bis(2-naphthylmethyl)disulfide | 165072-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(2-naphthylmethyl)disulfide
• 英文别名: 2-naphthylmethyl disulfide；1,2-bis(naphthalen-2-ylmethyl)disulfane；2,2'-[Disulfanediylbis(methylene)]dinaphthalene；2-[(naphthalen-2-ylmethyldisulfanyl)methyl]naphthalene
• CAS: 165072-40-2
• 化学式: C₂₂H₁₈S₂
• 分子量: 346.517
• InChiKey: NHYGIEOAQYXEIP-UHFFFAOYSA-N

物化性质

• 沸点：
  538.7±39.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(2-naphthylmethyl)disulfide 在 盐酸 、 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 3-Naphthalen-2-yl-2-(naphthalen-2-ylmethylsulfanyl)-propionic acid methyl ester
  参考文献：
  名称：

  Searching for Minimum Increments of Hydrophobic Collapse: Flexible Dinaphthyl Carboxylates

  摘要：

  In an effort to identify minimal units of hydrophobically induced folding, we have examined flexible molecules containing two naphthyl moieties connected by a four-atom linker that also bears a carboxyl group. Crystallographic data show that the linkers allow intramolecular edge-to-face association of the naphthyl groups without excessive strain in the backbone. For the carboxylate forms of the dinaphthyl compounds, the occurrence of intramolecular naphthyl-naphthyl proximity in aqueous solution (24 degrees C) was detected via upfield shifts in the aromatic region H-1 NMR signals, relative to mononaphthyl control compounds. The naphthyl-naphthyl proximity does not appear to be strongly ''hydrophobically driven'', however, because similar upfield shifts (dinaphthyl vs mononaphthyl carboxylates) were observed in 8 M aqueous urea, and for the corresponding carboxylic acids in CDCl3 and C6D6. We conclude that these upfield shifts largely reflect chance encounters between the naphthyl groups resulting from random conformational motion.

  DOI：

  10.1021/ja00129a014
• 作为产物：
  描述：

  naphthalen-2-ylmethyl carbamimidothioate monohydrobromide 在 sodium hydroxide 、 碘 作用下， 生成 bis(2-naphthylmethyl)disulfide
  参考文献：
  名称：

  Searching for Minimum Increments of Hydrophobic Collapse: Flexible Dinaphthyl Carboxylates

  摘要：

  In an effort to identify minimal units of hydrophobically induced folding, we have examined flexible molecules containing two naphthyl moieties connected by a four-atom linker that also bears a carboxyl group. Crystallographic data show that the linkers allow intramolecular edge-to-face association of the naphthyl groups without excessive strain in the backbone. For the carboxylate forms of the dinaphthyl compounds, the occurrence of intramolecular naphthyl-naphthyl proximity in aqueous solution (24 degrees C) was detected via upfield shifts in the aromatic region H-1 NMR signals, relative to mononaphthyl control compounds. The naphthyl-naphthyl proximity does not appear to be strongly ''hydrophobically driven'', however, because similar upfield shifts (dinaphthyl vs mononaphthyl carboxylates) were observed in 8 M aqueous urea, and for the corresponding carboxylic acids in CDCl3 and C6D6. We conclude that these upfield shifts largely reflect chance encounters between the naphthyl groups resulting from random conformational motion.

  DOI：

  10.1021/ja00129a014

文献信息

• Nanolayered cobalt–molybdenum sulphides (Co–Mo–S) catalyse borrowing hydrogen C–S bond formation reactions of thiols or H₂S with alcohols
  作者：Iván Sorribes、Avelino Corma

  DOI：10.1039/c8sc05782f

  日期：——

  Nanolayered cobalt–molybdenum sulphide (Co–Mo–S) materials have been established as excellent catalysts for C–S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds,

