6-endo-Hydroxy-5-exo-iod-2-exo-methylbicyclo<2.2.1>heptan-2-endo-carbonsaeurelacton | 13432-80-9

• 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: 6-endo-Hydroxy-5-exo-iod-2-exo-methylbicyclo<2.2.1>heptan-2-endo-carbonsaeurelacton
• 英文别名: (+/-)-6c-iodo-3-methyl-(3ar)-hexahydro-3,5-methano-cyclopenta[b]furan-2-one；(+/-)-6c-Jod-3-methyl-(3ar)-hexahydro-3,5-methano-cyclopenta[b]furan-2-on；(1S,2S,3S,6S,7R)-2-iodo-6-methyl-4-oxatricyclo[4.2.1.03,7]nonan-5-one
• CAS: 13432-80-9
• 化学式: C₉H₁₁IO₂
• 分子量: 278.09
• InChiKey: YECMDBLKIWRHSW-OUHXRIGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-endo-Hydroxy-5-exo-iod-2-exo-methylbicyclo<2.2.1>heptan-2-endo-carbonsaeurelacton 在 溶剂黄146 、 锌 作用下， 生成 (2-exo)-methylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid
  参考文献：
  名称：

  Ford,D.N. et al., Australian Journal of Chemistry, 1969, vol. 22, p. 1157 - 1168

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基双环[2.2.1!庚-5-烯-2-羧酸 在 碘 、 碳酸氢钠 、 potassium iodide 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以31%的产率得到6-endo-Hydroxy-5-exo-iod-2-exo-methylbicyclo<2.2.1>heptan-2-endo-carbonsaeurelacton
  参考文献：
  名称：

  使用构象柔性手性超分子催化剂，具有异常内/外选择性的对映选择性Diels-Alder反应

  摘要：

  交换选择性：使用量身定制的催化剂会导致环戊二烯与不同丙烯醛的Diels-Alder反应异常的内/外选择性和高对映选择性（请参阅方案）。这些超分子催化剂在原位制备由手性二醇，芳基硼酸，和三（五氟苯基）硼烷，并且可以区分重新/ SI的亲二烯体的面以及所述内切/外切二烯的方法。

  DOI：

  10.1002/anie.201106497

文献信息

• Rotational selectivity in cyclobutene ring openings. Model studies directed toward a synthesis of verrucarin A
  作者：Barry M. Trost、Patrick G. McDougal

  DOI：10.1021/jo00177a015

  日期：1984.2
• ——
  作者：E.G. Mamedov

  DOI：10.1023/a:1012374828303

  日期：——

  An asymmetrical synthesis of bicyclo[2.2.1]hept-2-enes is described performed by [4+21-cyclo-addition of (-)-menthyl acrylate and (-)-menthyl methacrylate to cyclopentadiene in the presence of BBr3. The effect of different factors on isomer composition, yield, and enantiomeric purity of the compounds obtained was investigated. Kovatch indices were determined and boiling points were estimated with the use of gas-liquid chromatography.
• Structures of the Adducts of Cyclopentadiene and Methacrylic Acid and Some of its Derivatives¹
  作者：John S. Meek、Walter B. Trapp

  DOI：10.1021/ja01571a076

  日期：1957.7
• Enantioselective Synthesis of Cyclothiazide Analogues:  Novel Probes of the Stereospecific Actions of Benzothiadiazines at AMPA-Type Glutamate Receptors
  作者：Yuefei Hu、Kelvin A. Yamada、David K. Chalmers、Durga P. Annavajjula、Douglas F. Covey

  DOI：10.1021/ja9525317

  日期：1996.1.1

  The stereospecific interactions of the eight stereoisomers of dihydromethylcyclothiazide, an analogue of cyclothiazide, with AMPA-type glutamate receptors was investigated using electrophysiological methods that measured the ability of each stereoisomer to inhibit AMPA receptor desensitization. The eight stereoisomers were obtained by HPLC separation of four pairs of enantiomerically pure (>95% ee) diastereomers prepared from (1R-exo)-, (1R-endo)-, (1S-exo)-, and (1S-endo)-2-methylbicyclo[2.2.1]heptane-2-carboxaldehyde intermediates. The desensitization process was blocked most potently by [1S-[1 alpha,2 alpha(R*),4 alpha]]-dihydromethylcyclothiazide, one of the stereoisomers prepared from the (1S-endo)-carboxaldehyde. The smallest effects on the desensitization process were found for the four stereoisomers prepared from the (1R-exo)- and (1R-endo)-carboxaldehydes. Significant differences in the ability to inhibit desensitization were observed between all diastereomer pairs except those prepared from the (1S-exo)-carboxaldehyde.