2-Bromo-2-ethylbutanal | 38562-30-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 2-Bromo-2-ethylbutanal
• 英文别名: 2-bromo-2-ethyl-butyraldehyde；2-Brom-2-ethylbutanal
• CAS: 38562-30-0
• 化学式: C₆H₁₁BrO
• 分子量: 179.057
• InChiKey: VYAFHXKBEDDKRD-UHFFFAOYSA-N

物化性质

• 沸点：
  171.8±13.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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-Bromo-2-ethylbutanal 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 25.0 ℃ 、350.0 kPa 条件下， 反应 19.5h， 生成 1-[(1S,3R)-6-chloro-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]-3,3-diethylpiperazine
  参考文献：
  名称：

  Enhanced D1 Affinity in a Series of Piperazine Ring Substituted 1-Piperazino-3-Arylindans with Potential Atypical Antipsychotic Activity

  摘要：

  A study of the effect of aromatic substitution on D-1 and D-2 affinity in a series of previously reported trans-1-piperazino-3-phenylindans shows similar structure-activity relationships for the two receptor sites. 6-Substituted derivatives have affinity for both receptors, and 6-chloro- or B-fluoro-substituted derivatives show preference for D-1 receptors. D-1 affinity and selectivity are significantly increased in a series of new piperazine ring substituted derivatives. Potent D-1 and D-2 antagonism in vivo are confined to derivatives with relatively small substituents in the 2-position of the piperazine ring (e.g. 2-methyl, 2,2-dimethyl, 2-spirocyclobutyl or 2-spirocyclopentyl). Consequently, the effect of aromatic substitution is examined in a series of 1-(2,2-dimethylpiperazino)-3-arylindans. All these compounds except the 4-, 5-, 7- and 4'-chlorosubstituted derivatives have potent D-1 affinity (IC50's below 10 nM) and the majority of the compounds antagonize SK&F 38393-induced circling in 6-OHDA-lesioned rats with ED(50) values about 1 mu mol/kg. In vitro all compounds show preference for D-1 receptors, but in vivo they are equally effective as D-1 and D-2 antagonists. The compounds have high affinity for 5-HT2 receptors and selected compounds show high affinity for alpha(1) adrenoceptors. Furthermore, a subgroup consisting of (-)-38, (-)-39, (-)-41, and (-)-54 does not induce catalepsy in rats. These compounds have the potential of being ''atypical'' antipsychotics and have consequently been selected for further studies. The non-receptor-blocking enantiomers are shown to be inhibitors of DA and NE uptake in accordance with previous observations in compounds unsubstituted in the piperazine ring. Two compounds, (+)-38 and (+)-40, block DA uptake with IC50 values below 10 nM. Finally, the observed structure-activity relationships are discussed in relation to previously published pharmacophore models for D-2 and 5-HT2 receptors. It is concluded that the piperazine substituents might induce a different binding mode at the dopamine receptor sites, perhaps only at the D-1 receptor site.

  DOI：

  10.1021/jm00022a004
• 作为产物：
  描述：

  2-乙基丁醛 在 溴 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 以60%的产率得到2-Bromo-2-ethylbutanal
  参考文献：
  名称：

  立体控制的 1,3-磷酸酯氧基和 1,3-卤素向高官能化 1,3-二烯的迁移中继

  摘要：

  α-卤素取代的炔丙磷酸酯的双迁移级联反应已被开发出来，以生产高度功能化的 1,3-二烯。这种转变的特点是 1,3-磷酰氧基迁移，随后是溴和氯的 1,3-位移以及史无前例的碘 1,3-迁移。该反应是立体发散的：在铜催化剂存在下形成(Z)-1,3-二烯，而金催化的反应表现出反向立体选择性，产生相应的E产物。

  DOI：

  10.1021/ja301243t

文献信息

• General Route for Preparing β-Nitrocarbonyl Compounds Using Copper Thermal Redox Catalysis
  作者：Amber A. S. Gietter、Peter G. Gildner、Andrew P. Cinderella、Donald A. Watson

  DOI：10.1021/ol5014153

  日期：2014.6.6

  Using a simple copper catalyst, the alkylation of nitroalkanes with α-bromocarbonyls is now possible. This method provides a general, functional group tolerant route to β-nitrocarbonyl compounds, including nitro amides, esters, ketones, and aldehydes. The highly sterically dense, functional group rich products from these reactions can be readily elaborated into a range of complex nitrogen-containing

  使用简单的铜催化剂，硝基烷烃与 α-溴代羰基化合物的烷基化现在成为可能。该方法为β-硝基羰基化合物（包括硝基酰胺、酯、酮和醛）提供了一种通用的、官能团耐受的途径。来自这些反应的高空间密度、富含官能团的产物可以很容易地加工成一系列复杂的含氮分子，包括高度取代的 β-氨基酸。
• “Home-pictet-spengler” cyclization of tryptamines: an easy access to the hexahydroazepino[4,5-b]indole ring system.
  作者：Jean-Yves Laronze、Christine Gauvin-Hussenet、Jean Lévy

  DOI：10.1016/s0040-4039(00)74842-8

  日期：1991.1

  The title compounds were prepared in one step from tryptamines 3 and α-bromoaldehydes 4.

  由色胺3和α-溴醛4一步制备标题化合物。
• Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides
  作者：Xuan Wang、Guobin Ma、Yu Peng、Chloe E. Pitsch、Brenda J. Moll、Thu D. Ly、Xiaotai Wang、Hegui Gong

  DOI：10.1021/jacs.8b09473

  日期：2018.10.31

  This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation

  这项工作说明了富电子芳基卤化物与叔烷基卤化物在 Ni 催化的交叉亲电偶联条件下的还原偶联，为构建所有碳四元立体中心提供了有效的方案。温和且易于操作的反应可耐受广泛的官能团。该方法的实用性通过环色胺衍生物的制备得到证明，其中成功掺入 7-吲哚基部分特别令人感兴趣，因为许多天然产物由这些关键支架组成。已经进行了 DFT 计算以研究提议的自由基链和双氧化加成途径，这为在溶液中发生的反应部分提供了有用的机理见解。
• Reductive cyclization caused by cobaloxime. I. A new method for the synthesis of .beta.-methylene-.gamma.-butyrolactones
  作者：Masami Okabe、Masaru Tada

  DOI：10.1021/jo00148a027

  日期：1982.12
• Dehalogenation of .alpha.-halo aldehydes via .alpha.-halo aldimines and 2-aza-1,3-dienes
  作者：Norbert De Kimpe、Milan Nagy、Marc Boeykens、Danny Van der Schueren

  DOI：10.1021/jo00047a034

  日期：1992.10