(1S)-endo-bornyl vinyl ether | 80124-60-3

• 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: (1S)-endo-bornyl vinyl ether
• 英文别名: (1S,2R,4S)-2-ethenoxy-1,7,7-trimethylbicyclo[2.2.1]heptane
• CAS: 80124-60-3
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: LQLLNKLOYCYFEB-HOSYDEDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-氧代-4-苯基-3-丁酸甲酯 、 (1S)-endo-bornyl vinyl ether 在 Eu(fod)3 作用下， 以 正己烷 为溶剂， 反应 72.0h， 以95%的产率得到(4S,6S)-4-Phenyl-6-((1S,2R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthèse asymétrique et configuration absolue de dihydropyranes substitués, par hétérocycloaddition intermoléculaire d'éthers vinyliques chiraux

  摘要：

  The alkyl vinyl ethers 2b-8b (deriving from the alcohols 2a-8a) smoothly reacted with methyl E-benzylidenepyruvate 10 in the presence of catalytic amounts of Eu(fod)(3) or Yb(fod)(3) in refluxing hexane, thus leading to the dihydropyran endo adducts 13-19 in high yields (80-95%). The endo-cycloadducts 13-17 were obtained with diastereofacial selectivities (ds) ranging from 76/24 to 87.5/12.5. Asymmetric induction was found to culminate with the vinyl ether (-)-7b deriving from n-butyl (R)-(-)-mandelate : the best ds (92.5/7.5) was obtained for the corresponding adduct 18 after 6 days at room temperature. The absolute configurations of the major isomers of the dihydropyrans 16-18, 20 and 21 were established by oxydative degradation to optically active alpha-phenylsuccinic acid derivatives.

  DOI：

  10.1016/s0040-4020(01)85370-9
• 作为产物：
  描述：

  冰片 在 sodium amalgam 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 正己烷 为溶剂， 生成 (1S)-endo-bornyl vinyl ether
  参考文献：
  名称：

  A New Convenient Synthesis of Ethenyl Ethers

  摘要：

  醇对1,2-双(苯磺酰基)乙烯的加成-消除反应得到β-烷氧基乙烯基砜，再通过6%的钠汞齐进行还原消除，以高产率和高纯度生成相应的乙烯基醚。

  DOI：

  10.1055/s-2001-18757

文献信息

• Two Types of Cross-Coupling Reactions between Electron-Rich and Electron-Deficient Alkenes Assisted by Nucleophilic Addition Using an Organic Photoredox Catalyst
  作者：Yosuke Tanaka、Suzuka Kubosaki、Kazuyuki Osaka、Mugen Yamawaki、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/acs.joc.8b02025

  日期：2018.11.16

  Two types of photoreactions between electronically differentiated donor and acceptor alkenes assisted by nucleophilic addition using an organic photoredox catalyst efficiently afforded 1:1 or 2:1 cross-coupling adducts. A variety of alkenes and alcohols were employed in the photoreaction. Control of the reaction pathway (i.e., the formation of the 1:1 or 2:1 adduct) was achieved by varying the concentration

  通过使用有机光氧化还原催化剂的亲核加成辅助，电子分化的供体和受体烯烃之间的两种类型的光反应有效地提供了1：1或2：1的交叉偶联加合物。在光反应中使用了各种烯烃和醇。通过改变所用醇的浓度，可以控制反应路径（即形成1：1或2：1加合物）。详细的机理研究表明，有机光氧化还原催化剂可作为有效的电子介体，促进交叉偶联加合物的形成。
• Access to α-Amino Acid Esters through Palladium-Catalyzed Oxidative Amination of Vinyl Ethers with Hydrogen Peroxide as the Oxidant and Oxygen Source
  作者：Lu Ouyang、Jianxiao Li、Jia Zheng、Jiuzhong Huang、Chaorong Qi、Wanqing Wu、Huanfeng Jiang

  DOI：10.1002/anie.201709285

  日期：2017.12.11

  A novel and convenient palladium catalytic system for the synthesis of α‐amino acid esters from simple starting materials is reported. Hydrogen peroxide not only acts as the green oxidant, but also as the oxygen source. This strategy for the conversion of amines and vinyl ethers into highly functionalized and structurally diverse α‐amino acid esters is characterized by the simplicity of the experimental

  报道了一种新颖且方便的钯催化体系，可从简单的起始原料合成α-氨基酸酯。过氧化氢不仅充当绿色氧化剂，而且充当氧气源。这种将胺和乙烯基醚转化为高度官能化和结构多样的α-氨基酸酯的策略的特点是实验过程简单，反应条件温和，原子经济性高，可扩展性和实用性强。
• Boa, Andrew N.; Dawkins, David A.; Hergueta, Antonio R., Journal of the Chemical Society. Perkin transactions I, 1994, # 8, p. 953 - 960
  作者：Boa, Andrew N.、Dawkins, David A.、Hergueta, Antonio R.、Jenkins, Paul R.

  DOI：——

  日期：——
• Boa Andrew N., Dawkins David A., Hergueta Antonio R., Jenkins Paul R., J. Chem. Soc. Perkin Trans. 1, (1994) N 8, S 953-960
  作者：Boa Andrew N., Dawkins David A., Hergueta Antonio R., Jenkins Paul R.

  DOI：——

  日期：——