3,3-dimethylbicyclo<2.2.1>heptan-endo-2-ol | 640-54-0

• 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: 3,3-dimethylbicyclo<2.2.1>heptan-endo-2-ol
• 英文别名: (+/-)-endo-Camphenilol；(+/-)-2.2-Dimethyl-norbornanol-(3endo)；2-endo-Hydroxy-3,3-dimethyl-norbornan；3,3-Dimethyl-2-endo-norbornanol；(+/-)-endo-Camphenilol；endo-Camphenilol；(1S,2S,4R)-3,3-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 640-54-0
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: HXUXMDQJDDDOIJ-RNJXMRFFSA-N

物化性质

• 沸点：
  199.1±8.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)
• 熔点：
  75-77 °C (sublm)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-dimethylbicyclo<2.2.1>heptan-endo-2-ol 、 6-氯嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到6-chloro-9-[(1R*,2S*,4S*)-3,3-dimethylbicyclo[2.2.1]hept-2-yl]-9H-purine
  参考文献：
  名称：

  新型柯萨奇病毒B3抑制剂的设计，合成和生物学评估

  摘要：

  报道了新型的柯萨奇病毒B3（CVB3）抑制剂的合成和SAR研究。这些化合物可视为在9位被各种取代的双环支架（双环[2.2.1]庚烷/烯-降冰片烷或降冰片烯）取代的6-氯嘌呤。描述了31种目标化合物的合成和生物学评估。几种类似物在低微摩尔范围（0.66–2μM）中抑制CVB3。观察到最小或没有细胞毒性。

  DOI：

  10.1016/j.bmc.2010.04.081
• 作为产物：
  描述：

  dl-camphene 在 甲醇 、 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 3,3-dimethylbicyclo<2.2.1>heptan-endo-2-ol
  参考文献：
  名称：

  Hueckel; Gelchsheimer, Suomen Kemistilehti B, 1958, vol. 31, p. 13,15

  摘要：

  DOI：

文献信息

• Chiral Synthesis via Organoboranes. 42. Selective Reductions. 57. Efficient Kinetic Resolution of Representative α-Tertiary Ketones with <i>B</i>-Chlorodiisopinocampheylborane
  作者：P. Veeraraghavan Ramachandran、Guang-Ming Chen、Herbert C. Brown

  DOI：10.1021/jo951206z

  日期：1996.1.1

  Kinetic resolution of racemic alpha-tertiary ketones with 0.5-0.6 molar equiv of B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric and enantiomeric excess, with the unreacted ketone recovered in very high ee. For example, ethyl 1-methyl-8-oxocyclopentane- and -cyclohexanecarboxylates are partially reduced to recover the ketone in 91 greater than or equal to 99% ee and the product alcohols in up to 94% de, with >90% ee for the major diastereomer. Bicyclic ketones, such as 1-methyl- and 1-ethylnorcamphor, camphor, and camphenilone, are readily resolved to provide the ketone in 92 to greater than or equal to 99% ee, with the product alcohol recovered in high de and ee. Dihydrospiro[bicyclo[3.2.1]octane-2,2'(3'H)-furan]-3-one is resolved to provide the ketone in greater than or equal to 99% ee and the product alcohol in greater than or equal to 99% de. In all the cases studied, the R-isomer of the ketone is recovered when (d)Ipc(2)BCl is used for kinetic resolution, while (l)Ipc(2)BCl provides the S-ketone. Optimum conditions for obtaining the product alcohol, or the ketone, or both, in very high yields and ee have been established.
• Hueckel, Justus Liebigs Annalen der Chemie, 1941, vol. 549, p. 186,206
  作者：Hueckel

  DOI：——

  日期：——
• Hirsjaervi, Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1957, # 81, p. 13
  作者：Hirsjaervi

  DOI：——

  日期：——
• Chiral Synthesis via Organoboranes. 43. Selective Reductions. 58. Reagent-Controlled Diastereoselective Reduction of (+)- and <b>(</b><b>−</b><b>)-</b>α-Chiral Ketones with (+)- and (−)-<i>B</i>-Chlorodiisopinocampheylborane
  作者：P. Veeraraghavan Ramachandran、Guang-Ming Chen、Herbert C. Brown

  DOI：10.1021/jo951207r

  日期：1996.1.1

  Asymmetric reduction of (+)- and (-)-alpha-chiral ketones with (+)- and (-)-B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric excess, with the matched pairs providing >100:1 selectivity and the mismatched pairs showing 4:1-15:1 selectivity. The high selectivity achieved even in the mismatched pairs reveals the power of the reagent to control the stereochemical outcome. The rates of the reaction of the matched pairs are faster than those of the mismatched pairs, In all the cases studied thus far, the (-)-reagent ((d)Ipc(2)BCl) and (S)ketone or the (+)-reagent ((l)Ipc(2)BCl) and (R)-ketone constitute matched pairs and the (-)-reagent and (R)-ketone or the (+)-reagent and (S)-ketone constitute mismatched pairs, A possible mechanism for the reductions is discussed.
• Alicyclic reaction mechanisms. 7. The predominance and quantification of steric effects in the solvolysis of secondary aliphatic esters
  作者：Hans Joerg Schneider、Norman Becker、Guenther Schmidt、Fred Thomas

  DOI：10.1021/jo00369a010

  日期：1986.9