cis-ethyl 2-hydroxy-cyclohexanoate | 1655-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-ethyl 2-hydroxy-cyclohexanoate
• 英文别名: rac-ethyl (1R,2S)-2-hydroxycyclohexanecarboxylate；rac-cis 1-ethoxycarbonyl-2-hydroxy-cyclohexane；ethyl cis-2-hydroxy-1-cyclohexane carboxylate；ethyl-cis-2-hydroxy-1-cyclohexanecarboxylate；cis-ethyl 2-hydroxycyclohexanecarboxylate；ethyl 2-hydroxycyclohexanecarboxylate；2-Hydroxy-cyclohexanecarboxylic acid ethyl ester, cis；ethyl (1S,2R)-2-hydroxycyclohexane-1-carboxylate
• CAS: 1655-06-7；3444-72-2；6125-55-9；6149-52-6；29569-79-7；61586-78-5；77026-73-4；119068-36-9；119068-37-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: WOGRTPJVNNCUKN-JGVFFNPUSA-N

物化性质

• 保留指数：
  1263

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-ethyl 2-hydroxy-cyclohexanoate 在 ammonium hydroxide 作用下， 生成 cis-2-aminocyclohexanecarboxylic acid amide
  参考文献：
  名称：

  STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. X. SYNTHESIS OF SIMPLE HYDROXYLATED β-SUBSTITUTED Δ^α,β-BUTENOLIDES

  摘要：

  DOI：

  10.1021/jo01199a008
• 作为产物：
  描述：

  水杨酸乙酯 在 乙醇 、 镍 作用下， 190.0 ℃ 、17.16 MPa 条件下， 生成 cis-ethyl 2-hydroxy-cyclohexanoate
  参考文献：
  名称：

  STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. X. SYNTHESIS OF SIMPLE HYDROXYLATED β-SUBSTITUTED Δ^α,β-BUTENOLIDES

  摘要：

  DOI：

  10.1021/jo01199a008

文献信息

• 14-Membered cyclodepsipeptides with alternating β-hydroxy and α-amino acids by cyclodimerization
  作者：Boyan Iliev、Anthony Linden、Roland Kunz、Heinz Heimgartner

  DOI：10.1016/j.tet.2005.11.002

  日期：2006.2

  cyclodimer 10. In all cases, when starting with racemic material, only the trans-substituted cyclodepsipeptides were isolated. Simple molecular modeling revealed that the formation of the cyclodimer is thermodynamically slightly more favorable than that of the cyclomonomer. The proposal that cyclodimer formation is preferred because of the presence of intramolecular H-bonds could not be confirmed by X-ray

  描述了在“直接酰胺环化”（DAC）条件下1型β-羟基酰胺的环二聚（孪生）。尽管其他偶联方法也可得出中等结果，但通过DAC可获得最佳收率，环二聚体10可达88％。在所有情况下，当从外消旋物质开始时，仅分离出反式取代的环二肽。简单的分子模型表明，环二聚体的形成在热力学上比环聚单体的形成稍微更有利。由于分子内氢键的存在，优选形成环二聚体的提议不能通过X射线晶体学证实。还研究了取代基在氨基酸和羟基酸部分中的影响。结果表明，仅当羟基酸部分被α，α-二取代时，环二聚作用才成功。
• A Noncoordinating Acid–Base Catalyst for the Mild and Nonreversible <i>tert</i>-Butylation of Alcohols and Phenols
  作者：Keith R. Fandrick、Nitinchandra D. Patel、Suttipol Radomkit、Arindom Chatterjee、Stefan Braith、Daniel R. Fandrick、Carl A. Busacca、Chris H. Senanayake

  DOI：10.1021/acs.joc.1c00193

  日期：2021.3.19

  A mild and nonreversible tert-butylation of alcohols and phenols can be achieved in high yields using the noncoordinating acid–base catalyst [bis(trifluoromethane)sulfonimide and 2,6-lutidine] with a tert-butylation reagent, tert-butyl 2,2,2-trichloroacetimidate. This method allows the use of substrates containing acid sensitive groups such as ketal, Boc, and boronate esters.

