2-(benzylthio)-4-methoxybenzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(benzylthio)-4-methoxybenzaldehyde
• 英文别名: 2-Benzylsulfanyl-4-methoxybenzaldehyde；2-benzylsulfanyl-4-methoxybenzaldehyde
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: RBMZBFJGBNPDDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzylthio)-4-methoxybenzaldehyde 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 4.0h， 生成 N-(3-bromo-6-methoxybenzo[b]thiophen-2-yl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Step‐Economical Route to 2‐Amido‐3‐bromobenzo[ b ]thiophenes via Ynamide Formation and Selectfluor‐Mediated Oxidative Bromocyclization

  摘要：

  AbstractA one‐pot synthesis of 2‐amido‐3‐bromobenzo[b]thiophenes based on C−N coupling and oxidative bromocyclization reactions was developed. This enables a modular approach to obtain diverse substituents at the C2 position of benzothiophenes by employing structurally modified sulfonamides. Oxidative cyclization was driven by Selectfluor and represents a previously unreported recycling method for the bromide anion byproducts of the C−N bond coupling step. The details of the study are described fully herein.

  DOI：

  10.1002/ejoc.202101093
• 作为产物：
  描述：

  2-溴-4-甲氧基苯甲醛 、 苄硫醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.08h， 以88%的产率得到2-(benzylthio)-4-methoxybenzaldehyde
  参考文献：
  名称：

  Synthesis of 2,3-Dihydrobenzo[b]thiophen-3-amine 1,1-Dioxide Derivatives via LDA-Mediated Cyclization of o-(Alkylsulfonyl)benzyl Azides with Denitrogenation

  摘要：

  A new and efficient method for the synthesis of 2,3-dihydrobenzo[b]thiophen-3-amine 1,1-dioxide derivatives has been developed. Thus, treatment of o-(alkylsulfonyl)benzyl azides, which are readily obtainable from commercially available starting materials by easily operational sequences, with lithium diisopropylamide (LDA) in THE at -78 degrees C gives, after aqueous workup, 2,3-dihydrobenzo[b]thiophen-3-amine 1,1-dioxides. These products can be isolated in moderate to fair yields after N-protection with acylating agents.

  DOI：

  10.3987/com-17-13743

文献信息

• BF ₃ Mediated [1,5]‐Hydride Shift Triggered Cyclization: Thioethers Join the Game
  作者：Elvira R. Zaitseva、Alexander Yu. Smirnov、Vladimir I. Timashev、Vadim I. Malyshev、Ekaterina A. Zhigileva、Andrey A. Mikhaylov、Michael G. Medvedev、Nadezhda S. Baleeva、Mikhail S. Baranov

  DOI：10.1002/ejoc.202200547

  日期：2022.7.7

  1,5-Hydride shift triggered the cyclization of 2-(2-(benzylthio)benzylidene)malonates to thiachromanes, which are presented for the first time. Boron trifluoride as a reaction promotor is the key of this C−H activation success. Quantum chemical calculations have shown that the studied reaction proceeds via a O–BF2–O chelate, which was confirmed by NMR-analysis.

  1,5-氢化物位移触发了 2-(2-(苄硫基)亚苄基)丙二酸酯环化为硫杂色烷，这是首次提出的。三氟化硼作为反应促进剂是这种 C-H 活化成功的关键。量子化学计算表明，所研究的反应是通过O-BF 2 -O 螯合物进行的，这已通过 NMR 分析得到证实。
• Step‐Economical Route to 2‐Amido‐3‐bromobenzo[ <i>b</i> ]thiophenes <i>via</i> Ynamide Formation and Selectfluor‐Mediated Oxidative Bromocyclization
  作者：Su Jeong Hong、Chang Ju Yoon、Hee Nam Lim、Hyun‐Suk Yeom

  DOI：10.1002/ejoc.202101093

  日期：2021.11.8

  AbstractA one‐pot synthesis of 2‐amido‐3‐bromobenzo[b]thiophenes based on C−N coupling and oxidative bromocyclization reactions was developed. This enables a modular approach to obtain diverse substituents at the C2 position of benzothiophenes by employing structurally modified sulfonamides. Oxidative cyclization was driven by Selectfluor and represents a previously unreported recycling method for the bromide anion byproducts of the C−N bond coupling step. The details of the study are described fully herein.
• Synthesis of 2,3-Dihydrobenzo[b]thiophen-3-amine 1,1-Dioxide Derivatives via LDA-Mediated Cyclization of o-(Alkylsulfonyl)benzyl Azides with Denitrogenation
  作者：Kazuhiro Kobayashi、Yuuki Chikazawa、Takashi Nogi

  DOI：10.3987/com-17-13743

  日期：——

  A new and efficient method for the synthesis of 2,3-dihydrobenzo[b]thiophen-3-amine 1,1-dioxide derivatives has been developed. Thus, treatment of o-(alkylsulfonyl)benzyl azides, which are readily obtainable from commercially available starting materials by easily operational sequences, with lithium diisopropylamide (LDA) in THE at -78 degrees C gives, after aqueous workup, 2,3-dihydrobenzo[b]thiophen-3-amine 1,1-dioxides. These products can be isolated in moderate to fair yields after N-protection with acylating agents.