(-)-fenchone

• 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: (-)-fenchone
• 英文别名: (1R)-(-)-fenchone；L-fenchone；(R)-Fenchone; L-(-)-Fenchone; L-Fenchone; l-Fenchone；(1R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: LHXDLQBQYFFVNW-OMNKOJBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  (-)-fenchone 在 Ni(1,3-bis(3,5-di-tert-butylphenyl)imidazolidin-2-yl)(phenyl methacrylate)2 、 三苯基硅烷 作用下， 反应 6.0h， 以99%的产率得到triphenyl(1,3,3-trimethylbicyclo[2.2.1]heptan-2-yloxy)silane
  参考文献：
  名称：

  [EN] NI(0) CATALYSTS
  [FR] CATALYSEURS NI(0)

  摘要：

  提供于此的镍(0)催化剂在暴露于空气时稳定，并且可用于催化形成C-C、C-O或C-N键。

  公开号：

  WO2017059181A1

文献信息

• Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
  作者：Georgi M. Dobrikov、Irena Philipova、Rositsa Nikolova、Boris Shivachev、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.poly.2012.06.090

  日期：2012.9

  were prepared and added to chiral bicyclic ketones (1R-(+)-camphor analogue 2 and 1R-(−)-fenchone 3), resulting in the preparation of a small “library” of chiral aminoalcohols able to serve as ligands in metal mediated asymmetric synthesis. The configuration of the chiral ligands was approved by applying advanced NMR experiments. The absolute configurations of 1,2-disubstituted planar chiral ferrocene-based

  摘要制备了一系列功能化的有机锂化合物，并将其添加到手性双环酮（1R-（+）-樟脑类似物2和1R-（--- fenchone 3）中，从而制备了一个小的“手性”氨基醇醇“库”在金属介导的不对称合成中用作配体。手性配体的构型通过应用先进的NMR实验得到了认可。通过NMR实验确定1，2-二取代的平面手性二茂铁基氨基醇15、18和19的绝对构型，并通过X射线晶体学证实。测试了新的手性配体作为向苯甲醛中添加二乙基锌的预催化剂。反应以优异的转化率和中等程度的对映选择性进行。
• Selective Cross‐Coupling of Unsaturated Substrates on Al ^I
  作者：Anton Dmitrienko、Melanie Pilkington、Georgii I. Nikonov

  DOI：10.1002/chem.202004907

  日期：2021.3.26

  CH‐acidic ketone (1R)‐(+) camphor, the reaction affords a hydrido alkoxide compound of Al, formed as the result of enolization, whereas an enolizable imine, (1‐phenylethylidene)aniline, and the bulky ketone isophorone, still chemoselectively couple with pyridine. In contrast, reaction with the ester p‐tolyl benzoate results in cleavage of the ester bond together with replacement of the alkoxy group by

  Al I化合物NacNacAl（1，NacNac = [ArNC（Me）CHC（Me）NAr] -，Ar = 2,6 - i Pr 2 C 6 H 3）用作羰基（二苯甲酮， Fenchone，异佛尔酮，对甲苯基苯甲酸酯，N，N-二甲基苯甲酰胺，（1-苯乙叉基）苯胺）和吡啶。使用CH酸性酮（1 R）（+）樟脑，反应生成烯醇化反应形成的Al氢羟基醇盐化合物，而可烯化的亚胺（1-苯乙叉基）苯胺和庞大的酮异佛尔酮仍与吡啶进行化学选择性偶联。相反，与酯对甲苯基苯甲酸酯的反应导致酯键的断裂以及烷氧基被吡啶部分的氢原子取代。这项研究表明，对于设有苯基取代基，通过η的中间形成反应进行羰基片2（C，X）配位的（X = O，N）羰基的加合物，而反应1与（ř）-（-）-甲酮在没有吡啶的情况下导致NacNac配体的Ar取代基的侧基异丙基中的CH活化。
• Wolf, Gerhard; Wuerthwein, Ernst-Ulrich, Chemische Berichte, 1991, vol. 124, # 3, p. 655 - 663
  作者：Wolf, Gerhard、Wuerthwein, Ernst-Ulrich

  DOI：——

  日期：——
• Optically active ketones as chiral auxiliaries in the [2,3]-Wittig rearrangement
  作者：David S. Keegan、M. Mark Midland、Ralph T. Werley、Jim I. McLoughlin

  DOI：10.1021/jo00003a048

  日期：1991.2

  The stereochemical aspects of the [2,3]-Wittig rearrangement of optically active tertiary allyl ethers derived from (+)-camphor and (-)-fenchone were investigated. The rearrangement of the (+)-camphor derivative yielded two olefin products in a 70/30 E/Z ratio. The geometry of the trisubstituted olefin produced during the rearrangement was assigned by NOE experiments. The configuration of the newly formed carbinol center of the products was established by kinetic resolution, Mosher's method, and conversion to derivatives of known absolute configuration. The absolute configuration of the carbinol center for the Z isomer was assigned to be S and that of the E isomer to be R. The (-)-fenchone derivative gave only a single Z olefin product, which was assigned the S configuration at the carbinol center.
• US6287829B1
  申请人：——

  公开号：US6287829B1

  公开（公告）日：2001-09-11