  纳米层硫化钴钼（Co-Mo-S）材料已被确定为 C-S 键构建的优异催化剂。这些催化剂可以用结构多样的硫醇和容易获得的伯醇和仲醇以良好至优异的产率制备各种硫醚。已证明在双键、腈、羧酸酯和卤素等敏感基团存在下的化学选择性。研究还表明，该反应是通过氢自转移（借氢）机制发生的，其中涉及 Co-Mo-S 介导的脱氢和氢化反应。使用这些地球上储量丰富的金属硫化物催化剂，还开发了一种基于醇与硫化氢 (H 2 S) 硫醚化以提供对称硫醚的新型催化方案。
• Natural product inspired allicin analogs as novel anti-cancer agents
  作者：Ishani Bhaumik、Kunal Pal、Utsab Debnath、Parimal Karmakar、Kuladip Jana、Anup Kumar Misra

  DOI：10.1016/j.bioorg.2019.01.057

  日期：2019.5

  nontoxic to the normal cells. Based on the LD50 values and selectivity index (SI), compound 3h (S-p-methoxybenzyl (p-methoxyphenyl)methanesulfinothioate) was considered as most promising anticancer agent amongst the above three compounds. Further bio-chemical studies confirmed that compound 3h promotes ROS generation, changes in mitochondrial permeability transition and induced caspase mediated DNA

  以高收率合成了大蒜中存在的一系列大蒜素的新类似物（S-烯丙基丙-2-烯-1-磺基硫代乙酸盐）。针对不同的乳腺癌细胞（MDA-MB-468和MCF-7）和非癌细胞（WI38）评估了合成的23种化合物。四种化合物（3f，3h，3m和3u）对癌细胞具有明显的细胞毒性，而对正常细胞无毒性。基于LD 50值和选择性指数（SI），化合物3h（Sp-甲氧基苄基（对甲氧基苯基）甲亚磺酸硫酯）被认为是上述三种化合物中最有希望的抗癌剂。进一步的生化研究证实，化合物3h促进ROS的产生，线粒体通透性转变的变化并诱导caspase介导的DNA损伤和凋亡。
• Trisulfides over disulfides: highly selective synthetic strategies, anti-proliferative activities and sustained H₂S release profiles
  作者：Debojit Bhattacherjee、Abu Sufian、Sulendar K. Mahato、Samiyara Begum、Kaustav Banerjee、Sharmistha De、Hemant Kumar Srivastava、Krishna P. Bhabak

  DOI：10.1039/c9cc05562b

  日期：——

  Temperature- and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.

  证明了温度和溶剂诱导的三硫化物和二硫化物的选择性合成。使用Na 2 S作为硫转移剂，可在温和，绿色，无催化剂和无添加剂的条件下实现显着的选择性。这项研究表明，对于持续释放H 2 S和有效的抗癌活性，三硫化物通常比二硫化物更好。
• A Facile Method for the Syntheses of Dialkyl Disulfides from Sulfur Under Phase Transfer Conditions
  作者：Jin-Xian Wang、Chin-Hsien Wang、Wenfeng Cui、Yulai Hu

  DOI：10.1080/00397919508015492

  日期：1995.11

  Abstract A convenient reaction of alkyl halides with sulfur in alkaline medium has been found to afford disulfides in good to excellent isolated yield under phase transfer conditions.

  摘要 已发现烷基卤化物与硫在碱性介质中的方便反应可在相转移条件下以良好至极好的分离产率提供二硫化物。
• A RAPID AND EFFICIENT SYNTHESIS OF SYMMETRICAL DISULFIDES UNDER MICROWAVE IRRADIATION CONDITIONS
  作者：Jin-Xian Wang、Lijuan Gao、Danfeng Huang

  DOI：10.1081/scc-120003143

  日期：2002.1

  ABSTRACT A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.

  摘要 合成对称二硫化物的一种快速而通用的方法包括硫与氢氧化钠在 PTC 微波辐射条件下反应得到二硫化钠，二硫化钠与卤代烷反应得到二硫化物，分离产率良好至极好。