4,5-dihydrocanthin-6-one | 18122-85-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: 4,5-dihydrocanthin-6-one
• 英文别名: canthin-6-one；1,6-Diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16),10,12,14-hexaen-2-one；1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16),10,12,14-hexaen-2-one
• CAS: 18122-85-5
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: KXBQYMQMSNZAKO-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  372.0±34.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydrocanthin-6-one 在 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 42.0h， 生成 铁屎米酮N氧化物
  参考文献：
  名称：

  Canthin-6-one β-Carboline 系列中的溶液相和纳米颗粒生物合成启发的互连以及对 C 表型特性的研究。线虫

  摘要：

  基于来自色胺等简单前体的角蛋白-6-一生物碱的生物合成线，目前的工作重点是研究 Bischler-Napieralski 反应的替代方案，并全面覆盖了不同的生物合成中间体。纳米颗粒也被制备为生物合成装配线的模拟物，并且还报道了一些有趣的化学生态学生物学结果。

  DOI：

  10.1002/ejoc.201300770
• 作为产物：
  描述：

  1,2,3,3a,4,5-六氢铁屎米酮 在 manganese(IV) oxide 作用下， 以 甲苯 、 苯 为溶剂， 反应 60.0h， 以78%的产率得到4,5-dihydrocanthin-6-one
  参考文献：
  名称：

  An Improved Synthesis of Canthin-6-one

  摘要：

  An improved route has been devised which provides canthin-6-one in the highest yield from tryptamine to date. Tryptamine is converted to N-b-benzyltryptamine via reaction with benzoylchloride and reduction using LAH. Pictet-Spengler condensation with 2-ketoglutaric acid, removal of the protecting group by CTH, and aromatization with MnO2 affords canthin-6-one in 48% overall yield.

  DOI：

  10.1081/scc-120017199

文献信息

• Loss of THCCOOH from Urine Specimens Stored in Polypropylene and Polyethylene Containers at Different Temperatures
  作者：P. R. Stout、C. K. Horn、D. R. Lesser

  DOI：10.1093/jat/24.7.567

  日期：2000.10.1

  The loss of Δ9-tetrahydrocannabinol (THCCOOH) from urine specimens stored in polypropylene and polyethylene containers at 4°C and 25°C was examined. All specimens were analyzed by GC-MS after sampling at various times over a one-week period. Data were analyzed by one-way analysis of variance and fitted with a first order kinetic equation. Rapid loss of THCCOOH was seen at 4°C for both polypropylene (14% maximal loss, t½ = 0.53 min) and polyethylene (17% maximal loss, t½ = 5.77 min) bottles. At 25°C, a small loss (< 5%) was observed in polypropylene and no significant loss was seen for urine in polyethylene. All losses stabilized within 1 h, and no further losses were seen over one week. The results indicate that THCCOOH binding may be due to decreased solubility of THCCOOH at lower temperatures and subsequent association of THCCOOH with the more lipophilic plastic. The results also indicate that polypropylene and polyethylene do not bind THCCOOH to such an extent as to compromise the integrity of specimens.

  在4°C和25°C下，储存在聚丙烯和聚乙烯容器中的尿液样本中Δ9-四氢大麻酚（THCCOOH）的损失进行了研究。所有样本在一周内的不同时间点进行取样后通过气相色谱-质谱法（GC-MS）进行了分析。数据通过单因素方差分析进行分析，并拟合为一阶动力学方程。在4°C下，聚丙烯瓶的THCCOOH快速损失（最大损失14%，半衰期t½ = 0.53分钟），而聚乙烯瓶的损失也很快（最大损失17%，半衰期t½ = 5.77分钟）。在25°C下，聚丙烯瓶中观察到较小的损失（< 5%），而聚乙烯中的尿液没有显著损失。所有损失在1小时内稳定，且在一周内未见进一步损失。结果表明，THCCOOH结合可能是由于在较低温度下THCCOOH的溶解度降低，以及THCCOOH与更脂溶性的塑料的后续结合。结果还表明，聚丙烯和聚乙烯并没有以至于影响样本完整性的程度结合THCCOOH。
• Synthesis, in vitro antibacterial activities of a series of 3- N -substituted canthin-6-ones
  作者：Jiang-Kun Dai、Wen-Jia Dan、Na Li、Hong-Tao Du、Ji-Wen Zhang、Jun-Ru Wang

  DOI：10.1016/j.bmcl.2015.11.070

  日期：2016.1

  An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (mu g.mL(-1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (mu g.mL(-1)) against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Alkyl-Substituted Pyridines by Directed Pd(II)-Catalyzed C–H Activation of Alkanoic Amides
  作者：Thorsten Bach、Peng Hu

  DOI：10.1055/s-0035-1560810

  日期：——

  A general alkylation protocol for substituted iodopyridines was developed (32 examples, 44-97% yield). The reaction is based on the Pd(II)-catalyzed C-H activation of 8-aminoquinoline-derived alkanoic amides and it employs a catalyst cocktail of Pd(OAc)(2) (10 mol%), NaI (30 mol%), and (BuO)(2)POOH (20 mol%), with Ag2CO3 as base.
• Ohmoto, Taichi; Koike, Kazuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 1, p. 170 - 173
  作者：Ohmoto, Taichi、Koike, Kazuo

  DOI：——

  日期：——
• A study of the herb Aerva lanata. III. Alkaloids
  作者：G. G. Zapesochnaya、L. N. Pervykh、V. A. Kurkin

  DOI：10.1007/bf00630321

  日期：——