  温和和不可逆的叔醇和酚的-butylation可以以高产率使用非配位酸-碱催化剂[双（三氟甲烷）磺酰亚胺和2,6-二甲基吡啶]用来实现叔-butylation试剂，叔丁基2,2- ，2-三氯乙亚胺酸酯。该方法允许使用包含酸敏感基团的底物，例如缩酮，Boc和硼酸酯。
• Synthesis of a New Class of Chiral 1,5-Diphosphanylferrocene Ligands and Their Use in Enantioselective Hydrogenation
  作者：Tania Ireland、Katja Tappe、Gabi Grossheimann、Paul Knochel

  DOI：10.1002/1521-3765(20020215)8:4<843::aid-chem843>3.0.co;2-9

  日期：2002.2.15

  A new family of ferrocenylphosphane ligands has been prepared. Their flexible synthesis allows many structural modifications. The asymmetric induction of these ligands was examined in the hydrogenation of functionalized C=C, C=O, and C=N bonds. The enantioselectivity of the reaction was strongly dependent on the substituent R at the position alpha to the ferrocene moiety. In many cases, both enantiomeric

  制备了新的二茂铁基膦配体家族。它们的灵活合成可以进行许多结构修饰。在官能化的C = C，C = O和C = N键的氢化中检查了这些配体的不对称诱导。反应的对映选择性强烈取决于二茂铁部分α位的取代基R。在许多情况下，还原产物的两种对映体β-羟基酯都可以通过简单地用甲基取代配体中的二甲基氨基来获得。
• Enantioselective ketoester reductions in water: a comparison between microorganism- and ruthenium-catalyzed reactions
  作者：Saoussen Zeror、Jacqueline Collin、Jean-Claude Fiaud、Louisa Aribi Zouioueche

  DOI：10.1016/j.tetasy.2010.05.014

  日期：2010.5

  search for green chemistry methods for the enantioselective reduction of ketoesters Saccharomyces cerevisiae- and ruthenium-catalyzed reactions in water have been investigated. The highest enantiomeric excesses for the reduction of α- and β-ketoesters have been obtained by S. cerevisiae. Chiral ruthenium catalysts are active for the reduction of all ketoesters with low to moderate enantioselectivities

  在寻找绿色化学方法以对映体还原酮酸酯的过程中，已经研究了酿酒酵母和钌催化的水中反应。酿酒酵母获得了用于还原α-和β-酮酸酯的最高对映体过量。手性钌催化剂对于还原所有酮酯具有低到中等对映选择性的活性，这取决于底物和配体的性质。有趣的是，对于几种底物，已经根据催化方法或配体的结构获得了羟基酯的两种对映体。
• Synthesis and Characterization of the Enantiomerically Pure<i>cis</i>- and<i>trans</i>-2,4-Dioxa-3-fluoro-3-phosphadecalins as Inhibitors of Acetylcholinesterase
  作者：Michael Wächter、Peter Rüedi

  DOI：10.1002/cbdv.200800335

  日期：2009.3

  The title compounds, the P(3)-axially- and P(3)-equatorially-substituted cis- and trans-configured 3-fluoro-2,4-dioxa-3-phosphadecalin 3-oxides (=3-fluoro-2,4-dioxa-3-phosphabicyclo[4.4.0]decane 3-oxides) have been prepared (ee>99%) and fully characterized. The compounds are irreversible inhibitors of acetylcholinesterase, and both the kinetic data and the mechanisms of the inhibition are determined

  标题化合物，P（3）-轴向和P（3）-赤道取代的顺式和反式3-氟-2,4-二氧杂-3-磷酸钙素3-氧化物（= 3-氟-2已经制备了（4-二氧杂-3-磷酸双环[4.4.0]癸烷3-氧化物）（ee＞ 99％）并进行了充分表征。该化合物是乙酰胆碱酯酶的不可逆抑制剂，其动力学数据和抑制机理均由先前报告中所述的新型酶动力学方法确定。抑制剂表现出明显的立体选择性，并且其中几种比通常用作有效标准品的氟磷酸二异丙酯明显更强。