benzhydryl isoselenocyanate | 27761-38-2

• 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: benzhydryl isoselenocyanate
• CAS: 27761-38-2
• 化学式: C₁₄H₁₁NSe
• 分子量: 272.208
• InChiKey: XTJGBGPOHHUOJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  benzhydryl isoselenocyanate 、 5-氨基-1H-咪唑-4-甲腈 在 吡啶 作用下， 反应 6.0h， 以41%的产率得到6,9-dihydro-2-benzhydrylamino-6-(3-benzhydrylureido)imino-1-selenapurine
  参考文献：
  名称：

  Synthesis of New 1-Chalcogenapurines by the Reaction of 5-Aminoimidazole-4-carbonitrile with Isochalcogenocyanates

  摘要：

  1-Chalcogenapurines[1-thiapurine derivatives (6,12c,d) and 1-selenapurine derivative (15)] and 1-substituted 1,6-dihydro-6-imino-9H-purine-2(3H)-chalcogenone (4a,b, 13) were synthesized by the reaction of 5(4)-aminoimidazole-4(5)-carbonitrile(3)with various isochalcogenocyanates in pyridine. The reaction of 3 with methyl isothiocyanate in pyridine afforded on ly the 1,6-dihydro-1-methyl-6-imino-9H-purine-2(3H)-thione (4a). On the other hand, the reactions of 3 with ethoxycarbonyl isothiocyanate, benzoyl isothiocyanate or benzhydryl isoselenocyanate preferentially gave the 1-chalcogenapurine derivatives (12c,d, 15), In turn, both 1,6-dihydro-1-phenyl-6-imino-9H-purine-2(3H)-thione (4b) and 6,9-dihydro-2-phenylamino-6-(3-phenylthioureido)imino-1-thiapurine (6) were produced by the reaction of 3 with phenyl isothiocyanate. Modes of cyclization reactions involving 3 and isochalcogenocyanate (R-N=C=X, X; S,Se) depend in remarkable extent on the chalcogene atom as well as R portion of R-N=C=X.

  DOI：

  10.3987/com-94-6871

文献信息

• Synthesis of 1,3-selenazoles and 2-imidazolin-5-selones from isoselenocyanates and isocyanides
  作者：Hajime Maeda、Nobuaki Kambe、Noboru Sonoda、Shin-ichi Fujiwara、Tsutomu Shin-ike

  DOI：10.1016/s0040-4020(97)00931-9

  日期：1997.10

  1,3-Selenazoles and 2-imidazolin-5-selones were synthesized by the reaction of isoselenocyanates (1) with alpha-lithiated isocyanides (11). Isocyanides having only one substituent at the alpha-carbon such as ethyl isocyanoacetate and benzyl isocyanide gave 1,3-selenazoles (9) in good yields. On the other hand, alpha,alpha-disubstituted isocyanides such as alpha-methylbenzyl isocyanide and diphenylmethyl isocyanide afforded 2-butylseleno-2-imidazolin-5-selones (18) after trapping with butyl iodide. The latter products were formed from one molecule of isocyanides and two molecules of isoselenocyanates. Plausible reaction pathways are proposed. (C) 1997 Elsevier Science Ltd.
• Synthesis of New 1-Chalcogenapurines by the Reaction of 5-Aminoimidazole-4-carbonitrile with Isochalcogenocyanates
  作者：Hiroatsu Matsumoto、Sumiko Hara、Nobuyuki Nagata、Kazuyoshi Ikeda、Yoshihisa Mizuno

  DOI：10.3987/com-94-6871

  日期：——

  1-Chalcogenapurines[1-thiapurine derivatives (6,12c,d) and 1-selenapurine derivative (15)] and 1-substituted 1,6-dihydro-6-imino-9H-purine-2(3H)-chalcogenone (4a,b, 13) were synthesized by the reaction of 5(4)-aminoimidazole-4(5)-carbonitrile(3)with various isochalcogenocyanates in pyridine. The reaction of 3 with methyl isothiocyanate in pyridine afforded on ly the 1,6-dihydro-1-methyl-6-imino-9H-purine-2(3H)-thione (4a). On the other hand, the reactions of 3 with ethoxycarbonyl isothiocyanate, benzoyl isothiocyanate or benzhydryl isoselenocyanate preferentially gave the 1-chalcogenapurine derivatives (12c,d, 15), In turn, both 1,6-dihydro-1-phenyl-6-imino-9H-purine-2(3H)-thione (4b) and 6,9-dihydro-2-phenylamino-6-(3-phenylthioureido)imino-1-thiapurine (6) were produced by the reaction of 3 with phenyl isothiocyanate. Modes of cyclization reactions involving 3 and isochalcogenocyanate (R-N=C=X, X; S,Se) depend in remarkable extent on the chalcogene atom as well as R portion of R-N=C=X.