O-(2-bromo-5-methoxyphenyl) dimethylcarbamothioate | 115768-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: O-(2-bromo-5-methoxyphenyl) dimethylcarbamothioate
• 英文别名: O-(2-bromo-5-methoxyphenyl) N,N-dimethylcarbamothioate
• CAS: 115768-56-4
• 化学式: C₁₀H₁₂BrNO₂S
• 分子量: 290.181
• InChiKey: HOJSEQXJVQLNNN-UHFFFAOYSA-N

物化性质

• 沸点：
  333.0±52.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-(2-bromo-5-methoxyphenyl) dimethylcarbamothioate 在 titanium(IV) isopropylate 、 三乙基硅烷 、 叔丁基过氧化氢 、 氢氧化钾 、 正丁基锂 、 D-(-)-酒石酸二乙酯 、 potassium carbonate 、 三氟乙酸 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 224.5h， 生成 4-(4-methoxy-2-(S)-methylsulfinylphenyl)piperidine
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i
• 作为产物：
  描述：

  3-甲氧基苯酚 在 三乙烯二胺 、 溴 、 过氧化苯甲酰 作用下， 以 三氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 O-(2-bromo-5-methoxyphenyl) dimethylcarbamothioate
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i

文献信息

• A high temperature investigation using microwave synthesis for electronically and sterically disfavoured substrates of the Newman–Kwart rearrangement
  作者：Jonathan D. Moseley、Philip Lenden

  DOI：10.1016/j.tet.2007.02.101

  日期：2007.5

  Electronically deactivated and/or sterically hindered substrates undergo the Newman–Kwart rearrangement (NKR) at around 300 °C, beyond the range of most convenient and safe, small-scale laboratory equipment. We report here the convenient conversions of several difficult substrates using modern microwave technology, which has proven ideal for investigating this high temperature reaction in all but the most

  电子灭活和/或空间受阻的底物会在约300°C的温度下经受Newman-Kwart重排（NKR），这超出了最方便，最安全的小型实验室设备的范围。我们在这里报告了使用现代微波技术可以轻松转换几种困难的底物的方法，事实证明，除最难处理的情况之外，该方法对于研究这种高温反应是理想的选择。另外，重新研究了几个先前报道的困难实例，并且由于阐述的各种原因，发现在这些条件下不需要高温。
• A New Approach to Rapid Parallel Development of Four Neurokinin Antagonists. Part 4. Synthesis of ZD2249 Methoxy Sulfoxide
  作者：Sharon A. Bowden、J. Nigel Burke、Fiona Gray、Steven McKown、Jonathan D. Moseley、William O. Moss、Paul M. Murray、Matthew J. Welham、Maureen J. Young

  DOI：10.1021/op030039z

  日期：2004.1.1

  The manufacture of ZD2249 methoxy sulfoxide (1) using a new project approach is described. Research department processes were scaled up to 100 L if process safety and robustness were not compromised; other factors were treated according to the new approach. Using this strategy, we were able to manufacture a key intermediate on sufficient scale to support delivery of 1 kg quantities of bulk drug within

  描述了使用新的项目方法制造 ZD2249 甲氧基亚砜 (1)。如果过程安全性和稳健性不受影响，研究部门的过程可扩大到 100 L；其他因素按照新方法处理。使用这种策略，我们能够在实验室工作开始后的 6 个月内制造出足够规模的关键中间体，以支持交付 1 公斤的原料药。
• 2-Pyridinyl-phenyl-sulphinyl-and-phenyl-thio-benzimidazoles having
  申请人：Fisons plc

  公开号：US04900751A1

  公开（公告）日：1990-02-13

  Compounds of formula I, ##STR1## in which A is a 5 or 6 membered, fully unsaturated, carbocyclic or heterocyclic ring, B is a 5 or 6 membered, fully unsaturated, nitrogen containing heterocyclic ring, X is NR.sub.19, O or S, R.sub.19 is hydrogen or alkyl optionally substituted by --OCOR, n is 0 or 1, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 have various significances, R.sub.1 and R.sub.2, are hydrogen or alkyl or together with the ring carbon atoms to which they are attached, form a benzene or pyridine ring, which ring carries substituents R.sub.15, R.sub.16, R.sub.17 and R.sub.18, R.sub.15, R.sub.16, R.sub.17 and R.sub.18, have various significances, with certain provisos are described. Processes for making the compounds and pharmaceutical formulations containing them, e.g. for the treatment of conditions including excess gastric acid secretion, are also described.

  化合物的化学式为I，##STR1## 其中A是一个5或6成员的，完全不饱和的，碳环或杂环，B是一个5或6成员的，完全不饱和的，含氮的杂环，X是NR.sub.19，O或S，R.sub.19是氢或烷基，可以选择地被--OCOR取代，n为0或1，R.sub.3，R.sub.4，R.sub.5，R.sub.6，R.sub.7，R.sub.8，R.sub.9和R.sub.10具有不同的含义，R.sub.1和R.sub.2是氢或烷基，或者与它们连接的环碳原子一起形成苯或吡啶环，该环带有取代基R.sub.15，R.sub.16，R.sub.17和R.sub.18，R.sub.15，R.sub.16，R.sub.17和R.sub.18具有不同的含义，在特定条件下描述。还描述了制备这些化合物和含有它们的药物配方的方法，例如用于治疗包括胃酸过多等病症。
• Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates
  作者：Yutaka Matsuo、Yun Yu、Xiao-Yu Yang、Hiroshi Ueno、Hiroshi Okada、Hiromasa Shibuya、Yeong Suk Choi、Yong Wan Jin

  DOI：10.1021/acs.joc.9b00549

  日期：2019.5.17

  Benzothieno[60]fullerenes were synthesized using fullerenyl cations as key intermediates. The reaction proceeded through a nucleophilic attack of the sulfur atom as a weak nucleophile to the fullerenyl cation electrophile. A monoarylated fullerene, (2-methylthiophenyl)hydro[60]fullerene, C60ArH (Ar = C6H4-SMe-2 and so on; four derivatives) was subjected to deprotonation with KOtBu to form a fullerenyl

  苯并噻吩并[60]富勒烯是使用富勒烯阳离子作为关键中间体合成的。该反应通过作为弱亲核体的硫原子对富勒烯阳离子亲电体的亲核攻击而进行。将单芳基化的富勒烯，（2-甲基硫代苯基）氢[60]富勒烯，C 60 ArH（Ar = C 6 H 4 -SMe-2等；四种衍生物）用KO t Bu脱质子化以形成富勒烯基阴离子ArC 60 –，然后使用I 2氧化生成富勒烯阳离子ArC 60 +，通过富勒烯阳离子-S与产物的相互作用，导致分子内脱甲基环化。电化学和计算研究表明，由于稠合的噻吩基部分的HOMO相对较高，该化合物的带隙比通常的富勒烯衍生物略窄。
• FUSED BENZENE DERIVATIVE AND USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1553074B1

  公开（公告）日：2014-06-18