(1R,2R)-3,3-dimethyl-2-norbornanol | 79896-06-3

• 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,2R)-3,3-dimethyl-2-norbornanol
• 英文别名: camphenilol；(-)(1S)-2.2-Dimethyl-norbornanol-(3endo)；(-)-endo-Camphenilol；(1R,2R,4S)-3,3-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 79896-06-3
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: HXUXMDQJDDDOIJ-GJMOJQLCSA-N

物化性质

• 沸点：
  199.1±8.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

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：

  (1R,2R)-3,3-dimethyl-2-norbornanol 生成 3,3-二甲基二环[2.2.1]庚烷-2-酮
  参考文献：
  名称：

  MUNEYUKI, RYONOSUKE;YOSHIMURA, YOHKO;TORI, KAZUO;TERUI, YOSHIHIRO;SHOOLER+, J. ORG. CHEM., 53,(1988) N 2, 358-366

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-camphenilone 在 (+)-β-chlorodiisopinocampheylborane 、 二乙醇胺 作用下， 生成 (1R,2R)-3,3-dimethyl-2-norbornanol
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 43. Selective Reductions. 58. Reagent-Controlled Diastereoselective Reduction of (+)- and (−)-α-Chiral Ketones with (+)- and (−)-B-Chlorodiisopinocampheylborane

  摘要：

  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.

  DOI：

  10.1021/jo951207r

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; Tappe, Chemische Berichte, 1936, vol. 69, p. 2769,2771
  作者：Hueckel、Tappe

  DOI：——

  日期：——
• Robustadials. 3. Total synthesis of camphane analogs
  作者：Samuel M. Mazza、Kasturi Lal、Robert G. Salomon

  DOI：10.1021/jo00251a006

  日期：1988.8
• KIRMSE, W.;BRANDT, S., CHEM. BER., 1984, 117, N 7, 2510-2523
  作者：KIRMSE, W.、BRANDT, S.

  DOI：——

  日期：——
• KOWALSKI C.; CREARY X.; ROLLIN A. J.; BURKE M. C., J. ORG. CHEM., 1978, 43, NO 13, 2601-2608
  作者：KOWALSKI C.、 CREARY X.、 ROLLIN A. J.、 BURKE M. C.

  DOI：——

  日期：——