cyclohexa-1,3-dienyl acetate | 74502-18-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclohexa-1,3-dienyl acetate
• 英文别名: Cyclohexadienyl acetate；cyclohexa-1,3-dien-1-yl acetate
• CAS: 74502-18-4
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: DAQWLQVCDKFAPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclohexa-1,3-dienyl acetate 生成 (1-acetyloxy-4-tricyclo[6.2.2.02,7]dodeca-3,9-dienyl) acetate
  参考文献：
  名称：

  MLCOCH J.; STECKHAN E., TETRAHEDRON LETT., 28,(1987) N 10, 1081-1084

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-Diacetyloxycyclohex-3-ene-1-carboxylic acid 在 四(三苯基膦)钯 三乙胺 作用下， 生成 cyclohexa-1,3-dienyl acetate
  参考文献：
  名称：

  A new diene synthesis via organopalladium chemistry

  摘要：

  DOI：

  10.1021/ja00528a056

文献信息

• Acyloxybutadiene tricarbonyl iron complexes as enzyme-triggered CO-releasing molecules (ET-CORMs): a structure–activity relationship study
  作者：Steffen Romanski、Birgit Kraus、Miguel Guttentag、Waldemar Schlundt、Hannelore Rücker、Andreas Adler、Jörg-Martin Neudörfl、Roger Alberto、Sabine Amslinger、Hans-Günther Schmalz

  DOI：10.1039/c2dt30662j

  日期：——

  A series of η4-acyloxycyclohexadiene–Fe(CO)3 complexes was prepared and fully characterized by spectroscopic methods including single crystal X-ray diffraction. For this purpose a new synthetic access to differently acylated 1,3- and 1,5-dienol–Fe(CO)3 complexes was developed. The enzymatically triggered CO release from these compounds was monitored (detection of CO through GC and/or by means of a

  一系列η的4 -acyloxycyclohexadiene -铁（CO）3个，制备配合物和通过光谱方法，包括单晶X射线衍射完全表征。为此目的，一种新的合成方法可制得不同酰化的1,3-和1,5-二烯醇-Fe（CO）3复合体被开发出来。监测酶促触发的这些化合物释放的CO释放（通过GC和/或通过肌红蛋白测定法检测CO），并基于细胞对NO产生的抑制作用，通过细胞测定法评估化合物的抗炎作用诱导型一氧化氮合酶（iNOS）。结果表明，配合物的性质（酯酶触发的CO释放速率，iNOS抑制作用，细胞毒性）在很大程度上取决于π-配体的取代方式和酰氧基取代基的性质。
• ACYLOXY- AND PHOSPHORYLOXY-BUTADIENE-FE(CO)3 COMPLEXES AS ENZYME-TRIGGERED CO-RELEASING MOLECULES
  申请人：Schmalz Hans-Guenther

  公开号：US20120202774A1

  公开（公告）日：2012-08-09

  The present invention provides acyloxy- and phosphoryloxy-butadiene-Fe(CO) 3 complexes which can deliver carbon monoxide to a physiological target, wherein release of carbon monoxide can be enzymatically-triggered. The present invention also provides for methods of manufacturing the enzymatically-triggered carbon monoxide releasing molecules and methods for their use.

  本发明提供了能够将一氧化碳传递到生理靶点的酰氧基和磷酸酯氧基丁二烯-Fe(CO)3配合物，其中一氧化碳的释放可以通过酶触发。本发明还提供了制造酶触发一氧化碳释放分子的方法以及它们的使用方法。
• Acyloxybutadiene Iron Tricarbonyl Complexes as Enzyme-Triggered CO-Releasing Molecules (ET-CORMs)
  作者：Steffen Romanski、Birgit Kraus、Ulrich Schatzschneider、Jörg-Martin Neudörfl、Sabine Amslinger、Hans-Günther Schmalz

  DOI：10.1002/anie.201006598

  日期：2011.3.1

  Molecular hazardous materials transport: Enzyme‐triggered CO‐releasing molecules (ET‐CORMs) offer new options for the delivery of CO. The cleavage of dienylester iron tricarbonyl complexes by an esterase under mild oxidative conditions generates CO, which causes a strong inhibiting activity of the compounds to inducible nitric oxide synthase as shown in a cellular assay.

  分子危险物质的运输：酶触发的释放CO的分子（ET-CORMs）为释放CO提供了新的选择。在温和的氧化条件下，酯酶裂解二烯基三羰基铁复合物会产生CO，从而强烈抑制CO的释放。如细胞测定中所示，将化合物转化为诱导型一氧化氮合酶。
• Electrochemically induced [4+2]-cycloadditions - a mechanistic interpretation of the cation radical Diels-Alder reaction based on preparative results
  作者：Jiri Mlcoch、Eberhard Steckhan

  DOI：10.1016/s0040-4039(00)95916-1

  日期：1987.1

  For the first time it was possible to induce the cation-radical Diels-Alder reaction between electronrich dienes and electronrich dienophiles electrochemically, thus providing a clearer view upon the mechanism of this reaction type. In contrast to common explanations it could be demonstrated that this reaction most probably takes place via the cation radical of the diene. A role selectivity towards

  首次有可能电化学诱导富电子二烯和富电子二烯亲电子之间的阳离子自由基Diels-Alder反应，从而使这种反应类型的机理更清晰。与通常的解释相反，可以证明该反应最有可能通过二烯的阳离子自由基发生。可以排除对亲双烯体阳离子自由基的作用选择性。
• Mn-salen catalyzed asymmetric oxidation of enol derivatives
  作者：Tsutomu Fukuda、Tsutomu Katsuki

  DOI：10.1016/0040-4039(96)00858-1

  日期：1996.6

  Mn-salen complex 1 was found to catalyze highly enantioselective oxidation of enol ethers with iodosylbenzene as a terminal oxidant giving the corresponding hydroxy acetals, when the reaction was carried out in an alcoholic solvent. The reactions in the usual solvents such as dichloromethane and acetonitrile showed irregular and lower enantioselectivity, partly due to racemization of the resulting

  当反应在醇溶剂中进行时，发现Mn-salen配合物1以碘代苯作为末端氧化剂，催化烯醇醚的高度对映选择性氧化，得到相应的羟基缩醛。在常规溶剂（如二氯甲烷和乙腈）中的反应显示出不规则且较低的对映选择性，部分原因是所得α-羟基酮的外消旋化。

表征谱图