2,2-cis-Vinyl-trans-methylcyclopropylbromid | 60288-35-9

• 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: 2,2-cis-Vinyl-trans-methylcyclopropylbromid
• 英文别名: (1S,2S)-2-bromo-1-ethenyl-1-methylcyclopropane
• CAS: 60288-35-9；60288-36-0；71153-25-8；146563-19-1
• 化学式: C₆H₉Br
• 分子量: 161.041
• InChiKey: UUPJLMPNKOANAN-NTSWFWBYSA-N

物化性质

• 沸点：
  46-48 °C(Press: 28 Torr)
• 密度：
  1.506±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,2-cis-Vinyl-trans-methylcyclopropylbromid 、 4-[Tert-butyl(dimethyl)silyl]oxy-4-(2-iodophenyl)butanal 生成
  参考文献：
  名称：

  Total Synthesis of (±)-Scopadulcic Acid B

  摘要：

  The first total synthesis of a scopadulan diterpene is described. The key step is a double Heck cyclization of dienyl aryl iodide 8 to form tetracyclic enones 24 and 25 in 80-85% combined yield.

  DOI：

  10.1021/ja972427k
• 作为产物：
  描述：

  1,1-二溴-2-乙烯基-2-甲基环丙烷 在 三正丁基氢锡 作用下， 生成 2,2-cis-Vinyl-trans-methylcyclopropylbromid
  参考文献：
  名称：

  Sydnes,L.K., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 47 - 55

  摘要：

  DOI：

文献信息

• Yakushkina, N. I.; Zakharova, G. A.; Surmina, L. S., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1553 - 1557
  作者：Yakushkina, N. I.、Zakharova, G. A.、Surmina, L. S.、Bolesov, I. G.

  DOI：——

  日期：——
• Electrochemical reduction of 1,1-dihalo-2,2-disubstituted cyclopropanes
  作者：Yu. M. Kargin、E. I. Gritsenko、V. V. Yanilkin、V. V. Plemenkov、L. K. Dubovik、N. I. Maksimyuk、B. M. Garifullin、Sh. K. Letypov、A. V. Il'yasov

  DOI：10.1007/bf00863575

  日期：1992.9

  The electrochemical reduction of 1,1-dihalo-2-R-2-methylcyclopropanes was studied by polarography and preparative electrolysis. A mixture of stereoisomeric monoboro- and monochlorocyclopropanes was obtained with preparative yield of 60-70% in preparative electroreduction in methanol against a background of 0.1 M LiClO4. In the case of bromine derivatives of cyclopropanes (except when R = CN) an effect was found on the part of the current density on the ratio of cis and trans isomers, which was interpreted as a change, in dependence on current density, of the contributions of the reactions of reduction of the starting compounds (SN2 mechanism) and ionic pairs (S(N)1 mechanism). The effect of the solvent (CHCl3, DMF, DMSO, MeOH) and background salt (LiClO4, Et4NBr) on the ratio of stereoisomers is in agreement with this interpretation.
• Sydnes,L.K., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 47 - 55
  作者：Sydnes,L.K.

  DOI：——

  日期：——
• Total Synthesis of (±)-Scopadulcic Acid B
  作者：Larry E. Overman、Daniel J. Ricca、Vinh D. Tran

  DOI：10.1021/ja972427k

  日期：1997.12.17

  The first total synthesis of a scopadulan diterpene is described. The key step is a double Heck cyclization of dienyl aryl iodide 8 to form tetracyclic enones 24 and 25 in 80-85% combined yield.