(S)-2-(2-methoxyphenyl)cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-(2-methoxyphenyl)cyclohexanone
• 英文别名: (S)-2-(o-anisyl)cyclohexanone；(2S)-2-(2-methoxyphenyl)cyclohexan-1-one
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: RBQAWPVPHCHEHE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三氟甲磺酸2-甲氧基苯基酯 、 1-tri(n-butyl)stannyloxy-1-cyclohexene 在 (R)-N-isopropyl-2-(dicyclohexylphosphino)-2'-(3-aminophenoxy)-1,1'-binaphthyl 、 sodium acetate 、 palladium diacetate 作用下， 以 乙醚 、 十二烷 为溶剂， 反应 72.17h， 以96%的产率得到(S)-2-(2-methoxyphenyl)cyclohexanone
  参考文献：
  名称：

  Arene CH ？O氢键：钯催化的酮化和乙烯基化中的立体控制工具

  摘要：

  弱是有力：对于锡烯醇化物的芳基化，在弱CH钯催化剂接合 O氢键键合到控制立体选择性（参见方案）。能够进行NHO氢键键合的类似催化剂也能很好地工作。

  DOI：

  10.1002/anie.201300621

文献信息

• A Brønsted Acid Catalyst for the Enantioselective Protonation Reaction
  作者：Cheol Hong Cheon、Hisashi Yamamoto

  DOI：10.1021/ja8041542

  日期：2008.7.1

  A highly reactive and robust chiral Brønsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Brønsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Brønsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity.

  开发了一种高反应性和稳健的手性布朗斯台德酸催化剂，手性 N-三氟甲磺酸硫代磷酰胺。使用这种手性布朗斯台德酸催化剂证明了第一个无金属布朗斯台德酸催化的甲硅烷基烯醇醚的对映选择性质子化反应。催化剂负载量可以降低到 0.05 mol%，而对对映选择性没有任何不利影响。
• Development of a new Lewis base-tolerant chiral LBA and its application to catalytic asymmetric protonation reaction
  作者：Cheol Hong Cheon、Tatsushi Imahori、Hisashi Yamamoto

  DOI：10.1039/c0cc02492a

  日期：——

  A new Lewis base-tolerant LBA (Lewis Acid Assisted Bronsted Acid) derived from La(OTf)(3) and (S)-HOP has been developed as a new chiral Bronsted acid. This acid has been successfully applied as a catalyst to asymmetric protonation reactions of silyl enol ethers of 2-substituted cyclic ketones.

  衍生自 La(OTf)(3) 和 (S)-HOP 的新型耐路易斯碱 LBA（路易斯酸辅助布朗斯台德酸）已被开发为一种新型手性布朗斯台德酸。该酸已成功用作 2-取代环酮的甲硅烷基烯醇醚不对称质子化反应的催化剂。
• [EN] PALLADIUM-CATALYZED ASYMMETRIC (HETERO)ARYLATION AND VINYLATION OF KETONE ENOLATES TO PRODUCE TERTIARY STEREOCENTERS AT ALPHA(α)-POSITION<br/>[FR] (HÉTÉRO)ARYLATION ET VINYLATION ASYMÉTRIQUES D'ÉNOLATES DE CÉTONES CATALYSÉES AU PALLADIUM PERMETTANT DE PRODUIRE DES STÉRÉOCENTRES TERTIAIRES EN POSITION ALPHA(&Agr;)
  申请人：NANAYNG TECHNOLOGICAL UNIVERSITY

  公开号：WO2014109712A1

  公开（公告）日：2014-07-17

  The invention relates to new ligands that are used in a palladium source catalyst system and in palladium catalyzed method for asymmetric α-(hetero)arylation and a-vinylation of ketones. The invention further relates to a process for preparing an asymmetric α-(hetero)arylated or a-vinylated ketone which comprises reacting the tin enolate of the ketone in the presence of catalyst system comprising a ligand of the invention and palladium source. By means of the ligands and process of the invention a stereogenic center in position a of the ketone is established with high enantiomeric excess.
• Arene CHO Hydrogen Bonding: A Stereocontrolling Tool in Palladium-Catalyzed Arylation and Vinylation of Ketones
  作者：Zhiyan Huang、Li Hui Lim、Zuliang Chen、Yongxin Li、Feng Zhou、Haibin Su、Jianrong Steve Zhou

  DOI：10.1002/anie.201300621

  日期：2013.4.26

  Weak is powerful: For the arylation of tin enolates, the palladium catalyst engages in weak CHO hydrogen bonds to control stereoselectivity (see scheme). Similar catalysts capable of NHO hydrogen bonding also works well.

  弱是有力：对于锡烯醇化物的芳基化，在弱CH钯催化剂接合 O氢键键合到控制立体选择性（参见方案）。能够进行NHO氢键键合的类似催化剂也能很好地工作。