(1R)-(+)-camphor | 13854-85-8

• 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)-(+)-camphor
• 英文别名: (1S)-(-)-Camphor；(+)-camphor；(+)-epicamphor；(+)-Epicampher；(1R)-4,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one；Epicampher；(1R,4R)-4,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 13854-85-8
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: HFQTYOGWDNGZMS-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (1R)-(+)-camphor 在 sodium ethanolate 作用下， 生成 莰烷
  参考文献：
  名称：

  Alder; Windemuth, Justus Liebigs Annalen der Chemie, 1940, vol. 543, p. 56,60, 67

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S)-3,3-ethylenedioxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one 在 sodium amalgam 、 乙醇 作用下， 生成 (1R)-(+)-camphor
  参考文献：
  名称：

  樟脑的转变

  摘要：

  硼烷-2，3-二酮的单和二亚乙基缩酮已被用于该分子的选择性反应，包括新的环氧树胶途径。樟脑与钠和甲基碘的烷基化得到C-和O-烷基化。文献中有关同型樟脑和同型表足的合成存在的分歧已得到纠正。9-溴硼烷-2-酮与锌和乙酸-aid-d 1的反应既得到了9-氘代化合物，又得到了片段化反应的产物。

  DOI：

  10.1016/s0040-4020(01)82472-8

文献信息

• Transition Metal Complexes in Organic Synthesis, Part 49. Development of Novel Chiral Catalysts for the Asymmetric Catalytic Complexation of Prochiral Cyclohexa-1,3-dienes by the Tricarbonyliron Fragment - Mechanism of the Asymmetric Catalysis and Involvement of a Dinuclear Iron Cluster
  作者：Hans-Joachim Knölker、Helmut Goesmann、Holger Hermann、Daniela Herzberg、Guy Rohde

  DOI：10.1055/s-1999-2626

  日期：1999.4

  Planar-chiral tricarbonyliron-diene complexes are obtained quantitatively in up to 73% ee by asymmetric catalytic complexation of prochiral cyclohexa-1,3-dienes. A series o novel chiral 1-azabuta-1,3-diene catalysts is investigated. The mechanism is shown to involve at least in some cases dinuclear iron cluster compounds which lead to a lower asymmetric induction.

  平面手性三羰基铁-二烯配合物通过非手性环己-1,3-二烯的不对称催化配合反应，以高达73%的ee值定量获得。研究了一系列新颖的手性1-氮杂巴-1,3-二烯催化剂。机制表明，至少在某些情况下涉及二核铁簇化合物，导致了较低的不对称诱导效果。
• Further studies on the activation of the CH bond in saturated hydrocarbons
  作者：Derek H.R. Barton、Robyn S. Hay-Motherwell、William B. Motherwell

  DOI：10.1016/s0040-4039(00)81821-3

  日期：1983.1

  Various saturated aliphatic and alicyclic hydrocarbons have been regioselectively oxidised with surprising efficiency by a system containing iron powder and a carboxylic acid in aqueous pyridine under an atmosphere of oxygen. A trace of hydrogen sulphide initiates the reaction.

  各种饱和的脂族和脂环族烃已通过含铁粉和羧酸的体系在吡啶水溶液中在氧气气氛下以令人惊奇的效率进行区域选择性氧化。微量硫化氢引发反应。
• Photogenerated Azido Radical Mediated Oxidation: Access to Carbonyl Functionality from Alcohols, Alkylarenes, and Olefins via Organophotoredox
  作者：Maniklal Shee、N. D. Pradeep Singh

  DOI：10.1002/adsc.202200242

  日期：2022.6.21

  Azido radical mediated photocatalytic oxidation method for the selective oxidation of various well-known feedstocks, such as (hetero)aromatic or aliphatic alcohols, alkylarenes, and terminal alkenes, is successfully accomplished. Herein, the catalytic HAT and reversible addition/elimination strategies of azido radical have been explored to convert the commonly oxidizable functionalities into invaluable

  叠氮自由基介导的光催化氧化方法用于选择性氧化各种众所周知的原料，如（杂）芳族或脂肪族醇、烷基芳烃和末端烯烃，已成功完成。在此，已经探索了催化 HAT 和叠氮自由基的可逆添加/消除策略，以使用有机光催化剂 4CzIPN 与四丁基叠氮化铵 (TBAN 3 ) 和空气/O 2将常见的可氧化官能团转化为宝贵的羰基或叔醇。作为氧化剂。事实上，这种温和、操作简单且高效的方法提供了良好至优异的产品产率，具有广泛的结构多样的底物，包括具有良好官能团耐受性的药物衍生物。已经进行了几个对照实验来研究详细的反应机理。
• A Mild and Efficient Flow Procedure for the Transfer Hydrogenation of Ketones and Aldehydes using Hydrous Zirconia
  作者：Claudio Battilocchio、Joel M. Hawkins、Steven V. Ley

  DOI：10.1021/ol400856g

  日期：2013.5.3

  A flow chemistry Meerwein-Ponndorf-Verley (MPV) reduction procedure using partially hydrated zirconium oxide via a machine-assisted approach is reported. The heterogeneous reductive system could be applied to a wide range of functionalized substrates, allowing clean and fast delivery of the alcohol products within a few minutes (6-75 min). In three examples the system was scaled to deliver 50 mmol of product.
• Chiral β-diketonate ligands of ‘pseudo planar chiral’ topology: enantioselective synthesis and transition metal complexation
  作者：Brian M. Bocknack、Long-Cheng Wang、Freddie W. Hughes、Michael J. Krische

  DOI：10.1016/j.tet.2005.03.118

  日期：2005.6

  A practical enantioselective synthesis of chiral beta-diketonate ligands 1a-1d, which are of 'pseudo planar-chiral' topology, is described. Additionally, the first chiral bis(diketonates) 2a-2c, ligands of C-2-symmetry that are isoelectronic with respect to related salen ligand systems, have been prepared. Protocols for the inetallation of ligands 1a-1d, 2b and 2c are reported. (c) 2005 Elsevier Ltd. All rights reserved.