2-溴-1,2-双(4-甲基苯基)乙酮 | 57297-30-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-溴-1,2-双(4-甲基苯基)乙酮
• 英文名称: 2-bromo-1,2-bis(4-methylphenyl)ethanone
• 英文别名: 2-bromo-1,2-bis(p-tolyl)ethanone；α-bromo-4,4'-dimethyl-deoxybenzoin；α-Brom-4,4'-dimethyl-desoxybenzoin
• CAS: 57297-30-0
• 化学式: C₁₆H₁₅BrO
• 分子量: 303.198
• InChiKey: XAJMXHOITUWTHR-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  383.4±32.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氨基-2-噻唑啉 、 2-溴-1,2-双(4-甲基苯基)乙酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以21%的产率得到3,4-di-p-tolyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents

  摘要：

  A series of substituted 5,6-diaryl-2,3-dihydroimidazo[2,1-b]thiazoles were synthesized and evaluated in the rat adjuvant-induced arthritis and mouse oxazolone-induced contact sensitivity assays to determine the potential of these compounds for use as immunoregulatory antiinflammatory agents. This class of compounds was derived by combining salient structural features of the antiinflammatory agent flumizole and the immunoregulatory drug levamisole. Unlike the latter two, a number of compounds in the target series were found to possess the desired combination of activities. Exploration of structure-activity relationships in the adjuvant-induced arthritic rat assay revealed that optimal potency was exhibited by symmetrically substituted 5,6-diaryl compounds having one of the following alkyl heteroatom or halogen functions at the para position: methoxy, ethoxy, methylthio, N-ethyl-N-methylamino, fluoro, or chloro. Scrambling of these two substituent classes to yield the asymmetrically substituted 5,6-diaryl compounds resulted in potent activity only with the 5-alkyl heteroatom, 6-halo-substituted regioisomers. However in the oxazolone-induced contact sensitivity assay, no consistent relationship of variation in activity with structural change was apparent. The initial target compound 5,6-bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole (1) was compared with its progenitors in additional models of inflammation and immunoregulation.

  DOI：

  10.1021/jm00147a008
• 作为产物：
  描述：

  1,2-di-p-tolyl-ethanone 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 以91%的产率得到2-溴-1,2-双(4-甲基苯基)乙酮
  参考文献：
  名称：

  靶向蝶啶还原酶 1 的抗寄生虫吡咯并嘧啶的基于结构的设计与合成

  摘要：

  非洲人类锥虫病的治疗仍然是撒哈拉以南非洲地区未满足的主要健康需求。涉及新分子目标的方法很重要；蝶啶还原酶 1 (PTR1) 是一种在锥虫属中减少二氢生物蝶呤的酶，已被确定为候选靶标，之前已表明取代的吡咯并 [2,3- d ] 嘧啶是布氏锥虫PTR1 的抑制剂( J. Med. Chem. 2010 , 53 , 221–229)。在本研究中，61 个新的吡咯并 [2,3- d]嘧啶已经制备，设计了 23 种与 PTR1 复合的化合物的新晶体结构，并在屏幕上评估了对 PTR1 的酶抑制活性和体外抗锥虫活性。八种化合物在两个筛选中都具有足够的活性，可以进行体内评估。因此，尽管获得了小鼠 I 期疾病模型中锥虫杀灭活性的证据，但这些化合物对小鼠的毒性太大，无法进一步开发。

  DOI：

  10.1021/jm500483b

文献信息

• An Expeditious One-Pot Synthesis of Thiiranes from α-Halo Ketones in Solvent­-Free Conditions Using Microwaves
  作者：Lal Dhar Yadav、Ritu Kapoor

  DOI：10.1055/s-2002-35222

  日期：——

  Thiiranes are obtained in excellent yields and with high diastereoselectivity upon microwave irradiation of a mixture of α-haloketones, O,O-diethyl hydrogen phosphorodithioate and alumina-supported sodium borohydride in solvent-free conditions.

  在无溶剂条件下，将α-卤代酮、O,O-二乙基氢膦双硫代酸酯和氧化铝负载的硼氢化钠混合物进行微波辐照，可以高产率和高对映选择性地合成噻丙烷。
• ORGANOPHOSPHOROUS CHEMISTRY: SELECTIVE TRANSFORMATION OF BENZOIN TO BENZIL, DESYL BROMIDE, OR BENZYL PHENYL KETONE
  作者：Isao Furukawa、Mitsuhiro Sasaki、Takeshi Inoue、Tetsuo Ohta

  DOI：10.1080/10426509808045488

  日期：1998.12.1

  converted to benzyl phenyl ketone via the Perkow reaction, and benzil was formed by the oxidation of benzoin by bromine. When triethylamine or triphenylphosphine was used as an added base, these bases trapped free bromine, and the oxidation product, benzil, was formed in low yield. In the presence of triphenylphosphine as a base, the Perkow reaction of desyl bromide proceeded smoothly to give benzyl phenyl

  摘要 安息香与二溴三苯基正膦在各种条件下的反应已得到深入研究。通过在三乙胺存在下用二溴三苯基正膦处理，苯偶姻被选择性地转化为脱磺酰溴，而在过量三苯基膦存在下形成苄基苯基酮。另一方面，仅用溴处理，安息香有效地被氧化而弯曲。还提出了产生这些的机制。Desyl bromide 由安息香与二溴三苯基正膦作为主要产物反应形成，并通过 Perkow 反应转化为苄基苯基酮，苯偶姻由溴氧化安息香形成。当使用三乙胺或三苯基膦作为添加的碱时，这些碱会捕获游离溴，氧化产物苯甲醇、以低产率形成。在三苯基膦作为碱存在下，脱乙酰溴的Perkow反应顺利进行，得到苄基苯基酮...
• Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation
  作者：Mahesh Shidore、Jatin Machhi、Kaushik Shingala、Prashant Murumkar、Mayank Kumar Sharma、Neetesh Agrawal、Ashutosh Tripathi、Zalak Parikh、Prakash Pillai、Mange Ram Yadav

  DOI：10.1021/acs.jmedchem.6b00426

  日期：2016.6.23

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.
• SHIMOKAWA NORIAKI; NAKAMURA HIDEO; SHIMAKAWA KEIKO; MINAMI HIDEO; NISHIMU+, J. MED. CHEM., 1979, 22, NO 1, 58-63
  作者：SHIMOKAWA NORIAKI、 NAKAMURA HIDEO、 SHIMAKAWA KEIKO、 MINAMI HIDEO、 NISHIMU+

  DOI：——

  日期：——
• MOROZOV, A. A., ZH. ORGAN. XIMII, 24,(1988) N 6, 1264-1270
  作者：MOROZOV, A. A.

  DOI：——

  日期：——