bis(N,N-dimethylcarbamoyl) diselenide | 36598-11-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: bis(N,N-dimethylcarbamoyl) diselenide
• 英文别名: Se-(dimethylcarbamoylselanyl) N,N-dimethylcarbamoselenoate
• CAS: 36598-11-5
• 化学式: C₆H₁₂N₂O₂Se₂
• 分子量: 302.093
• InChiKey: PWZBKVQMRSCFDX-UHFFFAOYSA-N

物化性质

• 熔点：
  102.0-103.0 °C (decomp)(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  316.8±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(N,N-dimethylcarbamoyl) diselenide 生成 Se-(dimethylcarbamoyl) N,N-dimethylcarbamoselenoate
  参考文献：
  名称：

  四烷基脲合成的新途径。一氧化碳与硒和二烷基胺的反应

  摘要：

  一氧化碳与硒和二烷基胺反应，然后在 0°C 下用分子氧氧化得到双（N，N-二烷基氨基甲酰基）二硒化物，热解得到双（N，N-二烷基氨基甲酰基）硒化物和四烷基脲。

  DOI：

  10.1246/cl.1972.401
• 作为产物：
  描述：

  dimethylammonium N,N'-dimethylmonoselenocarbamate 在 氧气 作用下， 生成 bis(N,N-dimethylcarbamoyl) diselenide
  参考文献：
  名称：

  四烷基脲合成的新途径。一氧化碳与硒和二烷基胺的反应

  摘要：

  一氧化碳与硒和二烷基胺反应，然后在 0°C 下用分子氧氧化得到双（N，N-二烷基氨基甲酰基）二硒化物，热解得到双（N，N-二烷基氨基甲酰基）硒化物和四烷基脲。

  DOI：

  10.1246/cl.1972.401

文献信息

• Novel generation of selenoaldehydes through stannic chloride-induced unsymmetrical C–Se bond cleavage of bis(N,N-dimethylcarbamoylseleno)methanes
  作者：Kazuaki Shimada、Yaling Gong、Hidenori Nakamura、Rei Matsumoto、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1016/j.tetlet.2005.03.153

  日期：2005.5

  Treatment of a benzene or a CH2Cl2 solution of bis(N,N-dimethylcarbamoylseleno)methanes with SnCl4 afforded β-1,3,5-triselenanes, and the key intermediates, acylselonium ions and selenoaldehydes, were successfully trapped by using allyltrimethylsilane or 2,3-dimethyl-1,3-butadiene to obtain the allylation products or the cycloadducts, respectively.

  用SnCl 4处理双（N，N-二甲基氨基甲酰基硒基）甲烷的苯或CH 2 Cl 2溶液可得到β-1,3,5-三硒烯，并成功地通过捕获了关键中间体酰基ls离子和硒醛烯丙基三甲基硅烷或2,3-二甲基-1,3-丁二烯分别获得烯丙基化产物或环加合物。
• Stannic chloride-induced unsymmetrical CSe bond cleavage of bis(N,N-dimethylcarbamoylseleno)methanes: Novel generation of selenoaldehydes
  作者：Yaling Gong、Kazuaki Shimada、Hidenori Nakamura、Masamichi Fujiyama、Akihiro Kodama、Miyuki Otsuki、Rei Matsumoto、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1002/hc.20190

  日期：——

  Treatment of bis(N,N-dimethylcar- bamoylseleno)methanes with SnCl4 afforded β-1,3,5-triselenanes in moderate to high yields, and the key intermediates of the reactions, i.e., acylselonium ions and selenoaldehydes, were successfully trapped by using allyltrimethylsilane or 2,3-dimethyl-1,3-butadiene to obtain the allylation products or the cycloadducts, respectively. © 2006 Wiley Periodicals, Inc. Heteroatom

  用 SnCl4 处理双（N,N-二甲基氨基甲酰硒）甲烷以中等至高产率获得 β-1,3,5-三硒烷，反应的关键中间体，即酰基硒离子和硒醛被成功捕获使用烯丙基三甲基硅烷或2,3-二甲基-1,3-丁二烯分别得到烯丙基化产物或环加合物。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:125–135, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20190
• A Preparation of Alkyl or Alkenyl<i>N</i>,<i>N</i>-Dimethylchalcogenocarbamates and Their One-Step Conversion into Symmetrical Dialkyl or Dialkenyl Dichalcogenides
  作者：Kazuaki Shimada、Seiji Oikawa、Hidenori Nakamura、Akiko Moro-oka、Miho Kikuchi、Akiko Maruyama、Takahiro Suzuki、Hisashi Kogawa、Yukiko Inoue、Yaling Gong、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1246/bcsj.78.899

  日期：2005.5

  Alkyl or alkenyl N,N-dimethylchalcogenocarbamates were easily prepared by a stepwise treatment of bis(N,N-dimethylcarbamoyl) dichalcogenides with NaH or NaBH4, followed by various alkylating agents or acetylenes bearing electron-withdrawing substituents. The one-step conversion of alkyl or alkenyl N,N-dimethylselenocarbamates or N,N-dimethyltellurocarbamates into the corresponding symmetrical dialkyl or dialkenyl dichalcogenides was also achieved efficiently by treating with SnCl4.

  先用 NaH 或 NaBH4 分步处理双（N,N-二甲基氨基甲酰基）二羰基化合物，再用各种烷基化剂或带有抽电子取代基的乙炔基，就能轻松制备出烷基或烯基 N,N-二甲基羰基氨基甲酸盐。用 SnCl4 处理烷基或烯基 N,N-二甲基硒羰基氨基甲酸酯或 N,N-二甲基碲羰基氨基甲酸酯，也能一步高效地转化为相应的对称二烷基或二烯基二羰基化合物。
• Synthesis of Isochalcogenazole Rings by Treating β-(<i>N</i>,<i>N</i>-Dimethylcarbamoylchalcogenenyl)alkenyl Ketones with Hydroxylamine-<i>O</i>-sulfonic Acid
  作者：Kazuaki Shimada、Akiko Moro-oka、Akiko Maruyama、Hiroyuki Fujisawa、Toshio Saito、Ryo Kawamura、Hisashi Kogawa、Maiko Sakuraba、Yukichi Takata、Shigenobu Aoyagi、Yuji Takikawa、Chizuko Kabuto

  DOI：10.1246/bcsj.80.567

  日期：2007.3.15

  β-(N,N-Dimethylcarbamoylselenenyl)- and β-(N,N-dimethylcarbamoyltellurenyl)alkenyl ketones were converted into isoselenazoles and isotellurazole Te-oxides, respectively, simply by treating with hydroxylamine-O-sulfonic acid, and deoxygenation of the latter products was successfully carried out by treating with PPh3. Alternative treatment of ynone oxime tosylates with hydrochalcogenide ions or N,N-dimethylchalcogenocarbamate ions also gave the same isochalcogenazole rings. These reactions were assumed to proceed through intramolecular nucleophilic substitution on the nitrogen atom of oxime sulfonates by the attack of in situ generated chalcogen nucleophiles.

  β-(N,N-二甲基氨基甲酰硒基)- 和 β-(N,N-二甲基氨基甲酰月桂酰)烯基酮只需用羟胺-O-磺酸处理，就能分别转化为异硒唑和异碲唑羰基化合物。用氢化钙离子或 N,N-二甲基钙镁离子处理炔酮肟对甲苯磺酸盐，也能得到相同的异钙唑环。假定这些反应是通过肟磺酸盐的氮原子受到原位生成的醛基亲核物的攻击而发生的分子内亲核取代反应。