bis(4-methylbenzoic) selenoanhydride | 65212-13-7

• 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: bis(4-methylbenzoic) selenoanhydride
• 英文别名: 4-methylselenobenzoic anhydride；p-methylselenobenzoic anhydride；bis(4-methylbenzoyl) selenide；di-p-toluoyl selenide；Di-p-toluylselenid；Se-(4-methylbenzoyl) 4-methylbenzenecarboselenoate
• CAS: 65212-13-7
• 化学式: C₁₆H₁₄O₂Se
• 分子量: 317.246
• InChiKey: USSFVNNXKDYTNL-UHFFFAOYSA-N

物化性质

• 熔点：
  109.6-111.2 °C
• 沸点：
  454.8±48.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(4-methylbenzoic) selenoanhydride 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 4-methylbenzenecarboselenoic acid
  参考文献：
  名称：

  THE SYNTHESES OF POTASSIUM SELENOCARBOXYLATES AND THEIR DERIVATIVES

  摘要：

  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。

  DOI：

  10.1246/cl.1976.203
• 作为产物：
  描述：

  对甲基苯甲酰氯 在 LiAlHSeH 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到bis(4-methylbenzoic) selenoanhydride
  参考文献：
  名称：

  Reactions of acyl chlorides with LiAlHSeH. Preparation of diacyl selenides, diacyl diselenides, selenocarboxylates and cyclic selenoanhydrides

  摘要：

  几种酰基氯与 LiAlHSeH 反应合成了各种二酰基硒化物、二酰基二硒化物和硒羧酸盐。二酰氯与 LiAlHSeH 反应生成了环硒酸酐。在 77Se NMR 光谱中，我们发现二酰基硒化物和二酰基二硒化物的化学位移有助于区分它们。

  DOI：

  10.1039/b200147k

文献信息

• The Synthesis and Properties of Diacyl Selenides
  作者：Hideharu Ishihara、Shigeyuki Sato、Yoshio Hirabayashi

  DOI：10.1246/bcsj.50.3007

  日期：1977.11

  Diacyl selenides were synthesized in good yields by the deselenization of diacyl diselenides, which have conveniently been prepared from acyl chlorides and sodium hydroselenide. The reaction of dibenzoyl selenide with piperidine at 0 °C formed a fairly stable piperidinium salt. The methanolysis of distearoyl selenide gave selenostearic acid as an unstable intermediate.

  通过对二酰基二硒化物进行脱硒合成了二酰基硒化物，而二酰基二硒化物是从酰基氯和氢硒化钠中方便地制备出来的。二苯甲酰基硒化物与哌啶在 0 °C 下反应生成了相当稳定的哌啶盐。二硬脂酰硒化物的甲醇分解产生的硒硬脂酸是一种不稳定的中间体。
• SELENIUM TRANSFER REACTION OF PRIMARY SELENOAMIDES: A NOVEL METHOD FOR THE SYNTHESIS OF DIACYLSELENIDES FROM ACYL CHLORIDES
  作者：Hua-Rong Zhao、Xin-Jian Zhao、Xian Huang

  DOI：10.1081/scc-120014047

  日期：2002.1

  ABSTRACT Diacyl selenides were afford in excent yields by reaction of primary selenoamides with acyl chlorides in chloroform. A possible mechanism is discussed.

  摘要 通过伯硒酰胺与酰氯在氯仿中的反应，可以得到高产率的二酰基硒化物。讨论了一种可能的机制。
• Synthesis of seleno-fucose compounds and their application to the X-ray structural determination of carbohydrate-lectin complexes using single/multi-wavelength anomalous dispersion phasing
  作者：Junpei Shimabukuro、Hisayoshi Makyio、Tatsuya Suzuki、Yosuke Nishikawa、Masato Kawasaki、Akihiro Imamura、Hideharu Ishida、Hiromune Ando、Ryuichi Kato、Makoto Kiso

  DOI：10.1016/j.bmc.2016.12.021

  日期：2017.2

  Selenium-incorporated fucoses (seleno-fucoses) differing in the position of the seleno-substituent were synthesized and applied to the X-ray structural determination of a carbohydrate-lectin complex using single/multi-wavelength anomalous dispersion (SAD/MAD) phasing. The hydroxyl groups at the C-1, -2, -3 and -4 position of fucose were individually substituted with a methylseleno group via a transacetalization reaction using MeSeCH2OBn or by an S(N)2 reaction with TolSe-equivalents to afford the corresponding MeSe-fucose. The three-dimensional structures of a fucose-binding lectin complexed with several of these MeSe-fucoses have been determined by SAD/MAD phasing by utilizing the diffraction of selenium in the bound MeSe-fucoses. (C) 2016 Elsevier Ltd. All rights reserved.
• Expanded potential of seleno-carbohydrates as a molecular tool for X-ray structural determination of a carbohydrate–protein complex with single/multi-wavelength anomalous dispersion phasing
  作者：Tatsuya Suzuki、Hisayoshi Makyio、Hiromune Ando、Naoko Komura、Masanori Menjo、Yusuke Yamada、Akihiro Imamura、Hideharu Ishida、Soichi Wakatsuki、Ryuichi Kato、Makoto Kiso

  DOI：10.1016/j.bmc.2014.02.023

  日期：2014.4

  Seleno-lactoses have been successfully synthesized as candidates for mimicking carbohydrate ligands for human galectin-9 N-terminal carbohydrate recognition domain (NCRD). Selenium was introduced into the mono-or di-saccharides using p-methylselenobenzoic anhydride (Tol(2)Se) as a novel selenating reagent. The TolSe-substituted monosaccharides were converted into selenoglycosyl donors or acceptors, which were reacted with coupling partners to afford seleno-lactoses. The seleno-lactoses were converted to the target compounds. The structure of human galectin-9 NCRD co-crystallized with 6-MeSe-lactose was determined with single/multi-wavelength anomalous dispersion (SAD/MAD) phasing and was similar to that of the co-crystal with natural lactose. (C) 2014 Elsevier Ltd. All rights reserved.
• Reaction of Lithium Aluminum Hydride with Elemental Selenium:  Its Application as a Selenating Reagent into Organic Molecules
  作者：Hideharu Ishihara、Mamoru Koketsu、Yoshihisa Fukuta、Futoshi Nada

  DOI：10.1021/ja005800o

  日期：2001.8.1