(±)-trans-2,6-di(p-anisyl)tetrahydrothiopyran-4-one | 2573-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (±)-trans-2,6-di(p-anisyl)tetrahydrothiopyran-4-one
• 英文别名: (2S,6S)-2,6-bis(4-methoxyphenyl)thian-4-one
• CAS: 2573-84-4；68226-73-3；70071-29-3
• 化学式: C₁₉H₂₀O₃S
• 分子量: 328.432
• InChiKey: ICRGSDQNZOTTTN-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (±)-trans-2,6-di(p-anisyl)tetrahydrothiopyran-4-one 在 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cis-2,6-bis(4-methoxyphenyl)tetrahydro-4H-thiopyran-4-one-1,1-dioxide
  参考文献：
  名称：

  2,6-二芳基-4H-四氢-噻喃-4-酮 S-氧化物的化学选择性合成和抗动质体特性：它们在二亚芳基丙酮氧化还原反应级联中的相互作用

  摘要：

  2,6-二芳基-4H-四氢-噻喃-4-酮和相应的亚砜和砜衍生物被设计为通过前药作用降低其母体抗动铂二亚芳基丙酮的主要毒性。从二亚芳基丙酮和2,6-二芳基-4H-四氢-噻喃-4-酮中开发并推广了新的非对映选择性方法，以允许引入广泛的取代谱并制备相关的S-氧化物。评估了二亚芳基丙酮、2,6-二芳基-4H-四氢-噻喃-4-酮及其 S-亚砜和砜代谢物对布氏锥虫、克氏锥虫和各种利什曼原虫的体外生物活性和选择性。及其针对人成纤维细胞 hMRC-5 的细胞毒性。数据显示，迈克尔受体位点暂时被掩盖的硫化物、亚砜和砜对哺乳动物细胞的毒性较小，而对布氏锥虫、克氏锥虫、婴儿乳杆菌和锥虫的抗锥虫效力得以维持。 L. donovani，从而证实了前药策略的有效性。其作用机制被认为是由于二亚芳基丙酮参与涉及锥硫酮系统的级联氧化还原反应。迈克尔将二硫醇加成到双键上，形成伸长的聚合物，后者在 S-氧化后，随后进行顺式消除

  DOI：

  10.3390/molecules29071620
• 作为产物：
  描述：

  (1E,4e)-1,5-双(4-甲氧基苯基)-1,4-戊二烯-3-酮 在 sodium hydrosulfide hydrate 、 aliquant 336 作用下， 以 甲基叔丁基醚 为溶剂， 反应 18.0h， 以76%的产率得到(±)-trans-2,6-di(p-anisyl)tetrahydrothiopyran-4-one
  参考文献：
  名称：

  相转移催化非对映选择性合成 2,6-二芳基四氢噻喃-4-酮

  摘要：

  已经开发了两种有效的相转移催化方案，用于非对映选择性合成 2,6-二芳基四氢噻喃-4-酮 (2,6-DATHTPs) 的顺式和反式异构体。在对反应范围的研究中，不同取代的 2,6-DATHTP 在实验和制备规模上均以高产率和非对映体过量成功获得。

  DOI：

  10.1002/ejoc.201403516

文献信息

• COMPOUNDS USEFUL AGAINST KINETOPLASTIDEAE PARASITES
  申请人：Davioud-Charvet Elisabeth

  公开号：US20120214996A1

  公开（公告）日：2012-08-23

  Dibenzylidene and heterobenzylideneacetone derivatives, related 4-piperidones, related 4-thiopyranones and the corresponding sulfinyl- and sulfonyl-analogues for their use for prophylaxis or treatment of trypanosomiasis and leishmaniasis.

  二苄基亚烷和杂二苄基亚烷乙酮衍生物，相关的4-哌啶酮，相关的4-噻opyranones以及相应的亚磺酰基和磺酰基类似物，用于预防或治疗锥虫病和利什曼病。
• Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
  作者：Paramasivam Parthiban、Gopalakrishnan Aridoss、Paramasivam Rathika、Venkatachalam Ramkumar、Senthamaraikannan Kabilan

  DOI：10.1016/j.bmcl.2009.04.038

  日期：2009.6

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Spectral characterization and crystal structure of some 2,6-diarylthian-4-one hydrazone derivatives
  作者：C. Sankar、S. Umamatheswari、K. Pandiarajan

  DOI：10.1016/j.molstruc.2014.07.080

  日期：2014.11

  A series of cis and trans 2,6-diarylthian-4-one hydrazone derivatives (11-16) have been synthesized and characterized by H-1, C-13 and two dimensional NMR spectroscopy. For the 2r,6t-diphenylthian-4-one N-isonicotinoylhydrazone (14) X-ray diffraction have also been recorded. The coupling constants suggested that the cis-hydrazones (11-13), which have the phenyl groups in cis orientation, largely exist in chair conformations with equatorial orientation of the phenyl groups 11C. Analysis of the vicinal coupling constants of trans-hydrazones (14-16) suggests that boat forms 14B must make significant contributions to it and the relative population is 58%. Moreover, in solution chair conformations 14C and 14C', may contribute to 14. The NOESY and X-ray diffraction of 14 gives definite evidence for the contribution of 14C. (C) 2014 Elsevier B.V. All rights reserved.
• Nanjappan, Palaniappan; Ramalingam, Kondareddiar; Ramarajan, Krishnasamy, Phosphorus and Sulfur and the Related Elements, 1983, vol. 17, p. 331 - 342
  作者：Nanjappan, Palaniappan、Ramalingam, Kondareddiar、Ramarajan, Krishnasamy、Berlin, K. Darrell

  DOI：——

  日期：——
• US9174960B2
  申请人：——

  公开号：US9174960B2

  公开（公告）日：2015-11-03