4-methylbenzenecarboselenoic acid | 105223-27-6

• 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: 4-methylbenzenecarboselenoic acid
• 英文别名: p-Methylselenobenzoesaeure
• CAS: 105223-27-6
• 化学式: C₈H₈OSe
• 分子量: 199.111
• InChiKey: CJGBAZJAGKVUSU-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  305.4±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-methylbenzenecarboselenoic acid 、 异氰酸苯酯 以 乙醚 为溶剂， 反应 0.33h， 以93%的产率得到4-methylbenzoyl N-phenylcarbamoyl selenide
  参考文献：
  名称：

  酰基氨基甲酰基硒化物和相关硫同系物：合成和 X 射线结构分析

  摘要：

  发现硒羧酸 [RC(=O)SeH] 容易与芳基、酰基和芳烃磺酰基异氰酸酯反应生成相应的酰基氨基甲酰基硒化物 3 [RC(=O)SeC(=O)NHR', R' = 芳基， C6H5CO 和 4-MeC6H4SO2] 收率良好。它们的互变异构体 [RC(=O)SeC(=NR')OH] 也被 1H、13C 和 77Se NMR 光谱检测到。3 [R = 2,6-(MeO)2C6H3, R' = 4-MeC6H4] 的结构通过 X 射线晶体学表征，表明该分子通过羰基氧和 NH 之间的分子内氢键稳定氢形成平面六元环，并通过邻甲氧基氧与羰基氧或硒原子的非键相互作用。4-甲氧基苯甲酰基和 4-甲氧基硫代苯甲酰基 N-（4-甲基苯基）氨基甲酰基硫化物（4 和 5）通过 X 射线晶体学显示同样具有由羰基氧或硫羰基硫之间的氢键形成的平面分子内六元环和 NH 氢原子。互变异构体 [RC(=E)SC(=NR')OH;

  DOI：

  10.1002/hc.1040
• 作为产物：
  描述：

  sodium 4-methylbenzenecarboselenoate 在 air 、 水 作用下， 以 Petroleum ether 为溶剂， 反应 3.0h， 生成 4-methylbenzenecarboselenoic acid
  参考文献：
  名称：

  Kato, Shinzi; Kageyama, Hideki; Kawahara, Yasuyuki, Chemische Berichte, 1992, vol. 125, # 2, p. 417 - 422

  摘要：

  DOI：

文献信息

• THE SYNTHESES OF POTASSIUM SELENOCARBOXYLATES AND THEIR DERIVATIVES
  作者：Hideharu Ishihara、Yoshio Hirabayashi

  DOI：10.1246/cl.1976.203

  日期：1976.3.5

  Potassium selenocarboxylates were prepared in good yields on the reaction of diacyl selenides with methanolic potassium hydroxide. They were fairly stable under nitrogen and useful as starting material for the preparation of selenocarboxylic acid derivatives; methyl selenobenzoate, α-(selenobenzoyl)acetophenone, phenyl p-chlorobenzoyl diselenide, O-trimethylsilyl selenobenzoate, bis(selenostearoyl)methane, and dibenzoyl diselenide.

  在甲醇钾与二酰基硒反应下，成功制备了高产率的钾硒羧酸盐。这些化合物在氮气环境下相当稳定，并且可作为制备硒羧酸衍生物的起始材料，包括甲基硒苯甲酸酯、α-（硒苯甲酰基）乙酰苯、苯基对氯苯甲酰二硒化物、O-三甲基硅基硒苯甲酸酯、双（硒硬脂酰基）甲烷，以及二苯甲酰二硒化物。
• Group 13 metal carbochalcogenoato complexes: Synthesis, X-ray structure analysis, and reactions
  作者：Norio Nakata、Shinzi Kato、Osamu Niyomura、Masahiro Ebihara

  DOI：10.1002/hc.21445

  日期：2018.12

  AbstractA series of alkali metal tetrakis(carbochalcogenoato)‐gallates and ‐indates M[M′(EOCR)4](solv.) (M = alkali metal; M′ = Ga, In; E = S, Se) and tris(carbodithioato)aluminum, ‐gallates and ‐indates M′ (SSCR)3 (M′ = Al, Ga, In) were prepared by the reactions of alkali metal carbochalcogenate with metal trihalogenides (M′X3; M′ = Al, Ga, In; X = Cl, Br) and by those of piperidinium carbodithioates or carbodithioic and carboselenoic acids with M′X3, respectively. An X‐ray molecular structure analysis revealed that they have an acetone molecule as a crystal solvent. The reactions of the potassium complexes K[M′ (EOCR)4](H2O) (E = S, Se) with methanol and primary and secondary amines gave the corresponding methyl ester and amides in good yields, while the reactions with iodomethane and iodine gave S‐ and Se‐methyl chalcogenoesters RCOEMe (E = S, Se) in good yields. Similar reactions of the tris(carbodithioato)gallates and ‐indates led to the corresponding O‐methyl thioesters, thioamides, and S‐methyl dithioesters in moderate to good yields. Oxidation of the tetrakis‐ and tris‐derivatives with iodine afforded the corresponding diacyl dichalcogenides (RCOE)2 (E = S, Se) and di(carbothioyl) disulfides in quantitative yields. These reactions appeared to occur on the carbonyl or selenium atom of the tetrakis compounds and on the sulfide sulfur or thiocarbonyl carbon atom of the tris‐compounds, respectively. A possible mechanism for these I2‐oxidation reactions is discussed.