(Z)-2-Bromo-2-heptene | 60254-60-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-2-Bromo-2-heptene
• 英文别名: z-2-Bromo-2-heptene；(Z)-2-bromohept-2-ene
• CAS: 60254-60-6
• 化学式: C₇H₁₃Br
• 分子量: 177.084
• InChiKey: RKVDDVFLMCHSFM-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-2-Bromo-2-heptene 、 碘乙烷 生成 (Z)-3-methyl-oct-3-ene
  参考文献：
  名称：

  Stereoselective trisubstituted olefin synthesis via vinylsilanes

  摘要：

  DOI：

  10.1021/jo00393a035
• 作为产物：
  描述：

  (E)-(1-methyl-1-hexenyl)trimethylsilane 生成 (Z)-2-Bromo-2-heptene
  参考文献：
  名称：

  Stereoselective trisubstituted olefin synthesis via vinylsilanes

  摘要：

  DOI：

  10.1021/jo00393a035

文献信息

• Alkenyl Bromides by Brominative Deoxygenation of Ketones in One or Two Steps
  作者：Ulrich Von Roman、Jakob Ruhdorfer、Rudolf Knorr

  DOI：10.1055/s-1993-25986

  日期：——

  The conversion of ketones into alkenyl bromides is accomplished in one or two steps by 2,2,2-tribromo-2,2-dihydro-1,3,2-benzodioxaphosphole or by the dibromomethyl methyl ether prepared therefrom. Investigations of the scope and limitations provide some hints for the preparative planning and improvement.

  通过使用2,2,2-三溴-2,2-二氢-1,3,2-苯并二氧磷杂环己烯或由此制备的二溴甲基甲醚，可以将酮转化为烯基溴，这一过程在一到两步内完成。对范畴和限制条件的研究为制备规划和改进提供了一些线索。
• A simple conversion of [E]- into the isomeric [Z]-2-(1-substituted-1-alkenyl)-1,3,2-dioxaborinanes, providing a convenient stereospecific synthesis of both [E]- and [Z]-1,2-disubstituted vinyl bromides
  作者：Herbert C. Brown、Narayan G. Bhat

  DOI：10.1016/0040-4039(88)80005-4

  日期：——

  A highly stereo- and regioselective conversion of [E]- into [Z]-2-(1-substituted-l-alkenyl)-1,3,2-dioxaborinane has been achieved for the first time. Treatment of these boronic acid esters with bromine, followed by base, produces either [Z]- or [E]-disubstituted vinyl bromides in good yields (76–81%) and excellent stereochemical purities (> 99%). Replacement of boron moiety with bromine proceeds with

  首次实现了[ E ]-到[ Z ] -2-（1-取代-1-烯基）-1,3,2-二氧杂硼烷的高度立体和区域选择性转化。用溴，然后用碱处理这些硼酸酯，可制得[ Z ]-或[ E ]-二取代的乙烯基溴化物，收率好（76-81％），立体化学纯度也好（> 99％）。用溴取代硼部分进行完全转化。
• Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes
  作者：Paul J. Kropp、Scott D. Crawford

  DOI：10.1021/jo00090a031

  日期：1994.6

  The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a. On extended treatment (E)-4a underwent subsequent isomerization to the thermodynamically more stable Z isomer. Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions. In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution. In contrast with solution-phase hydriodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer. E reversible arrow Z equilibration of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides 13. Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation. Surface-mediated addition of Hbr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c. Treatment of the terminal alkynes 17 and 22 with (COBr)(2) over alumina gave the dibromides 20 and 24/25,respectively, whereas use of acetyl bromide as the Hbr precursor afforded the alkenyl bromides 18b and 23.
• BROWN, HERBERT C.;BHAT, NARAYAN G., TETRAHEDRON LETT., 29,(1988) N 1, 21-24
  作者：BROWN, HERBERT C.、BHAT, NARAYAN G.

  DOI：——

  日期：——