1-methoxy-2-<(phenylseleno)methyl>benzene | 42778-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-2-<(phenylseleno)methyl>benzene
• 英文别名: o-<(Phenylseleno)methyl>anisole；(2-methoxybenzyl)(phenyl)selane；(2-methoxyphenyl)methyl phenyl selenide；1-Methoxy-2-(phenylselanylmethyl)benzene
• CAS: 42778-12-1
• 化学式: C₁₄H₁₄OSe
• 分子量: 277.225
• InChiKey: OZRGRVNHZLXIOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2-甲氧基苯基)-N,N-二甲基甲胺 在 caesium carbonate 、 乙腈 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 1-methoxy-2-<(phenylseleno)methyl>benzene
  参考文献：
  名称：

  苄基三甲基铵盐与二（杂）芳基二硫化物和二硒化物的无过渡金属偶联反应

  摘要：

  开发了一种新的方案，以从（手性）苄基三甲基铵盐和二（杂）芳基二硫化物或二硒化物合成（对映体富集）硫醚和硒醚。弱碱的存在促进了这些合成，并且不需要使用任何过渡金属，从而使目标产物的收率达到了良好或优异（72-94％）。使用由对映体富集的胺合成的季铵盐可生成高度对映纯的苄基硫醚和硒醚（94-99％ee），其构型与对映体富集的季铵盐相反。

  DOI：

  10.1039/d0cc05633b

文献信息

• Direct Conversion of a Benzylic Hydroxy Group into a Selenenyl Group Using the Phenyl Trimethylsilyl Selenide-Aluminum Bromide Combination.
  作者：Hitoshi ABE、Akira YAMASAKI、Takashi HARAYAMA

  DOI：10.1248/cpb.46.1311

  日期：——

  A new reagent system, phenyl trimethylsilyl selenide-aluminum bromide, was developed for the direct conversion of various benzylic hydroxy groups into a selenenyl group. Treatment of cinnamyl alcohol with this reagent system yielded 3, 4-dihydro-4-phenyl-2H-1-benzoselenin via a [3, 3]-sigmatropic rearrangement of the intermediate cinnamyl phenyl selenide.

  开发了一种新试剂体系，苯基三甲基甲硅烷基硒化物-溴化铝，用于将各种苄位羟基直接转化为硒烯基。用这种试剂体系处理肉桂醇，通过中间体肉桂基苯基硒化物的[3,3]-σ迁移重排，生成了3,4-二氢-4-苯基-2H-1-苯并硒英。
• An indium–TMSCl promoted reaction of diphenyl diselenides and aldehydes: novel routes to selenoacetals and alkyl phenyl selenides
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1016/j.tetlet.2006.06.012

  日期：2006.8

  The reaction of diphenyl diselenides with aldehydes in the presence of In–TMSCl has been investigated. Aliphatic aldehydes provide the corresponding selenoacetals, whereas aromatic aldehydes lead predominantly to alkyl phenyl selenides under the same reaction conditions. This constitutes a new approach for the synthesis of selenoacetals and selenides from aldehydes.

  研究了In-TMSCl存在下二苯二硒化物与醛的反应。脂肪醛提供相应的硒缩醛，而芳香醛在相同的反应条件下主要导致烷基苯基硒化物。这构成了从醛合成硒缩醛和硒化物的新方法。
• An indium–TMSCl promoted reaction of diphenyl diselenide and diorganyl disulfides with aldehydes: novel routes to selenoacetals, thioacetals and alkyl phenyl selenides
  作者：Brindaban C. Ranu、Amit Saha、Tanmay Mandal

  DOI：10.1016/j.tet.2008.12.079

  日期：2009.3

  The reactions of diphenyl diselenide and dialkyl disulfides with aldehydes in the presence of In–TMSCl have been investigated. Aliphatic aldehydes provide the corresponding selenoacetals and aromatic aldehydes lead predominantly to benzyl phenyl selenides on reaction with diphenyl diselenide. However, the reaction of dimethyl disulfide and diphenyl disulfide with both aromatic and aliphatic aldehydes

  研究了在In–TMSCl存在下二苯二硒化物和二烷基二硫化物与醛的反应。脂族醛提供相应的硒缩醛，而芳族醛在与二苯基二硒化物反应时主要导致苄基苯基硒化物。然而，二甲基二硫化物和二苯基二硫化物与芳族和脂族醛的反应均产生二硫缩醛。这提供了从醛合成硒缩醛，硫缩醛和硒化物的新途径。
• A New Method of Generation of .alpha.-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions
  作者：Mitsuhiro Yoshimatsu、Takashi Sato、Hiroshi Shimizu、Mikio Hori、Tadashi Kataoka

  DOI：10.1021/jo00084a017

  日期：1994.3

  Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride. Olefinic and acetylenic alpha-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds. Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j. This new utilization of alpha-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.
• Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
  作者：Fuhai Li、Dan Wang、Hongyi Chen、Ze He、Lihong Zhou、Qingle Zeng

  DOI：10.1039/d0cc05633b

  日期：——

  A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72–94%). Using quaternary ammonium salts

  开发了一种新的方案，以从（手性）苄基三甲基铵盐和二（杂）芳基二硫化物或二硒化物合成（对映体富集）硫醚和硒醚。弱碱的存在促进了这些合成，并且不需要使用任何过渡金属，从而使目标产物的收率达到了良好或优异（72-94％）。使用由对映体富集的胺合成的季铵盐可生成高度对映纯的苄基硫醚和硒醚（94-99％ee），其构型与对映体富集的季铵盐相反。