1,1-dibromo-2-(2-methoxyphenyl)ethene | 90585-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1-dibromo-2-(2-methoxyphenyl)ethene
• 英文别名: 1-(2,2-dibromovinyl)-2-methoxybenzene；2-Methoxy-beta,beta-dibromostyrene；1-(2,2-dibromoethenyl)-2-methoxybenzene
• CAS: 90585-32-3
• 化学式: C₉H₈Br₂O
• 分子量: 291.97
• InChiKey: NFAKVKGWPCPOLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dibromo-2-(2-methoxyphenyl)ethene 在 正丁基锂 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,3-苯并呋喃
  参考文献：
  名称：

  Electrophilic Reactions of Carbenoids. Synthesis of Fused Heterocyclic Systems via Intramolecular Nucleophilic Substitution of Carbenoids

  摘要：

  Intramolecular nucleophilic substitution of carbenoids with oxygen, nitrogen, and sulfur nucleophiles leading to the synthesis of fused heterocyclic compounds has been studied. For the purpose of this investigation styryl type gem-dihalides 4, 8, 18, 20, 28 containing a nucleophilic substituent in the ortho position of the aromatic ring have been synthesized. Carbenoids have been generated in those systems by the halogen-metal exchange reaction and shown to readily undergo intramolecular nucleophilic substitution by the properly located nucleophilic group (OH, SH, or NH2). As a result a new synthetic route to benzofurans, thianaphthenes, and indoles has been established based on nucleophilic substitution of vinyl halides by an ortho substituent. The dramatic increase of reactivity of vinyl halides upon introduction of lithium has been explained as being due to metal-assisted ionization.

  DOI：

  10.1021/jo00122a046
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1,1-dibromo-2-(2-methoxyphenyl)ethene
  参考文献：
  名称：

  镍和光氧化还原催化的芳基乙烯基卤化物和未活化的叔烷基溴的双重还原交叉偶联†

  摘要：

  通过光氧化还原/镍双重催化已经实现了芳基乙烯基卤化物和未活化的叔烷基溴化物的新型还原性交叉偶联，以产生具有优异的E-选择性的带有全碳四元中心的乙烯基芳烃衍生物。可以通过使用市售的N，N，N '，N'-四甲基乙二胺（TMEDA）作为末端还原剂来避免化学计量的金属还原剂。

  DOI：

  10.1039/c9cc00768g

文献信息

• Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
  作者：Jiandong Liu、Qinghua Ren、Xinghua Zhang、Hegui Gong

  DOI：10.1002/anie.201607959

  日期：2016.12.12

  This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate nickel‐catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional‐group tolerance. The nickel‐catalytic system displays

  这项工作强调了在温和且易于操作的镍催化反应条件下，通过芳基卤化物与乙烯基溴的还原偶联来合成取代的乙烯基芳烃。广泛使用的芳基卤化物，包括杂芳族化合物和乙烯基溴化物，以中等至优异的收率生产了具有高官能团耐受性的产品。镍催化系统在两个C（sp 2）-卤化物偶合体之间显示出良好的化学选择性，从而证明了不同于其他逐步方案的机理途径。
• Nickel‐Catalyzed, Regio‐ and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide
  作者：Jiandong Liu、Hegui Gong、Shaolin Zhu

  DOI：10.1002/anie.202012614

  日期：2021.2.19

  A NiH‐catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using

  已开发出NiH催化的烯烃与烯基溴化物的迁移性加氢烯基化反应，可提供高收率和出色的化学选择性的苄基烯基化产物。该反应的温和条件阻止烯烃产物进行进一步的异构化或随后的烯基化。通过使用手性双恶唑啉配体实现苯乙烯的催化对映选择性加氢烯基化。
• Copper-Catalyzed <i>N</i>-Alkynylations of Sulfoximines with Bromoacetylenes
  作者：Xiao Yun Chen、Long Wang、Marcus Frings、Carsten Bolm

  DOI：10.1021/ol5016898

  日期：2014.7.18

  N-Alkynylated sulfoximines have been obtained by copper-catalyzed cross-coupling reactions starting from NH-sulfoximines and bromoacetylenes in moderate to good yields. The reaction conditions are mild, and the substrate scope is wide.

  Ñ -Alkynylated亚磺酰亚胺已通过从开始铜催化的交叉偶联反应得到Ñ H-亚磺酰亚胺和bromoacetylenes在中度至良好的产率。反应条件温和，底物范围广。
• Visible Light‐Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis
  作者：Liangfeng Yang、Haifeng Li、Yijun Du、Kai Cheng、Chenze Qi

  DOI：10.1002/adsc.201900603

  日期：2019.11.5

  salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely‐functionalized aryl alkynes could be synthesized under mild, neutral and transition metal‐free reaction conditions using visible light irradiation. Alongside synthetic

  开发了一种由光氧化还原催化介导的简便方法，用于直接构建芳基炔烃。现成的芳族重氮盐已被用作芳基自由基源，以偶联炔基羧酸以形成脱羧芳基化。各种各样的底物都适合该方案，具有宽泛的官能团耐受性，并且可以使用可见光在温和，中性和无过渡金属的反应条件下合成功能多样的芳基炔烃。除了与光催化和无过渡金属操作相关的合成可持续性外，该方法的另一个关键点是有机染料催化剂可作为激发态还原剂，从而建立了自由基加成和脱羧消除的淬灭循环。
• 3α-Hydroxy-3β-(phenylethynyl)-5β-pregnan-20-ones:  Synthesis and Pharmacological Activity of Neuroactive Steroids with High Affinity for GABA_A Receptors
  作者：Ravindra B. Upasani、Kevin C. Yang、Manuel Acosta-Burruel、Chris S. Konkoy、James A. McLellan、Richard M. Woodward、Nancy C. Lan、Richard B. Carter、Jon E. Hawkinson

  DOI：10.1021/jm9605344

  日期：1997.1.1

  Neuroactive steroids that allosterically modulate GABAA receptors have potential uses as anticonvulsants, anxiolytics, and sedative-hypnotic agents. Recently, a series of pregnanes substituted with simple alkyl groups at the 3 beta-position were synthesized and found to be active in vitro. The present report describes the synthesis of a series of substituted 3 alpha-hydroxy-3 beta-(phenylethynyl)pregnan-20-ones

  变构调节GABAA受体的神经活性类固醇有潜在用途，可作为抗惊厥药，抗焦虑药和镇静催眠药。最近，合成了一系列在3β位置被简单烷基取代的孕烷，并发现其在体外具有活性。本报告描述了一系列取代的3α-羟基-3β-（苯基乙炔基）pregnan-20-的合成及其通过体外抑制大鼠脑中[35S] TBPS结合力确定的体外结构-活性关系。膜。适当取代苯基会导致配体对GABAA受体上的神经活性类固醇位点具有特别高的亲和力（例如4-乙酰基28，IC50 10 nM）。在表达克隆的人GABAAα1β2γ2L受体（例如化合物28，EC50 6.6 nM）的卵母细胞中，通过电生理学证实了所选类固醇的效力。与它们的体外活性一致，在小鼠腹腔注射后，一些3β-（苯乙炔基）取代的类固醇在戊四氮（PTZ）和最大电击（MES）试验中显示出抗惊厥活性。值得注意的是，3β-[（（4-乙酰基苯基）乙炔基] -19-nor衍生物36表现出有吸引力的抗惊厥特征（PTZ和MES