(S)-3-([1,1'-biphenyl]-4-yl)cyclohexanone | 1037238-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-([1,1'-biphenyl]-4-yl)cyclohexanone
• 英文别名: (S)-3-(4-phenylphenyl)cyclohexanone；(S)-3-([1,1'-biphenyl]-4-yl)cyclohexan-1-one；(S)-3-(biphenyl-4-yl)cyclohexanone；(3S)-3-(4-phenylphenyl)cyclohexan-1-one
• CAS: 1037238-05-3
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: PHMNEQQEHAHWCB-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 4-联苯硼酸 在 acetylacetonatobis(ethylene)rhodium(I) 、 (R)-BICMAP 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以93%的产率得到(S)-3-([1,1'-biphenyl]-4-yl)cyclohexanone
  参考文献：
  名称：

  手性二氢苯并呋喃基二膦（BICMAP）：光学拆分及其在铑（I）催化的芳基和烯基硼酸向环烯酮的不对称1,4-加成反应中的应用

  摘要：

  基于手性二氢苯并呋喃的二膦配体（BICMAP）1用作铑（I）催化的芳基硼酸不对称1,4-加成至环烯酮（ee高达99％ee）的配体。我们还发现，BICMAP-铑体系是一种有效的催化剂，用于以良好的对映选择性将烯基硼酸1，4-加成至2-环己烯酮。

  DOI：

  10.1016/j.tetlet.2012.06.064

文献信息

• Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions
  作者：Xiangqing Feng、Beibei Wei、Jing Yang、Haifeng Du

  DOI：10.1039/c1ob05971h

  日期：——

  One novel type of chiral olefin/sulfinimide hybrid ligands has been developed through a simple one-step condensation of α,β-unsaturated ketones with tert-butanesulfinamide and utilized successfully for rhodium-catalyzed asymmetric conjugated additions to furnish the desired adducts in high yields with excellent ee's.

  通过α，β-不饱和酮与化合物的简单一步缩合，已经开发出一种新型的手性烯烃/亚磺酰亚胺杂化配体 叔丁烷亚磺酰胺 并成功地用于铑催化的不对称共轭加成中，从而以优异的ee高收率提供所需的加合物。
• Chiral dihydrobenzofuran-based diphosphine (BICMAP): optical resolution and application to rhodium(I)-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to cyclic enones
  作者：Takashi Mino、Masatoshi Hashimoto、Katsunori Uehara、Yoshiaki Naruse、Shohei Kobayashi、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetlet.2012.06.064

  日期：2012.8

  Chiral dihydrobenzofuran-based diphosphine ligand (BICMAP) 1 was used as a ligand for the rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to cyclic enones up to 99% ee. We also found that the BICMAP-rhodium system was an efficient catalyst for the 1,4-addition of alkenylboronic acids to 2-cyclohexenone in good enantioselectivities.

  基于手性二氢苯并呋喃的二膦配体（BICMAP）1用作铑（I）催化的芳基硼酸不对称1,4-加成至环烯酮（ee高达99％ee）的配体。我们还发现，BICMAP-铑体系是一种有效的催化剂，用于以良好的对映选择性将烯基硼酸1，4-加成至2-环己烯酮。
• Enantio‐ and Diastereodivergent Synthesis of Spirocycles through Dual‐Metal‐Catalyzed [3+2] Annulation of 2‐Vinyloxiranes with Nucleophilic Dipoles
  作者：Youbin Peng、Xiaohong Huo、Yicong Luo、Liang Wu、Wanbin Zhang

  DOI：10.1002/anie.202111842

  日期：2021.11.15

  A dual-metal-catalyzed asymmetric [3+2] annulation of 2-vinyloxiranes with the challenging nucleophilic dipoles (imino esters) was achieved. It was successfully applied to the stereodivergent synthesis of structurally rigid spirocyclic framework. A series of spiro compounds bearing a pyrroline and an olefin were synthesized in an enantio- and diastereodivergent manner.

  实现了具有挑战性的亲核偶极子（亚氨基酯）的 2-乙烯基环氧乙烷的双金属催化不对称 [3+2] 环化。它成功地应用于结构刚性螺环骨架的立体发散合成。以对映和非对映发散方式合成了一系列带有吡咯啉和烯烃的螺环化合物。
• Three-Dimensional Homochiral Covalent Organic Frameworks with Intrinsic Chiral <b>qzd</b> Topology
  作者：Xing Kang、Cheng Cheng、Xu Chen、Jinqiao Dong、Yan Liu、Yong Cui

  DOI：10.1021/jacs.3c14230

  日期：2024.3.27

  framework materials have been reported, there are few examples known to combine molecular chirality, helicity, and three-dimensional (3D) intrinsically chiral topology in one structure, which is beneficial for chirality transfer and amplification. Here, we report the synthesis of the first two 3D covalent organic frameworks (COFs) with an intrinsic chiral qzd topology, which exhibit unusual integration of

  尽管已经报道了多种手性多孔骨架材料，但将分子手性、螺旋性和三维（3D）本质手性拓扑结合在一种结构中的例子很少，这有利于手性转移和放大。在这里，我们报告了前两个具有内在手性qzd拓扑结构的 3D 共价有机框架 (COF) 的合成，它们表现出各种同手性和同螺旋特征的不寻常整合。通过4-连接的卟啉四胺和2-连接的对映纯二烯二醛的亚胺缩合，我们制备了两种具有非互穿qzd拓扑结构的COF。 V 形二烯连接体的特定几何形状和构象灵活性控制具有旋转连接的方形平面卟啉单元的排列，并促进产生以卟啉螺旋排列为特征的同手性延伸多孔结构。 CCOF 23与 Rh(I) 的合成后金属化为芳基硼酸与 2-环己烯酮的不对称迈克尔加成反应提供了非均相催化剂，与均相对应物相比，其显示出更高的对映选择性，可能是由于螺旋通道的有限效应。这一发现将为探索多手性材料提供动力，为固态下螺旋性、同手性和对映选择性的生成和控制提供新的见解。
• Polymer-Incarcerated Chiral Rh/Ag Nanoparticles for Asymmetric 1,4-Addition Reactions of Arylboronic Acids to Enones: Remarkable Effects of Bimetallic Structure on Activity and Metal Leaching
  作者：Tomohiro Yasukawa、Hiroyuki Miyamura、Shu̅ Kobayashi

  DOI：10.1021/ja307913e

  日期：2012.10.17

  Robust and highly active bimetallic Rh nanoparticle (NP) catalysts, PI/CB Rh/Ag have been developed and applied to the asymmetric 1,4-addition of arylboronic acids to enones without leaching of the metals. We found that the structures of the bimetallic Rh/Ag catalysts and chiral ligands strongly affect their catalytic activity and the amount of metal leaching. PI/CB Rh/Ag could be recycled several times by simple operations while keeping high yields and excellent enantioselectivities. To show the versatility of the PI/CB Rh/Ag catalyst, a one-pot, oxidation-asymmetric 1,4-addition reaction of an allyl alcohol and an arylboronic acid was demonstrated by combining the PI/CB Rh/Ag catalyst with PI/CB Au as an aerobic oxidation catalyst.