3-methoxy-4-(tosyloxy)anisole | 137669-15-9

• 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: 3-methoxy-4-(tosyloxy)anisole
• 英文别名: (2,4-Dimethoxyphenyl) 4-methylbenzenesulfonate
• CAS: 137669-15-9
• 化学式: C₁₅H₁₆O₅S
• 分子量: 308.355
• InChiKey: KGBVHQXXUCVFOO-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基苯-1,2-二醇 在 TEA 、 potassium tert-butylate 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.33h， 生成 3-methoxy-4-(tosyloxy)anisole
  参考文献：
  名称：

  The regioselective cleavage of aryl tosylates by electrochemical reduction

  摘要：

  The electrochemical reductions of eight bis(tosyloxy)benzanoid compounds were studied as a method for the regioselective cleavage of aryl tosylates. For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety. Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions. The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent. The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.

  DOI：

  10.1021/jo00029a010

文献信息

• PROCESS FOR PRODUCING AROMATIC AMINES
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20020035295A1

  公开（公告）日：2002-03-21

  The present invention provides an activator in arylamination using a palladium compound as a catalyst, which is superior to conventional phosphines in stability and performance. With the phosphine sulfide as an activator, an arylamination reaction achieves improved selectivity to produce a desired aromatic amine in an obviously increased yield as compared with a reaction using the corresponding phosphine compound. Moreover, the phosphine sulfide of the invention is impervious to oxidation and exists stably in air and therefore sufficiently withstands use on an industrial scale.

  本发明提供了一种在芳基化反应中使用钯化合物作为催化剂的活化剂，其在稳定性和性能方面优于传统的膦化合物。通过使用膦硫化物作为活化剂，芳基化反应实现了改善的选择性，以明显增加的产量生产所需的芳香胺，与使用相应的膦化合物的反应相比。此外，本发明的膦硫化物不受氧化影响，在空气中存在稳定，因此足以在工业规模上使用。
• 2,2 (Diarlyl) Vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst
  申请人：——

  公开号：US20020058837A1

  公开（公告）日：2002-05-16

  A novel 2,2-(diaryl)vinylphosphine compound represented by the following general formula (1): 1 (wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc.; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 may be the same or different and each is an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc., provided that R 4 and R 5 taken together and/or R 6 and R 7 taken together may represent a fused benzene ring, a substituted fused benzene ring, a trimethylene group, etc.; and p, q, r, and s each is 0 to 5, provided that p+q and r+s each is in the range of from 0 to 5); a palladium-phosphine catalyst obtained by causing a palladium compound to act on the novel 2,2-(diaryl)vinylphosphine compound; and a process for obtaining an arylamine, a diaryl and an arylalkyne in the presence of the palladium-phosphine catalyst.

  一种由以下通用公式（1）表示的新型2,2-(二芳基)乙烯膦化合物：其中R1是氢原子、具有1至6个碳原子的烷基基团、具有5至7个碳原子的脂环基团等；R2、R3、R4、R5、R6和R7可能相同或不同，每个是具有1至6个碳原子的烷基基团、具有5至7个碳原子的脂环基团等，但要求R4和R5一起和/或R6和R7一起可能代表融合苯环、取代融合苯环、三亚甲基基团等；p、q、r和s每个为0至5，但要求p+q和r+s分别在0至5的范围内；通过使钯化合物作用于新型2,2-(二芳基)乙烯膦化合物而获得的钯-膦催化剂；以及在钯-膦催化剂存在下获得芳胺、二芳基和芳基炔的方法。
• REACTION CATALYST FOR CROSS-COUPLING AND METHOD FOR MANUFACTURING AROMATIC COMPOUND
  申请人：HOKKO CHEMICAL INDUSTRY CO., LTD.

  公开号：US20150360214A1

  公开（公告）日：2015-12-17

  The object of the present invention is to provide a new organic phosphorus ligand that can efficiently promote cross-coupling reaction to obtain the target substance at high yield, as well as a method of manufacturing such ligand whose steric characteristics and electronic characteristics can be fine-tuned and which can be used to cause cross-coupling reaction at high yield. As a means for achieving the aforementioned object, a phosphine compound expressed by General Formula (1) below is provided. (In the formula, R 1 and R 2 are each independently a secondary alkyl group, tertiary alkyl group, or cycloalkyl group, while R 3 and R 4 are each independently a hydrogen, aliphatic group, heteroaliphatic group, aromatic group, alicyclic group, or heterocyclic group. Note that R 3 and R 4 have no phosphorus atom and that R 3 and R 4 are not both hydrogen at the same time).

  本发明的目的是提供一种新的有机磷配体，可以高效地促进交叉偶联反应，以高产率获得目标物质，以及一种制造此类配体的方法，其立体特性和电子特性可以微调，并且可以用于高产率地引起交叉偶联反应。为了实现上述目的，提供了以下通式（1）所表示的膦化合物。（在公式中，R1和R2分别独立地为二级烷基、三级烷基或环烷基，而R3和R4分别独立地为氢、脂肪基、杂原子脂肪基、芳香族、脂环族或杂环族。请注意，R3和R4不具有磷原子，并且R3和R4不同时为氢）。
• REACTION CATALYST FOR CROSS COUPLING AND METHOD FOR MANUFACTURING AROMATIC COMPOUND
  申请人：Hokko Chemical Industry Co., Ltd.

  公开号：EP2949655B1

  公开（公告）日：2019-05-15
• 2,2-(Diaryl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst
  申请人：Takasago International Corporation

  公开号：EP1167372B1

  公开（公告）日：2003-12-10