(-)-camphenilone | 50896-19-0

• 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: (-)-camphenilone
• 英文别名: 3,3-Dimethylbicyclo<2.2.1>heptan-2-one；(1R)-camphenilone；(1S)-3,3-dimethyl-2-norbornanone；(1R)-3,3-dimethyl-norbornan-2-one；(R)-3,3-dimethyl-bicyclo[2.2.1]heptan-2-one；(1R)-3,3-Dimethyl-norbornan-2-on；(-)-Camphenilon；(1R,4S)-3,3-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 50896-19-0
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: ZYPYEBYNXWUCEA-RQJHMYQMSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  196.3±8.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (-)-莰烯 在 乙酸乙酯 作用下， 生成 (-)-camphenilone
  参考文献：
  名称：

  Bartlett et al., Justus Liebigs Annalen der Chemie, 1959, vol. 623, p. 217,247

  摘要：

  DOI：

文献信息

• [EN] NICOTINIC RECEPTOR NON-COMPETITIVE ANTAGONISTS<br/>[FR] ANTAGONISTES NON COMPÉTITIFS DU RÉCEPTEUR NICOTINIQUE
  申请人：TARGACEPT INC

  公开号：WO2014004417A1

  公开（公告）日：2014-01-03

  The present invention relates to compounds that modulate nicotinic receptors as non-competitive antagonists, methods for their synthesis, methods for their use, and their pharmaceutical compositions.

  本发明涉及调节尼古丁受体的化合物，作为非竞争性拮抗剂，其合成方法，使用方法以及它们的药物组合物。
• Mechanisms of Racemization of Camphene-8-C¹⁴¹
  作者：John D. Roberts、Joel A. Yancey

  DOI：10.1021/ja01109a037

  日期：1953.7

  camphene racemizes by at least two different mechanisms in the presence of hydrated titanium dioxide, pyruvic acid or aniline hydrochloride. One of these mechanisms does not cause isotope-position rearrangement of camphene-8-C^(14) and probably involves successive hydride and Wagner rearrangements. This mechanism predominates with hydrated titanium dioxide and aniline hydrochloride. Racemization of camphene-8-C^(14)

  C^(14)-示踪剂研究表明，在水合二氧化钛、丙酮酸或苯胺盐酸盐的存在下，光学活性莰烯通过至少两种不同的机制外消旋化。其中一种机制不会引起莰烯-8-C^(14) 的同位素位置重排，并且可能涉及连续的氢化物和瓦格纳重排。这种机制在水合二氧化钛和苯胺盐酸盐中占主导地位。莰烯-8-C^(14) 与丙酮酸的外消旋化伴随着广泛的同位素位置重排，并且通过假设对映体“莰菔鎓”（莰烯-氢）阳离子通过甲基转移（Nametkin 重排）的相互转化而精心制定。
• [EN] COMPOSITIONS AND METHODS RELATED TO DI-SUBSTITUTED BICYCLO[2.2.1] HEPTANAMINE-CONTAINING COMPOUNDS<br/>[FR] COMPOSITIONS ET PROCÉDÉS ASSOCIÉS À DES COMPOSÉS CONTENANT DE LA BICYCLO[2.2.1] HEPTANAMINE DI-SUBSTITUÉS
  申请人：BROAD INST INC

  公开号：WO2022140677A1

  公开（公告）日：2022-06-30

  The present disclosure relates to compositions and methods related to bicyclo[2.2.1] heptanamine-containing compounds and salts.

  本申请涉及含有bicyclo[2.2.1]heptanamine化合物及其盐的组合物和方法。
• 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.
• Vilkas,M.; Abraham,N.A., Bulletin de la Societe Chimique de France, 1960, p. 1196 - 1201
  作者：Vilkas,M.、Abraham,N.A.

  DOI：——

  日期：——