2,3-dihydro-3,3-dimethylbenzo[b]thiophene | 14422-01-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-dihydro-3,3-dimethylbenzo[b]thiophene
• 英文别名: 3,3-dimethyl-2H-1-benzothiophene
• CAS: 14422-01-6
• 化学式: C₁₀H₁₂S
• 分子量: 164.271
• InChiKey: AWCLHCPLRBKVAV-UHFFFAOYSA-N

物化性质

• 沸点：
  56.3-58.2 °C(Press: 0.37 Torr)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-3,3-dimethylbenzo[b]thiophene 在 三氯化铝 作用下， 以 四氢呋喃 、 二硫化碳 为溶剂， 反应 6.0h， 生成 2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-but-3-en-2-ol
  参考文献：
  名称：

  Biologically Active Heteroarotinoids Exhibiting Anticancer Activity and Decreased Toxicity

  摘要：

  A series of retinoids, containing heteroatoms in a cyclic ring and called heteroarotinoids, were synthesized, and their biological activity was evaluated using tissue culture lines that have measurable responses to trans-retinoic acid (t-RA). Transglutaminase (TGase) was assessed in the human erythroleukemia cell line (GM06141A) as an indicator of differentiation and apoptosis. Proliferation was evaluated in a human cervical cell line, CC-1, which exhibits dose-dependent alterations in growth rate in response to treatment with trans-retinoic acid. Activation of nuclear retinoic acid receptors was determined in a reporter cell line established from CC-1. The reporter line, called CC-B, contains a reporter gene controlled by a retinoic acid responsive element (RARE) and a thymidine kinase (tk) promoter. Treatment of the CC-B line with the heteroarotinoids resulted in a dose-responsive and retinoid-dependent regulation of reporter gene expression. The heteroarotinoids exhibited activity in all assays and correlated in a statistically significant manner between assays. RARE transactivation activity in CC-B cells correlated with induction of TGase in GM06141A (R = 0.96) and with a decrease in the growth rate of CC-1 cells (R = -0.90). The ability of the selected heteroarotinoids to induce differentation, inhibit proliferation, and activate nuclear receptors demonstrates the chemotherapeutic potential of these agents. In view of the biological activity cited, an in vivo toxicity study was conducted on male B6D2F1 mice with three heteroarotinoids, namely 8 [(2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimethylthio- chroman-6-yl)-2,4,6-heptatrienoic acid], 10 [2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimethylchroman-6-yl)-2,4,6-heptatrienoic acid], and 13 [(E)-p-[2-(4,4-dimethylchroman-6-yl)propenyl]benzoic acid]. The mice were used with gavage of heteroarotinoids in corn oil [0.1, 0.2, 0.4, or 0.8 mg/kg] and with 0.01 or 0.05 mg/kg of TTNPB (5) [(E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid] as reference controls. The target organs affected in the mice by the three heteroarotinoids were those typically associated with t-RA (1) toxicity. The maximum tolerated dose (MTD) of 13 was 9.4 mg/kg/day, which was equal in toxicity to that of t-RA (1) and 1000-fold less toxic than TTNPB (5). The MTDs of 8 and 10 were 34 and 32 mg/kg/day, respectively, which is 3-fold less toxic than t-RA (1) and 3000-fold less toxic than TTNPB (5). The 3000-fold reduced toxicity, compared with only a 27% reduction biological activity of 8 and 10 with respect to that of TTNPB, observed in our assays indicates a good therapeutic ratio of these heteroarotinoids over the parent compound. The biological activity and reduced toxicity of these heteroarotinoids demonstrate the potential efficacy as anticancer agents.

  DOI：

  10.1021/jm970196m
• 作为产物：
  描述：

  2-methyl-1-(phenylthio)propan-2-ol 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 3.0h， 以80.5%的产率得到2,3-dihydro-3,3-dimethylbenzo[b]thiophene
  参考文献：
  名称：

  新型杂芳类化合物：合成和生物活性。

  摘要：

  在这项研究中，合成了13种杂芳类化合物。每种制备方法中的关键步骤是适当的苯并噻吩基，苯并噻吩基取代的苯并二氢吡喃取代的磷叶立德与相应的nium盐的独立合成得到的缩合，与所选的多烯取代的醛酯缩合。这些杂环中的九个包含硫代苯并二氢吡喃基团，两个具有苯并二氢吡喃基团，另外两个具有苯并噻吩基系统。用两种测定法之一筛选化合物。一种测定法测定了类维生素A抑制佛波酯诱导的小鼠表皮鸟氨酸脱羧酶（ODC）活性增加的能力。另一种测定法测定了类维生素A诱导的人肌样白血病细胞系HL-60的分化。在ODC分析中，筛选了所有13种化合物。活性最高的杂芳烃类化合物是酯10 [甲基（E）-4- [2-（2,2,4,4-四甲基硫代苯并吡喃-6-基）-1-丙烯基]苯甲酸酯]和酸11 [（E）-4- [2-（2,2,4,4-四甲基-3,4-二氢-2H-1-苯并噻喃-6-基）-1-丙烯基]苯甲酸]。这两种类维生素A的ID50值（

