2-<2-(2-methyl-1,3-dioxolan-2-yl)ethyl>cyclohexanone | 61759-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<2-(2-methyl-1,3-dioxolan-2-yl)ethyl>cyclohexanone
• 英文别名: 2-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]cyclohexan-1-one
• CAS: 61759-46-4
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: UZISAHVPHOLMTK-UHFFFAOYSA-N

物化性质

• 沸点：
  308.1±17.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-(2-methyl-1,3-dioxolan-2-yl)ethyl>cyclohexanone 在 2,6-二甲基吡啶 、 正丁基锂 、 水 、 lithium perchlorate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 20.75h， 生成 α-1,7a-bis(dimethoxymethyl)-1-methyloctahydro-1H-indene
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: the use of bis enol ether substrates

  摘要：

  In an effort to develop electrochemical methods for directly initiating oxidative cyclization reactions, the anodic oxidation of bis enol ether substrates has been examined. The reactions were found to lead to the formation of five-, six-, and seven-membered-ring 1,4-dicarbonyl equivalents. The reactions were not found to be useful for generating larger ring sizes. Both alkyl and silyl enol ether substrates were found to be compatible with the conditions required for carbon-carbon bond formation. Cyclic voltammetry studies indicated that the cyclizations were fast and that the reactions happened at or near the electrode surface. Finally, the cyclization reactions were shown to be compatible with the formation of quaternary carbons, even when carbon-carbon bond formation involved the generation of two vicinal quaternary carbons.

  DOI：

  10.1021/ja00029a036
• 作为产物：
  描述：

  2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]cyclohexan-1-ol 以97%的产率得到
  参考文献：
  名称：

  PONARAS A. A., TETRAHEDRON LETT. , 1976, NO 36, 3105-3108

  摘要：

  DOI：

文献信息

• Perhydrolysis in Ethereal H₂O₂ Mediated by MoO₂(acac)₂: Distinct Chemoselectivity between Ketones, Ketals, and Epoxides
  作者：Xiaosheng An、Qinghong Zha、Yikang Wu

  DOI：10.1021/acs.orglett.9b00425

  日期：2019.3.1

  Ketones, ketals, and epoxides were converted into corresponding hydroperoxides in high yields by reaction with ethereal H2O2 in the presence of a catalytic amount of MoO2(acac)2 with distinct (to date unattainable) chemoselectivity.

  在催化量的MoO 2（acac）2具有催化选择性（迄今为止无法实现）的条件下，通过与醚H 2 O 2反应，高产率地将酮，缩酮和环氧化物转化为相应的氢过氧化物。
• Simple Analogues of Qinghaosu (Artemisinin)
  作者：Yun Li、Hong‐Dong Hao、Sergio Wittlin、Yikang Wu

  DOI：10.1002/asia.201200166

  日期：2012.8

  A series of 1,2,4‐trioxanes were synthesized in which the key peroxy bonds were installed through a molybdenum‐catalyzed perhydrolysis of the epoxy rings. A core structure was identified that may serve as a promising lead structure for further investigations because of its high antimalarial activity (comparable to that of artesunate and chloroquine), apparent potential for scale‐up and derivatization

  合成了一系列 1,2,4-三恶烷，其中关键的过氧键是通过钼催化的环氧环过水解安装的。确定了一个核心结构，由于其高抗疟活性（与青蒿琥酯和氯喹相当）、放大和衍生化的明显潜力以及使用紫外光易于监测/追踪，因此可以作为有希望的进一步研究的先导结构.
• Synthesis of (+)-Panamonon B, 7-<i>epi</i>-Panamonon B, and Their (<i>Z</i>)-Isomers
  作者：Xiaosheng An、Yikang Wu

  DOI：10.1021/acs.joc.1c01344

  日期：2021.9.3

  B was synthesized with the key quaternary center (of a predefined absolute configuration) installed using Stoltz asymmetric allylation. The C-5 ketone functionality and the cross-conjugated enone moiety in the side chain were introduced via a photosensitized [2+4] cycloaddition of singlet oxygen to diene silyl enol ether and an aldol condensation under the conditions of Sugiura, respectively. The 1H

  (+)-Panamonon B 是使用 Stoltz 不对称烯丙基化安装的关键四元中心（具有预定义的绝对构型）合成的。侧链中的 C-5 酮官能团和交叉共轭的烯酮部分分别通过单线态氧与二烯甲硅烷基烯醇醚的光敏 [2+4] 环加成和在 Sugiura 条件下的羟醛缩合引入。合成样品和天然样品的1 H 和13 C NMR 彼此完全一致。然而，因为两个样品的旋光度符号相反，所以它们一定是彼此的对映体。该合成还提供了宝贵的机会来观察意想不到但相当有趣的现象，例如环己烷环轴向位置的庞大取代基和（E )-和 ( Z )-异构体尽管具有相同的立体中心，但旋光度符号相反。由于四元中心的存在和与六元环稠合的五元内酯的形成，环己烷环轴向位置上罕见的大取代基被合理化，而迄今为止未被注意到的影响旋光中的 C=C 几何结构与从文献中检索到的几对类似化合物中封装的信息一致。
• Simplified analogues of qinghaosu (artemisinin)
  作者：Qi Zhang、Yikang Wu

  DOI：10.1016/j.tet.2007.08.018

  日期：2007.10

  Three new simplified analogues of qinghaosu have been designed and synthesized through simple routes without recourse to the commonly employed photosensitized oxidation. The peroxy bonds in the target molecules were taken from UHP with the first peroxy–carbon bond formed through a hemiketal exchange reaction and the second by either an intramolecular Michael addition or a Hg(II)-mediated ring-closure

  通过简单的途径设计并合成了三种新的青蒿素的简化类似物，而无需依靠常用的光敏氧化。目标分子中的过氧键取自UHP，第一个过氧-碳键通过半交换反应形成，第二个通过分子内迈克尔加成反应或通过Hg（II）介导的闭环反应形成。所有这三种过氧化物均具有一个与全碳六元环稠合的七元过氧环，这是生成以碳为中心的取代乙基基团所需的结构基序。
• A Broadly Applicable Mild Method for the Synthesis of <i>gem</i>-Diperoxides from Corresponding Ketones or 1,3-Dioxolanes
  作者：Yun Li、Hong-Dong Hao、Qi Zhang、Yikang Wu

  DOI：10.1021/ol900262t

  日期：2009.4.2

  Ketones or ketals were readily converted into the corresponding gem-dihydroperoxides in high yields by treatment with ethereal H2O2 at ambient temperature in the presence of 2-5 mol % of phosphomolybdic acid.