(1R,2S,3R,4S,5S,6R)-5,6-dibromobicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride | 63179-93-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,3R,4S,5S,6R)-5,6-dibromobicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride
• 英文别名: cis-5,6-dibromobicyclo(2.2.1.)heptane-endo-2,3-dicarboxylic anhydride；meso-5-exo,6-exo-dibromobicyclo[2.2.1]heptane-2-endo,3-endo-dicarboxylic anhydride；5exo,6exo-dibromo-norbornane-2endo,3endo-dicarboxylic acid-anhydride；5exo,6exo-Dibrom-norbornan-2endo,3endo-dicarbonsaeure-anhydrid；(1R,2S,6R,7S,8S,9R)-8,9-dibromo-4-oxatricyclo[5.2.1.02,6]decane-3,5-dione
• CAS: 63179-93-1
• 化学式: C₉H₈Br₂O₃
• 分子量: 323.969
• InChiKey: HHFFMUZIOYHTFC-CTJUJGJMSA-N

物化性质

• 熔点：
  209-210 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  430.1±45.0 °C(Predicted)
• 密度：
  2.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S,5S,6R)-5,6-dibromobicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 在 水 作用下， 以 丙酮 为溶剂， 以76%的产率得到(1R,2S,3R,4S,5S,6R)-5,6-dibromobicyclo[2.2.1]heptane-2,3-dicarboxylic acid
  参考文献：
  名称：

  Phase Transitions In Bicyclic Compounds

  摘要：

  DOI：

  10.1080/00268948408070401
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 二氯甲烷 、 溴 作用下， 生成 (1R,2S,3R,4S,5S,6R)-5,6-dibromobicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  cis-Addition in the Bromination of Bicyclic Olefins. The Structure and Stereochemistry of the Dibromides of exo-cis-3,6-Endoxo-Δ⁴-tetrahydrophthalic Anhydride and endo-cis-3,6-Endomethylene-Δ⁴-tetrahydrophthalic Anhydride¹

  摘要：

  DOI：

  10.1021/ja01645a002

文献信息

• Synthetic studies in a tetrafluorotricyclo[5.2.1.02,6]decane series
  作者：Ireneusz Nowak

  DOI：10.1016/s0022-1139(00)00219-0

  日期：2000.7

  Tricyclic model alkene (3,3,5,5-tetrafluoro-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene (1)) was obtained in a short two-step procedure involving the use of sulfur tetrafluoride as a fluorinating agent. Addition of electrophiles to unhindered exo face of the CC bond occurs easily, and thus, precludes the possibility of deactivating electronic interaction between fluorine atoms and the π electrons of the double

  三环模型烯烃（3,3,5,5-四氟-4-氧杂-三环[5.2.1.0 2,6 ] dec-8-烯（1））是通过短时的两步操作（包括使用硫）获得的四氟化物作为氟化剂。亲电试剂容易加到CC键不受阻碍的外表面，因此排除了使氟原子与双键π电子之间的电子相互作用失活的可能性。提供了将多环烯烃中的空间位阻与氟原子的存在联系起来的简短讨论。
• Isomerism in the Diels-Alder Reaction. IV. Directive Influences in Addition Reactions of the Double Bond in Bicyclic Adducts^1,2
  作者：Harold Kwart、Lloyd Kaplan

  DOI：10.1021/ja01645a005

  日期：1954.8
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1933, vol. 504, p. 216,232, 252
  作者：Alder、Stein

  DOI：——

  日期：——
• The role of neat substrates in phase-vanishing and tandem phase-vanishing reactions
  作者：Nicole Windmon、Veljko Dragojlovic

  DOI：10.1016/j.tetlet.2008.09.007

  日期：2008.11

  Phase-vanishing reactions are triphasic reactions, which involve a reagent, a liquid perfluoroalkane as a phase screen and a Substrate. Aromatization, isomerization and halogenation of neat Substrates under phase-vanishing conditions gave the expected products in good to excellent yields. In tandem single-phase-phase-vanishing reaction, two reactants, placed in the top phase, afforded the intermediate, which in a Subsequent phase-vanishing reaction reacted with the reagent from the bottom phase to give the final product. The reaction worked well under solvent-free conditions on liquid Substrates and intermediates. With solids, results were better if an additional solvent was employed. (C) 2008 Elsevier, Ltd. All rights reserved.
• Endo-Exo-Rearrangement in the Addition of Acids to Dicyclopentadiene
  作者：Paul D. Bartlett、Abraham Schneider

  DOI：10.1021/ja01205a002

  日期：1946.1