  DOI：

  10.1021/jm00105a065

文献信息

• Free radical chemistry of nucleosides and nucleotides. Ring opening of C4′-radicals
  作者：David Crich、Qingwei Yao

  DOI：10.1016/s0040-4020(97)10262-9

  日期：1998.1

  It is demonstrated that nucleotide C4′ radicals may be generated from a C4′-thiolester on treatment with tributyltin hydride. When the reaction is conducted in benzene at reflux the C4′ radical expels the C3′-phosphate group to give a radical cation. This species undergoes deprotonation to an allylic radical which suffers cleavage of the deoxyribose ring. Similar reactions are observed when the reaction

  已经证明，在用氢化三丁基锡处理时，可以从C4'-硫代酸酯产生核苷酸C4'基团。当反应在苯中在回流条件下进行时，C4'自由基将C3'-磷酸基团排出，得到自由基阳离子。该种类经历去质子化为烯丙基自由基，该烯丙基自由基遭受脱氧核糖环的裂解。当用三（三甲基甲硅烷基）硅烷代替锡烷进行反应时，观察到类似的反应。在甲醇苯中，自由基阳离子被甲醇捕获，得到一个新的C4'自由基，该自由基在开环之前被淬灭。根据C3'处的取代基所施加的构象，讨论了C4'自由基对开环的行为。
• Ring expansion or spirocyclisation of (phenylthiomethylene)cycloalkanes with aluminium chloride viaβ-thio carbocations
  作者：Daphné Derouane、Jeremy N. Harvey、Heinz G. Viehe

  DOI：10.1039/c39950000993

  日期：——

  The title reactions can be explained by Wagner–Meerwein rearrangement of α-thio carbocations (thionium ions) to β-thio carbocations; this unusual reactivity may be due to superelectrophilic activation by aluminium chloride.

  标题反应可以用δ-硫代碳基（噻吩离子）到δ-硫代碳基的瓦格纳-梅尔韦恩重排来解释；这种不寻常的反应性可能是由于氯化铝的超亲电活化作用。
• Ligand-field transition-induced C–S bond formation from nickelacycles
  作者：Jeongcheol Shin、Jiseon Lee、Jong-Min Suh、Kiyoung Park

  DOI：10.1039/d1sc05113j

  日期：——

  that govern the photoactivity of organonickel complexes have not yet been established. Here we report the excited-state cross-coupling activities of Ni(II) metallacycle compounds, which display ∼104 times enhancement for the C–S bond-forming reductive elimination reaction upon Ni-centered ligand-field transitions. The effects of excitation energy and ancillary ligands on photoactivity have been investigated

  光激发是公认的激活镍基交叉偶联反应的方法之一，但控制有机镍配合物光活性的因素尚未确定。在这里，我们报道了Ni（ II ）金属环化合物的激发态交叉偶联活性，该化合物在以Ni为中心的配体场跃迁时，对C-S键形成还原消除反应表现出〜10 4倍的增强。使用 17 种不同的镍环物质与四种相应的无环配合物结合，研究了激发能和辅助配体对光活性的影响。光谱和计算电子结构表征表明，无论配位物种如何，d-d转变都可以引起Ni-C键均裂，并且所得Ni()物种的反应性决定了整个反应的产物。本研究中建立的光活性机制为有机镍（ II ）配合物的激发态化学提供了一般性的见解。
• PHENYL SULFONAMIDES AS MODULATORS OF ION CHANNELS
  申请人：Martinborough Esther

  公开号：US20110082117A1

  公开（公告）日：2011-04-07

  The present invention relates to heterocyclic derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及杂环衍生物，可用作离子通道抑制剂。本发明还提供了包含本发明化合物的药学上可接受的组合物，并提供了使用这些组合物治疗各种疾病的方法。
• Sulfur-Atom Transfer from Elemental Sulfur to Nickel−Carbon Bonds as a New Route to Reactive Nickel(II) Thiolates
  作者：Runyu Han、Gregory L. Hillhouse

  DOI：10.1021/ja981266x

  日期：1998.8.1