cis-1,3-dibromo-2-methyl-1-propene | 28357-77-9

• 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: cis-1,3-dibromo-2-methyl-1-propene
• 英文别名: 1,3-(Z)-dibromo-2-methyl-propene；Z-1,3-dibromo-2-methyl-1-propene；(Z)-2-methyl-1,3-dibromopropene；(Z)-1,3-dibromo-2-methylprop-1-ene
• CAS: 28357-77-9
• 化学式: C₄H₆Br₂
• 分子量: 213.9
• InChiKey: ZGUSGHWDLWVHBI-RQOWECAXSA-N

物化性质

• 沸点：
  176.0±23.0 °C(Predicted)
• 密度：
  1.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  cis-1,3-dibromo-2-methyl-1-propene 、 5,6-dimethoxy-2-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid methyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以80%的产率得到3-((Z)-3-Bromo-2-methyl-allyl)-5,6-dimethoxy-3,4-dihydro-1H-naphthalen-2-one
  参考文献：
  名称：

  Synthesis of (−)-Morphine

  摘要：

  The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1.

  DOI：

  10.1021/ja027882h
• 作为产物：
  描述：

  1-甲基环丙烯 生成 cis-1,3-dibromo-2-methyl-1-propene
  参考文献：
  名称：

  NESMEYANOVA, O. A.;KUDRYAVTSEVA, G. A., IZV. AN CCCP. CEP. XIM., 1982, N 11, 2629-2630

  摘要：

  DOI：

文献信息

• Kartashov, V. R.; Skorobogatova, E. V.; Afanas'ev, P. S., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 9.1, p. 1639 - 1648
  作者：Kartashov, V. R.、Skorobogatova, E. V.、Afanas'ev, P. S.、Chertkov, V. A.、Sergeev, N. M.、et al.

  DOI：——

  日期：——
• Kartashov, V. R.; Afanas'ev, P. S.; Skorobogatova, E. V., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 400 - 401
  作者：Kartashov, V. R.、Afanas'ev, P. S.、Skorobogatova, E. V.、Grishin, Yu. K.、Zefirov, N. S.

  DOI：——

  日期：——
• Enantioselective Total Syntheses of Omuralide, 7-<i>epi</i>-Omuralide, and (+)-Lactacystin
  作者：Christopher J. Hayes、Alexandra E. Sherlock、Martin P. Green、Claire Wilson、Alexander J. Blake、Matthew D. Selby、Jeremy C. Prodger

  DOI：10.1021/jo7027695

  日期：2008.3.1

  An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.
• Synthesis of (−)-Morphine
  作者：Douglass F. Taber、Timothy D. Neubert、Arnold L. Rheingold

  DOI：10.1021/ja027882h

  日期：2002.10.1

  The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1.
• NESMEYANOVA, O. A.;KUDRYAVTSEVA, G. A., IZV. AN CCCP. CEP. XIM., 1982, N 11, 2629-2630
  作者：NESMEYANOVA, O. A.、KUDRYAVTSEVA, G. A.

  DOI：——

  日期：——