threo-2-(1-Hydroxyethyl)cyclohexanone | 26343-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: threo-2-(1-Hydroxyethyl)cyclohexanone
• 英文别名: (2R)-2-[(1R)-1-hydroxyethyl]cyclohexan-1-one
• CAS: 26343-65-7
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: JPVZXEQZCYRRNC-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-氯-1-己醇 在 镍 pyridinium chloroformate 、 potassium tert-butylate 、 氢气 、 硼酸 、 异氰酸苯酯 、 三乙胺 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 83.75h， 生成 threo-2-(1-Hydroxyethyl)cyclohexanone
  参考文献：
  名称：

  .DELTA.2-异恶唑啉的减少。3. 雷尼镍催化β-羟基酮的形成

  摘要：

  确定最佳条件转化 d'isoxazolines-2 en β-hydroxycetones en utilisant un catalyseur Ni de Raney, l'acide borique, un melange 5/1 甲醇/eau et l'hydrogene Gazeux

  DOI：

  10.1021/ja00356a021

文献信息

• 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
  作者：Sergio Rossi、Tiziana Benincori、Laura Maria Raimondi、Maurizio Benaglia

  DOI：10.1055/s-0039-1690777

  日期：2020.4

  This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride)

  该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
• Novel stereocontrolled syntheses of exocyclic γ-oxovinyltrimethylsilanes. A potential route for stereodefined exocyclic tetrasubstituted alkenes
  作者：Kazuhiko Nakatani、Tomoko Izawa、Yoshihiko Odagaki、Sachihiko Isoe

  DOI：10.1039/c39930001365

  日期：——

  The course of the dehydration of α-hydroxy-γ-oxotrimethylsilanes is highly dependent on the conditions to produce stereoselectively (Z)- and (E)-γ-oxovinyltrirnethylsilanes, which are potential precursors for preparation of stereodefined exocyclic tetrasubstituted alkenes.

  δ-羟基-δ-氧代三甲基硅烷的脱水过程在很大程度上取决于生成立体选择性 (Z)- 和 (E)- δ-氧代乙烯基三irnethyl 硅烷的条件，这些硅烷是制备立体定义的外环四取代烯的潜在前体。
• Syntheses and Theoretical Studies of Exocyclic .gamma.-Oxoalkenyltrimethylsilanes. An Approach to the Stereodefined Exocyclic Tetrasubstituted Alkenes
  作者：Kazuhiko Nakatani、Tomoko Izawa、Sachihiko Isoe

  DOI：10.1021/jo00099a027

  日期：1994.10

  The Z-selectivity in the dehydration of alpha-hydroxy-gamma-oxoalkyltrimethylsilanes under acidic conditions was studied from experimental and theoretical points of view. Experimental results showed that (Z)-gamma-oxoalkenyltrimethylsilanes were thermodynamic products under these conditions. The dehydration studies of the compound involving the tert-butyl group instead of the TMS group pointed out that not only steric but also electronic effects of Si could contribute to the distribution of the products as well as their stereochemistries. Theoretical studies using ab initio calculation at the 6-31G* level indicated that the (Z)-isomer was thermodynamically more stable than the corresponding (E)-isomer. Detail examinations of the optimized structures showed that the configuration of Si in the (Z)-isomer was slightly distorted from tetrahedral. Interpretation of the geometrical change of Si to rationalization of the thermodynamic preference was discussed fi om the viewpoint of possible coordination of the carbonyl oxygen to Si. Those (Z)-gamma-oxoalkenyltrimethylsilanes would have potential to be the novel type of alkenylmetal compounds in organic synthesis as we demonstrated in the construction of stereodefined exocyclic tetrasubstituted alkene.
• Reduction of .DELTA.2-isoxazolines: a conceptually different approach to the formation of aldol adducts
  作者：Dennis P. Curran

  DOI：10.1021/ja00378a050

  日期：1982.7
• A Solution to the Cyclic Aldol Problem
  作者：Steven W. Baldwin、Ping Chen、Nikola Nikolic、Daniel C. Weinseimer

  DOI：10.1021/ol005525a

  日期：2000.5.1

  A protocol for achieving stereoselective aldol reactions with cyclic ketones is presented. In terms of yield, the process is particularly effective when a quaternary center at the alpha-carbon of the beta-hydroxy ketone product is created. The stereochemical outcome, anti or syn, is achieved by the Lewis acid-mediated ring expansion of stereochemically homogeneous epoxides in a reaction related to the pinacol rearrangement.