(S)-2-phenylcyclooctanone | 1278594-25-4

• 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)-2-phenylcyclooctanone
• 英文别名: 2-phenylcyclooctanone；(2S)-2-phenylcyclooctan-1-one
• CAS: 1278594-25-4
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: QXBUAHVMLOQNTG-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-2-phenylcyclooctanone 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 红铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (S)-((1S,2S)-2-phenylcyclooctyl)-α-acetyl mandelate
  参考文献：
  名称：

  An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion

  摘要：

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.

  DOI：

  10.1021/ol200402m
• 作为产物：
  描述：

  苯甲醛腙 在 草酰氯 、 (3aR,3a'R,3a''R,8aS,8a'S,8a''S)-2,2',2''-(propane-1,2,2-triyl)tris(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 、 二甲基亚砜 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-2-phenylcyclooctanone
  参考文献：
  名称：

  An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion

  摘要：

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.

  DOI：

  10.1021/ol200402m

文献信息

• 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。
• Highly Efficient and Enantioselective α-Arylation of Cycloalkanones by Scandium-Catalyzed Diazoalkane-Carbonyl Homologation
  作者：Jason Kingsbury、Victor Rendina、Hilan Kaplan

  DOI：10.1055/s-0031-1289650

  日期：2012.3

  Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazo­alkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98:2 er and >98% yield. The formal C-C insertion of aryldiazo­methanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of α-arylation.

  功能化的α-叔和α-季2-芳基环烷酮通过三氟甲磺酸钪(III)催化的重氮甲烷-羰基同系化反应迅速获得。最近的进展使得碳插入反应能够在催化剂负载量低至0.5 mol%的情况下进行，规模可达5 mmol。结合易于获得的基于双和三噁唑啉的配体与三氟甲磺酸钪，可以合成具有高达98:2 对映体比和>98%产率的芳基化中环碳环。芳基重氮甲烷在无取代环烷酮中的正式C-C插入提供了一种一步解决α-芳基化持续挑战的方法。
• An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion
  作者：Victor L. Rendina、David C. Moebius、Jason S. Kingsbury

  DOI：10.1021/ol200402m

  日期：2011.4.15

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.