Methyl-dibenzothiophen-2-carboxylat | 22099-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: Methyl-dibenzothiophen-2-carboxylat
• 英文别名: dibenzothiophene-2-carboxylic acid methyl ester；Dibenzothiophen-2-carbonsaeure-methylester；methyl dibenzothiophene-2-carboxylate
• CAS: 22099-28-1
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: ZGKNSNCMFHUWMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl-dibenzothiophen-2-carboxylat 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以68%的产率得到3-苯基苯甲酸甲酯
  参考文献：
  名称：

  Desulfurization of benzo- and dibenzothiophenes with nickel boride

  摘要：

  Nickel boride, prepared from the reduction of nickel chloride hexahydrate with sodium borohydride in methanol-tetrahydrofuran, reduces benzothiophenes to alkylbenzenes and dibenzothiophenes to biphenyls. The reaction is rapid at or below room temperature and does not require protection from the atmosphere. Best results are obtained when the nickel boride is generated in situ in the presence of the sulfur compound. Hydroxyl, carboxyl, ester, and amino groups are unaffected while chloro, bromo, and nitro substituents are also reduced under these conditions. A short-lived intermediate, possibly a nickel hydride species, appears to be required in the desulfurization. Complexation of the substrate to the nickel boride surface, followed by stepwise reduction of the two C-S bonds, occurs. The faster disappearance of dibenzothiophene containing the lighter S-32 isotope compared to that with S-34 (k(S-32)/k(S-34) = 1.005 to 1.006) suggests that C-S bond cleavage is the rate-determining step.

  DOI：

  10.1021/jo00033a017
• 作为产物：
  描述：

  2-乙酰基二苯并噻吩 在 1,4-二氧六环 、 乙醚 、 碘 、 potassium iodide 作用下， 生成 Methyl-dibenzothiophen-2-carboxylat
  参考文献：
  名称：

  DIBENZOTHIOPHENE: ORIENTATION AND DERIVATIVES

  摘要：

  DOI：

  10.1021/jo01219a003

文献信息

• Oxidative α-C–C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O₂ at Room Temperature via Iron Photocatalysis
  作者：Zongnan Zhang、Guoxiang Zhang、Ni Xiong、Ting Xue、Junjie Zhang、Lu Bai、Qinyue Guo、Rong Zeng

  DOI：10.1021/acs.orglett.1c00556

  日期：2021.4.16

  cleavage of unfunctionalized secondary (2°) and tertiary alcohols (3°) is essential for valorization of macromolecules and biopolymers. We developed a blue-light-driven iron catalysis for aerobic oxidation of 2° and 3° alcohols to acids via α-C–C bond cleavages at room temperature. The first example of oxygenation of the simple tertiary alcohols was reported. The iron catalyst and blue light play critical

  未官能化的仲醇（2°）和叔醇（3°）的选择性α-CC键断裂对于大分子和生物聚合物的增值至关重要。我们开发了一种蓝光驱动的铁催化剂，用于在室温下通过α-CC键断裂将2°和3°醇有氧氧化为酸。报道了简单叔醇氧化的第一个例子。铁催化剂和蓝光起着至关重要的作用，可以使醇类形成高反应性的O自由基，并随后发生两次α-CC键断裂。
• 2-(substituted-dibenzofuranyl and dibenzothienyl) carbapenem
  申请人：Merck & Co., Inc.

  公开号：US05025008A1

  公开（公告）日：1991-06-18

  Carbapenems having the formula: ##STR1## where Z is; ##STR2## where X is O or S(O).sub.0-2 ; are useful antibacterial agents, especially with respect to activity against methicillin resistant Staphylococcus aureus (MRSA).

  碳青霉烯类药物的化学式为：##STR1## 其中 Z 为；##STR2## 其中 X 为 O 或 S(O).sub.0-2；对抗甲氧西林耐药金黄色葡萄球菌（MRSA）等细菌具有很好的活性。
• Intermediates for preparing 2-(substituted-dibenzo-furanyl and
  申请人：Merck & Co., Inc.

  公开号：US05132420A1

  公开（公告）日：1992-07-21

  Carbapenem intermediates having the formula: ##STR1## where Z is ##STR2## M is a removable protecting group for carboxy and P' is a removable protecting group for hydroxy, are useful intermediates for preparing antibacterial agents, especially with respect to activity against methicillin resistant Staphylococcus aureus (MRSA).

  碳青霉烯中间体具有以下化学式：##STR1## 其中 Z 为 ##STR2##，M 是羧基的可去保护基，P' 是羟基的可去保护基，这些化合物是制备抗菌药物的有用中间体，特别是对抗耐甲氧西林金黄色葡萄球菌（MRSA）活性方面。
• Intermediates for preparing 2-(substituted-dibenzofuranyl and
  申请人：Merck & Co., Inc.

  公开号：US05151512A1

  公开（公告）日：1992-09-29

  Carbapenem intermediates having the formula: ##STR1## where Z is; ##STR2## M is a removable protecting group for carboxy and P' is a removable protecting group for hydroxy are useful intermediates for preparing antibacterial agents, especially with respect to activity against methicillin resistant Staphylococcus aureus (MRSA).

  碳青霉烯中间体具有以下化学式：##STR1## 其中 Z 为；##STR2## M 是羧基的可去保护基，P' 是羟基的可去保护基，这些中间体对于制备抗菌剂特别是针对耐甲氧西林金黄色葡萄球菌（MRSA）的活性是有用的。
• Palladium(<scp>ii</scp>)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
  作者：Mamoru Tobisu、Yoshihiro Masuya、Katsuaki Baba、Naoto Chatani

  DOI：10.1039/c5sc04890g

  日期：——

  A new process has been developed for the palladium(II)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C–H and C–S bonds. In contrast to the existing methods for the synthesis of this scaffold by C–H functionalization, this new catalytic C–H/C–S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C–X or S–H

  开发了一种通过C-H 和 C-S 键裂解钯 ( II ) 催化合成二苯并噻吩衍生物的新工艺。与现有的通过 C-H 官能化合成该支架的方法相比，这种新的催化 C-H/C-S 偶联方法不需要存在外部化学计量氧化剂或反应性官能团，例如 C-X 或 S -H，允许其应用于复杂的 π 系统的合成。值得注意的是，该反应的产物形成步骤在于氧化加成步骤而不是还原消除步骤，使得该反应在机理上不常见。