(3aS,5aS,6aS,6bS)-2,2-dimethyloxirano[2',3':3,4]benzo[d][1,3]dioxol-4-yl bromide | 192448-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,5aS,6aS,6bS)-2,2-dimethyloxirano[2',3':3,4]benzo[d][1,3]dioxol-4-yl bromide
• 英文别名: (3aS,5aS,6aS,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole
• CAS: 192448-69-4
• 化学式: C₉H₁₁BrO₃
• 分子量: 247.089
• InChiKey: IJFOOAYHPAECGI-FKSUSPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,5aS,6aS,6bS)-2,2-dimethyloxirano[2',3':3,4]benzo[d][1,3]dioxol-4-yl bromide 在 氢氧化钾 、 四氧化锇 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 90.0h， 生成 (3aS,4S,5R,6S,7S,7aR)-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-4,5,6,7-tetrol
  参考文献：
  名称：

  A short, stereoselective synthesis of neo-inositol

  摘要：

  A practical synthesis of neo-inositol is described in which the target is prepared on a multigram scale in six operations from bromobenzene. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00289-x
• 作为产物：
  描述：

  (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 在 sodium hydroxide 、 N-碘代丁二酰亚胺 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 (3aS,5aS,6aS,6bS)-2,2-dimethyloxirano[2',3':3,4]benzo[d][1,3]dioxol-4-yl bromide
  参考文献：
  名称：

  Selectivity in the halohydroxylation of cyclohexadienediols

  摘要：

  The halohydroxylation of a number of cyclohexadienediol derivatives has been investigated. The selectivity of the reaction as a function of the type of substituent on the diene, protecting group of the diol functionality, halonium donor, medium polarity, and temperature is described. Best selectivity is obtained for iodohydrin formation. The course of the reaction for these dienic systems is heavily dependent on steric factors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.109

文献信息

• Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds
  作者：Germán Fonseca、Gustavo A. Seoane

  DOI：10.1016/j.tetasy.2005.02.012

  日期：2005.4

  A series of chiral alpha-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclo-hexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of alpha-chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of deoxyfluoroinositols: 5-deoxy-5-fluoro-myo-inositol and 3-deoxy-3-fluoro-L-chiro-inositol
  作者：Ba V. Nguyen、Chentao York、Tomas Hudlicky

  DOI：10.1016/s0040-4020(97)90392-6

  日期：1997.6
• Chemoenzymatic Synthesis and Biological Evaluation of (−)‐Conduramine C‐4
  作者：Ana Bellomo、Cecilia Giacomini、Beatriz Brena、Gustavo Seoane、David Gonzalez

  DOI：10.1080/00397910701555725

  日期：2007.10.1

  Previously unreported (-)-conduramine C-4 was synthesized in six steps from a bacterial bromobenzene metabolite in 23% overall yield. The chemoenzymatic route involved toluene dioxygenase dihydroxylation, beta-epoxidation, epoxide ring-opening, Staudinger reduction, radical debromination, and Amberlite- catalyzed hydrolysis. (-)-Conduramine C-4 and other related compounds synthesised were assayed for galactosidase-activity inhibition against (beta-D-galactoside galactohidrolase isolated from Aspergillus oryzae.
• Diasterodivergent synthesis of optically pure vinyl episulfides and β-hydroxy thiocyanates from a bacterial metabolite
  作者：Ana Bellomo、David Gonzalez

  DOI：10.1016/j.tetlet.2007.02.113

  日期：2007.4

  Diasterodivergent episulfides were chemoenzymatically derived from bromobenzene by sequential toluene dioxygenase dihydroxylation, followed by chemical epoxidation and thiolysis. The epoxide ring-opening by thiocyanate ion under literature conditions rendered the corresponding hydroxy thiocyanates and not the thiiranes as usually observed. Ring closing under carefully optimized conditions allowed the preparation of optically pure thiiranes that are key precursors for the preparation of thioconduritols and pseudodisaccharides. (c) 2007 Elsevier Ltd. All rights reserved.
• Selectivity in the halohydroxylation of cyclohexadienediols
  作者：Ignacio Carrera、Margarita C. Brovetto、Gustavo Seoane

  DOI：10.1016/j.tet.2007.02.109

  日期：2007.5

  The halohydroxylation of a number of cyclohexadienediol derivatives has been investigated. The selectivity of the reaction as a function of the type of substituent on the diene, protecting group of the diol functionality, halonium donor, medium polarity, and temperature is described. Best selectivity is obtained for iodohydrin formation. The course of the reaction for these dienic systems is heavily dependent on steric factors. (C) 2007 Elsevier Ltd. All rights reserved.