1-ethyl-2-cyclohepten-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-ethyl-2-cyclohepten-1-ol
• 英文别名: 1-ethylcyclohept-2-en-1-ol
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: PIIIZQTXAAQNER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-ethylcycloheptene oxide 在 chiral bicyclic diamine 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 1-ethyl-2-cyclohepten-1-ol
  参考文献：
  名称：

  Kinetic resolution of racemic epoxides using a chiral diamine catalyst

  摘要：

  The kinetic resolution of a variety of racemic epoxides has been performed using a chiral bicyclic diamine ligand. Using 5 mol% of catalyst very high selectivity could be achieved; both epoxide and the corresponding allylic alcohol could be obtained in up to 99% ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.017

文献信息

• 1,4-Addition of Diorganozincs to<b><i>α</i></b>,<b><i>β</i></b>-Unsaturated Ketones Catalyzed by a Copper(I)-Sulfonamide Combined System
  作者：Masato Kitamura、Takashi Miki、Keiji Nakano、Ryoji Noyori

  DOI：10.1246/bcsj.73.999

  日期：2000.4

  A mixture of CuCN and N-benzylbenzenesulfonamide catalyzes the 1,4-addition of dialkylzincs or diarylzincs (Cu : Zn = 1 : 200 to 1 : 10000) to α,β-unsaturated ketones to give, after aqueous workup, the corresponding β-substituted ketones in nearly quantitative yields. A range of cyclic enones having s-cis or s-trans geometries as well as conformationally flexible acyclic enones are usable as substrates

  CuCN 和 N-苄基苯磺酰胺的混合物催化二烷基锌或二芳基锌（Cu : Zn = 1 : 200 至 1 : 10000）与 α,β-不饱和酮的 1,4-加成反应，在水处理后得到相应的 β-以接近定量的产率取代酮。一系列具有 s-cis 或 s-trans 几何结构的环状烯酮以及构象灵活的无环烯酮可用作底物。乙基比甲基和苯基更容易迁移。CuOTf、CuO-t-C4H9 和甲基铜可用于代替 CuCN。在水处理之前，原位形成的烷基烯醇锌进一步与醛发生醇醛反应或 Pd(0) 辅助与乙酸烯丙酯偶联，产生区域控制的邻位碳缩合产物。
• Chiral phosphine–phosphite ligands in the enantioselective 1,4-addition of Grignard reagents to α,β-unsaturated carbonyl compounds
  作者：Qaseem Naeemi、Tobias Robert、Darius P. Kranz、Janna Velder、Hans-Günther Schmalz

  DOI：10.1016/j.tetasy.2011.04.018

  日期：2011.4

  phosphine–phosphite ligands was evaluated in the Cu-catalyzed asymmetric 1,4-addition of Grignard reagents to cyclopentenone, cycloheptenone and 5,6-dihydro-2H-pyran-2-one. TADDOL-based ligands 1a and 1b with a bulky substituent at the ortho-position to the chiral phosphite moiety gave rise to the 1,4-addition products with high enantioselectivities (up to 93% ee). In addition to ethyl-MgBr (as a standard

  在铜催化的格氏试剂对环戊烯酮，环庚烯酮和5,6-二氢-2 H-吡喃-2-酮的不对称1,4-加成反应中，评估了手性膦-亚磷酸酯配体库。在手性亚磷酸酯部分的邻位具有大取代基的基于TADDOL的配体1a和1b产生具有高对映选择性（至多93％ee）的1，4-加成产物。除了乙基-MgBr（作为标准的烷基亲核试剂）之外，还可以使用苯基-和异丙烯基-MgBr。就环戊烯酮而言，使用氯三甲基硅烷作为添加剂可提高区域选择性和对映选择性。
• Copper-catalyzed asymmetric conjugate addition with Grignard reagents and SimplePhos ligands
  作者：Laëtitia Palais、Alexandre Alexakis

  DOI：10.1016/j.tetasy.2009.11.016

  日期：2009.12

  Herein we report the copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic and acyclic enones, with SimplePhos as chiral ligands. A variety of Grignard reagents can be added to a range of cyclic and acyclic enones, with moderate to good enantioselectivities (ee’s up to 86%).

  在本文中，我们报道了将格利雅试剂的铜催化不对称共轭加成到环状和非环状烯酮上，其中SimplePhos为手性配体。可以将各种格氏试剂添加到一系列环状和非环状烯酮中，具有中等到良好的对映选择性（ee高达86％）。
• Methylene-Bridged P-Chiral Diphosphines in Highly Enantioselective Reactions
  作者：Yoshinori Yamanoi、Tsuneo Imamoto

  DOI：10.1021/jo990131m

  日期：1999.4.1
• Kinetic resolution of racemic epoxides using a chiral diamine catalyst
  作者：Arnaud Gayet、Pher G. Andersson

  DOI：10.1016/j.tetlet.2005.05.017

  日期：2005.7

  The kinetic resolution of a variety of racemic epoxides has been performed using a chiral bicyclic diamine ligand. Using 5 mol% of catalyst very high selectivity could be achieved; both epoxide and the corresponding allylic alcohol could be obtained in up to 99% ee. (c) 2005 Elsevier Ltd. All rights reserved.