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.018
• 作为产物：
  描述：

  5-氨基-2-甲基苯并噻唑 在 盐酸 、 sodium nitrite 、 potassium iodide 作用下， 以 水 为溶剂， 以61 %的产率得到5-碘-2-甲基苯并[d]噻唑
  参考文献：
  名称：

  苯并噻唑鎓盐碘代染料的合成及光谱性质

  摘要：

  摘要 合成了一系列在供体和/或受体部分含有碘原子的新型苯乙烯基型硫代碳花青染料，其电子吸收光谱位于单线态-单线态( S 0 – S 1 )和单线态-三线态( S 0 – T 1 ) 跃迁已被研究。将碘原子引入染料分子中会导致吸收最大值红移，无论碘位置如何。含有两个或两个以上碘原子的染料的电子吸收光谱在 λ 650 至 1000 nm 范围内显示出弱肩峰，这对应于单重态-三重态跃迁。

  DOI：

  10.1134/s107042802401007x

文献信息

• The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides
  作者：Jonathan T. Reeves、Kaddy Camara、Zhengxu S. Han、Yibo Xu、Heewon Lee、Carl A. Busacca、Chris H. Senanayake

  DOI：10.1021/ol500067f

  日期：2014.2.21

  react with Grignard reagents to give sulfides in good yields. The S-alkyl Bunte salts are prepared from odorless sodium thiosulfate by an SN2 reaction with alkyl halides. A Cu-catalyzed coupling of sodium thiosulfate with aryl and vinyl halides was developed to access S-aryl and S-vinyl Bunte salts. The reaction is amenable to a broad structural array of Bunte salts and Grignard reagents. Importantly

  S-烷基，S-芳基和S-乙烯基硫代硫酸钠盐（Bunte盐）与Grignard试剂反应生成硫化物，收率很高。S-烷基邦特盐是由无味的硫代硫酸钠通过与烷基卤化物的S N 2反应制备的。开发了铜催化的硫代硫酸钠与芳基卤化物和乙烯基卤化物的偶联物，以得到S-芳基和S-乙烯基丁烯酸盐。该反应适合于多种结构的邦特盐和格氏试剂。重要的是，这种硫化物的途径避免了使用恶臭的硫醇原料或副产物。
• Synthesis of Aryldiazoacetates through Palladium(0)-Catalyzed Deacylative Cross-Coupling of Aryl Iodides with Acyldiazoacetates
  作者：Fei Ye、Chengpeng Wang、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201407653

  日期：2014.10.20

  Palladium(0)‐catalyzed deacylative cross‐coupling of aryl iodides and acyldiazocarbonyl compounds can be achieved at room temperature under mild reaction conditions. The coupling reaction represents a highly efficient and general method for the synthesis of aryldiazocarbonyl compounds, which have found wide and increasing applications as precursors for generating donor/acceptor‐substituted metallocarbenes

  钯（0）催化的芳基碘化物和酰基重氮羰基化合物的脱酰基交叉偶联可在室温下在温和的反应条件下实现。偶联反应代表了合成芳基重氮羰基化合物的一种高效且通用的方法，该方法作为生成供体/受体取代的金属碳烯的前体已得到越来越广泛的应用。
• Synthesis of 2,2,2,‐Trichloroethyl Aryl‐ and Vinyldiazoacetates by Palladium‐Catalyzed Cross‐Coupling
  作者：Liangbing Fu、Jeffrey D. Mighion、Eric A. Voight、Huw M. L. Davies

  DOI：10.1002/chem.201700101

  日期：2017.3.8

  An efficient and convenient synthesis of 2,2,2‐trichloroethyl (TCE) aryl‐ and vinyldiazoacetates was achieved by palladium‐catalyzed cross‐coupling reactions between TCE diazoacetates and aryl or vinyl iodides. The broad substrate scope allows for rapid and facile formation of TCE aryl‐ and vinyldiazoacetates, which recently have emerged as versatile reagents for rhodium‐carbene chemistry.

  通过TCE重氮乙酸酯与芳基或乙烯基碘化物之间的钯催化交叉偶联反应，可以高效，方便地合成2,2,2-三氯乙基（TCE）芳基和乙烯基重氮乙酸酯。广泛的底物范围允许快速简便地形成TCE芳基和乙烯基重氮乙酸酯，最近它们已成为铑卡宾化学的多功能试剂。
• METHOD FOR PRODUCING AROMATIC COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20150322101A1

  公开（公告）日：2015-11-12

  A method is provided for producing an aromatic compound, including a step of mixing a compound represented by formula (A) and a compound represented by formula (B): in the presence of at least one phosphine compound selected from the group consisting of a phosphine represented by formula (C) and a phosphonium salt represented by formula (F): a base, a palladium compound, and an aprotic organic solvent.

  提供一种生产芳香化合物的方法，包括以下步骤：在至少一种磷化物化合物的存在下，将由化学式(A)表示的化合物与由化学式(B)表示的化合物混合；所述磷化物化合物选择自由化学式(C)表示的磷化物和由化学式(F)表示的磷酸盐；还包括碱、钯化合物和无水有机溶剂。
• METHOD FOR PRODUCING UNSATURATED ORGANIC COMPOUND
  申请人：Asaumi Taku

  公开号：US20110046380A1

  公开（公告）日：2011-02-24

  A method for producing an unsaturated organic compound represented by the formula (3): (Y 1 ) m-1 —R 1 —R 2 —(Y 2 ) n-1 (3) wherein Y 1 represents R 2 or X 1 , and Y 2 represents R 1 or B(X 2 ) 2 , which comprises reacting a compound represented by the formula (1): R 1 (X 1 ) m (1) wherein R 1 represents an aromatic group or the like, X 1 represents a leaving group and m represents 1 or 2, with a compound represented by the formula (2): R 2 B(X 2 ) 2 } n (2) wherein R 2 represents an aromatic group or the like, X 2 represents a hydroxyl group or the like, and n represents 1 or 2, in the presence of (a) a nickel compound selected from a nickel carboxylate, nickel nitrate and a nickel halide, (b) a phosphine compound such as 1,4-bis(dicyclohexylphosphino) butane, (c) an amine selected from a primary amine and a diamine such as N,N,N′,N′-tetramethyl-1,2-ethanediamine, and (d) an inorganic base.

  一种用于生产由公式(3)表示的不饱和有机化合物的方法：(Y1)m-1—R1—R2—(Y2)n-1(3)，其中Y1代表R2或X1，Y2代表R1或B(X2)2，包括在以下条件下反应由公式(1)表示的化合物：R1(X1)m(1)，其中R1代表芳香族基团或类似物，X1代表离开基团，m代表1或2，与由公式(2)表示的化合物反应：R2B(X2)2}n(2)，其中R2代表芳香族基团或类似物，X2代表羟基或类似物，n代表1或2，在存在(a)选择自镍羧酸盐、硝酸镍和卤化镍的镍化合物，(b)膦化合物，如1,4-双(二环己基膦基)丁烷，(c)选择自一次胺和二胺的胺，如N,N,N′,N′-四甲基-1,2-乙二胺，和(d)无机碱。

表征谱图