5-isopropylidene-3-phenyl-2-thioxo-imidazolidin-4-one | 61632-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-isopropylidene-3-phenyl-2-thioxo-imidazolidin-4-one
• 英文别名: 5-Isopropyliden-3-phenyl-2-thioxo-imidazolidin-4-on；3-Phenyl-5-propan-2-ylidene-2-sulfanylideneimidazolidin-4-one
• CAS: 61632-47-1
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: BLFUXVGECQWZJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  254-257 °C (decomp)
• 沸点：
  331.8±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-isopropylidene-3-phenyl-2-thioxo-imidazolidin-4-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium hydride 作用下， 生成 5-isopropylidene-3-phenyl-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiohydantoin
  参考文献：
  名称：

  S-Glucosylated hydantoins as new antiviral agents

  摘要：

  S-Glycosylation took place on reaction of 5-alkylidene- and 5-arylidene-3-aryl-2-thiohydantoins with glycosyl halides under alkaline conditions. Bisglucosylation also took place when N-3 unsubstituted hydantoins were reacted. The bisglucosylated hydantoins produced N-3 glucosylated hydantoins on treatment with ammonia in methanol. In antiviral studies the most active compounds against both HSV-1 and HSV-2 were 5- (2-thienylmethylene) -3-phenyl-2-(2,3 4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl) -2- (2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin.

  DOI：

  10.1021/jm00027a009
• 作为产物：
  描述：

  2-anilino-5,5-dimethyl-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 生成 5-isopropylidene-3-phenyl-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  Cook et al., Journal of the Chemical Society, 1949, p. 2367,2369

  摘要：

  DOI：

文献信息

• Unprecedented One-Pot Chemocontrolled Entry to Thioxoimidazolidinones and Aminoimidazolones: Synthesis of Kinase Inhibitor Leucettamine B
  作者：Manikandan Selvaraju、Chung-Ming Sun

  DOI：10.1021/co500152s

  日期：2015.3.9

  A novel and highly chemoselective protocol for the construction of thioxoimidazolidinone and aminoimidazolone frameworks was explored, and the influence of the reaction conditions on product formation was studied to establish two distinct approaches for their selective formation. In this one-pot reaction, ambient temperature generally resulted in the formation of thioxoimidazolidinones, whereas microwave irradiation provided aminoimidazolones exclusively. An attempt to elucidate the observed chemoselectivity is described, and the products were confirmed by X-ray studies. One-pot synthesis toward Leucettamine B, a marine alkaloid, was achieved on the basis of this protocol.
• VOLKMANN R. A., SYNTH. COMMUN., 1978, 8, NO 8, 541-547
  作者：VOLKMANN R. A.

  DOI：——

  日期：——
• Cook et al., Journal of the Chemical Society, 1949, p. 2367,2369
  作者：Cook et al.

  DOI：——

  日期：——
• S-Glucosylated hydantoins as new antiviral agents
  作者：Ahmed A. El-Barbary、Ahmed I. Khodair、Erik B. Pedersen、Claus Nielsen

  DOI：10.1021/jm00027a009

  日期：1994.1

  S-Glycosylation took place on reaction of 5-alkylidene- and 5-arylidene-3-aryl-2-thiohydantoins with glycosyl halides under alkaline conditions. Bisglucosylation also took place when N-3 unsubstituted hydantoins were reacted. The bisglucosylated hydantoins produced N-3 glucosylated hydantoins on treatment with ammonia in methanol. In antiviral studies the most active compounds against both HSV-1 and HSV-2 were 5- (2-thienylmethylene) -3-phenyl-2-(2,3 4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl) -2- (2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin.