ethyl 2-oxocyclodecane-1-carboxylate | 4017-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-oxocyclodecane-1-carboxylate
• 英文别名: 2-Oxo-cyclodecan-1-carbonsaeure-aethylester；Ethyl 2-oxocyclodecanecarboxylate
• CAS: 4017-58-7
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: VBWUFKFOEMFRHF-UHFFFAOYSA-N

物化性质

• 沸点：
  84-87 °C
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-oxocyclodecane-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 生成 2-Hydroxy-methylcyclodecanol
  参考文献：
  名称：

  Photoisomerizations of cis- and trans-3-methylenecyclodecene

  摘要：

  DOI：

  10.1021/ja00728a026
• 作为产物：
  描述：

  环辛酮 在 三氟化硼乙醚 作用下， 以 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 48.5h， 生成 ethyl 2-oxocyclodecane-1-carboxylate
  参考文献：
  名称：

  内酰胺连续扩环合成环肽模拟物

  摘要：

  据报道，有连续的扩环方案可以将天然和非天然氨基酸片段控制插入内酰胺中。可以通过操作简单且可扩展的迭代程序将氨基酸安装到大环化合物中，而无需进行高稀释。预期该方法具有广泛的用途，特别是对于合成具有医学重要性的环状肽模拟物而言。

  DOI：

  10.1002/chem.201703316

文献信息

• The preparation and spectral studies of a series of cyclic β-ketoesters
  作者：Sara Jane Rhoads、J.C. Gilbert、A.W. Decora、T.R. Garland、R.J. Spangler、Mary Jane Urbigkit

  DOI：10.1016/s0040-4020(01)99237-3

  日期：1963.1

  their C-methyl derivatives have been prepared and studied in the U.V. and I.R. spectral regions. The enolizable β-ketoesters show a high intensity K band in the 255–263 mμ region associated with the chelated enolic species and two pairs of bands in the 6 μ double bond stretching region which correspond to the structural features of the keto and enol tautomers. The non-enolizable β-ketoesters show only a

  在紫外和红外光谱范围内，已经制备并研究了环大小为5-12和15的2-甲氧基环烷酮及其C-甲基衍生物。可烯化的β-酮酸酯在255-263mμ的区域中显示出与螯合的烯醇式物种相关的高强度K谱带，在6μ双键拉伸区域中的两对谱带对应于酮和烯醇互变异构体的结构特征。不可烯化的β-酮酸酯在280-300mμ区域仅显示低强度R谱带，而在6μ区域仅显示一对谱带。光谱性质与烯醇含量和环系统的结构特征有关。螯合烯醇的特征IR频率的趋势已经被注意到并根据螯合结构的几何形状进行了解释。
• Structure-Activity Relationship for the First-in-Class Clinical Steroid Sulfatase Inhibitor Irosustat (STX64, BN83495)
  作者：L. W. Lawrence Woo、Dharshini Ganeshapillai、Mark P. Thomas、Oliver B. Sutcliffe、Bindu Malini、Mary F. Mahon、Atul Purohit、Barry V. L. Potter

  DOI：10.1002/cmdc.201100288

  日期：2011.11.4

  Structure–activity relationship studies were conducted on Irosustat (STX64, BN83495), the first steroid sulfatase (STS) inhibitor to enter diverse clinical trials for patients with advanced hormone‐dependent cancer. The size of its aliphatic ring was expanded; its sulfamate group was N,N‐dimethylated, relocated to another position and flanked by an adjacent methoxy group; and series of quinolin‐2(1H)‐one

  对 Irosustat (STX64, ​​BN83495) 进行了结构-活性关系研究，Irosustat 是第一个进入针对晚期激素依赖性癌症患者的多种临床试验的类固醇硫酸酯酶 (STS) 抑制剂。其脂肪环尺寸扩大；其氨基磺酸基团被 N,N-二甲基化，重新定位到另一个位置，并且两侧是相邻的甲氧基；并探索了一系列喹啉-2(1H ) -酮和伊罗司他的喹啉衍生物。在 JEG-3 细胞制剂中评估了合成化合物的 STS 抑制活性。将脂肪环从 7 个成员逐步扩大到 11 个成员会增加效力，尽管环尺寸的进一步增加是有害的。最好的体外 STS 抑制剂的 IC 50值在 0.015 至 0.025 nM之间。对 Irosustat 进行的其他修改被发现会消除或显着削弱其活性。分离了 Irosustat 与N , N-二甲基甲酰胺 (DMF)的偶氮甲碱加合物，并测定了 Irosustat 和该加合物的晶体结构。进行对接研究以探索化合物与
• Evaluating the Viability of Successive Ring‐Expansions Based on Amino Acid and Hydroxyacid Side‐Chain Insertion
  作者：Aggie Lawer、Ryan G. Epton、Thomas C. Stephens、Kleopas Y. Palate、Mahendar Lodi、Emilie Marotte、Katie J. Lamb、Jade K. Sangha、Jason M. Lynam、William P. Unsworth

  DOI：10.1002/chem.202002164

  日期：2020.10

  size. This manuscript, which builds upon our previous work on Successive Ring Expansion (SuRE) methods, details efforts to better define the scope and limitations of these reactions on lactam and β‐ketoester ring systems with respect to ring size and additional functionality. The synthetic results provide clear guidelines as to which substrate classes are more likely to be successful and are supported

  基于氨基/羟基酸侧链插入的扩环反应的结果很大程度上取决于环的大小。这份手稿建立在我们之前关于连续环扩展 (SuRE) 方法的工作的基础上，详细介绍了为更好地定义内酰胺和 β-酮酯环系统上这些反应在环大小和附加功能方面的范围和局限性所做的努力。合成结果为哪些底物类别更有可能成功提供了明确的指导，并得到了使用密度泛函理论 (DFT) 方法的计算结果的支持。计算扩环过程中可逆形成的三种异构体的相对吉布斯自由能，使得在大多数情况下能够正确预测新合成反应的可行性。新的合成和计算结果预计将支持新的基于内酰胺和β-酮酯的扩环反应的设计。
• Determination of tautomeric phenotypes of β-thioxo esters and characterization of the tautomeric enethiolic constituents by means of13C NMR spectroscopy
  作者：F. Duus、P. E. Hansen

  DOI：10.1002/mrc.1270220105

  日期：1984.1

  AbstractThe 13C NMR spectra of 28 enethiolizable β‐thioxo esters and 6 enethiolizable β‐thioxo thioloesters have been recorded in order to establish the tautomeric phenotypes of these compounds. All compounds investigated are essentially enethiolic. The carbonyl‐conjugated (Z)‐enethiol form is the exclusive or predominant tautomer of open‐chain β‐thioxo esters and thioloesters, thioacylmalonates and medium‐sized 2‐alkoxycarbonylcycloalkanethiones. The carbonyl‐conjugated (E)‐enethiol form is identifiable for open‐chain α‐unsubstituted β‐thioxo esters and thioloesters, and abundant for open‐chain α‐substituted β‐thioxo esters. Non‐conjugated enethiol forms [i.e. (Z)‐ and (E)‐isomeric β,γ‐unsaturated β‐mercapto esters] are abundant tautomeric constituents of ω‐substituted and higher 2‐alkoxycarbonylcycloalkanethiones. The chemical shifts of the carbon atoms directly involved in the tautomeric change have been rationalized in terms of substituent screening contributions. Deuterium isotope effects on the central carbon atoms of selected deuterio‐enethiolic compounds have been measured in order to depict the ester group rotamerism in CO‐conjugated (Z)‐enethiols. The abundance of the CO‐conjugated (E)‐enethiols, as well as the preferred population of the non‐conjugated (Z)‐enethiol form relative to the non‐conjugated (E)‐enethiol form, is rationalized in terms of the occurrence of a no‐bond interaction between the lone‐pair electrons of the enethiolic sulphur atom and the ‘chelating’ methylene hydrogen atoms of cis‐alkyl groups.
• A new synthesis of cyclic allenic esters
  作者：Augustine Silveira、Michael Angelastro、Robert Israel、Frank Totino、Peter Williamsen

  DOI：10.1021/jo01305a034

  日期：1980.8