diethyl 2-(ethoxycarbonyl)cyclohexenyl phosphate | 100544-05-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: diethyl 2-(ethoxycarbonyl)cyclohexenyl phosphate
• 英文别名: 2-(diethoxy-phosphoryloxy)-cyclohex-1-enecarboxylic acid ethyl ester；<2-Aethoxycarbonyl-cyclohexen-(1)-yl>-diaethyl-phosphat；Phosphorsaeure-diaethyl-(2-aethoxycarbonyl-cyclohex-1-enyl)-ester；(2-Aethoxycarbonyl-cyclohexen-(1)-yl)-diaethyl-phosphat；Ethyl 2-diethoxyphosphoryloxycyclohexene-1-carboxylate
• CAS: 100544-05-6
• 化学式: C₁₃H₂₃O₆P
• 分子量: 306.296
• InChiKey: JIKDEWGKZCTMIB-UHFFFAOYSA-N

物化性质

• 沸点：
  135-140 °C(Press: 0.15 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-(ethoxycarbonyl)cyclohexenyl phosphate 在 吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 copper(l) iodide 、 草酰氯 、 碳酸氢钠 、 magnesium 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 52.0h， 生成 2-<<(4-fluorophenyl)telluro>methyl>-1,2,3,4,5,6,7,8-octahydronaphthalen-1-one
  参考文献：
  名称：

  Photoinduced Free Radical Chemistry of the Acyl Tellurides: Generation, Inter- and Intramolecular Trapping, and ESR Spectroscopic Identification of Acyl Radicals

  摘要：

  Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-alpha-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are alpha-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords alpha-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the alpha-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields alpha-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.

  DOI：

  10.1021/ja00099a011
• 作为产物：
  描述：

  氯磷酸二乙酯 、 2-环己酮甲酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到diethyl 2-(ethoxycarbonyl)cyclohexenyl phosphate
  参考文献：
  名称：

  一些 2-OXASPIRO[3.5]NONA-1-ONE 的高效合成作为茴香素模型

  摘要：

  作为合成茴香素的模型研究，分别从环己烷羧酸甲酯和 2-乙氧羰基环己酮合成了 2-氧杂螺[3.5]壬烷和 5-羟基-5-甲基-2-氧杂螺[3.5]壬烷，并提交了这些氧杂环丁烷四氧化钌氧化得到相应的β-内酯。

  DOI：

  10.1246/cl.1985.1785

文献信息

• (2-hydroxy)ethyl-thioureas useful as modulators of alpha2B adrenergic receptors
  申请人：ALLERGAN SALES, INC.

  公开号：US20020161051A1

  公开（公告）日：2002-10-31

  Compounds of formula (i) and of formula (ii) 1 wherein the symbols have the meaning disclosed in the specification, specifically or selectively modulate &agr; 2B and/or &agr; 2C adrenergic receptors in preference over &agr; 2A adrenergic receptors, and as such are useful for alleviating chronic pain and allodynia and have no or only minimal cardivascular and/or sedatory activity.

  式（i）和式（ii）的化合物 其中符号的含义在说明书中披露，特别或选择性地调节&agr; 2B 和/或&agr; 2C 肾上腺素受体，优先于&agr; 2A 肾上腺素受体，因此对缓解慢性疼痛和触痛有用，并且几乎没有或只有极小的心血管和/或镇静活性。
• (2-HYDROXY)ETHYL-THIOUREAS USEFUL AS MODULATORS OF ALPHA2B ADRENERGIC RECEPTORS
  申请人：Allergan, Inc.

  公开号：EP1381593A2

  公开（公告）日：2004-01-21
• US6534542B2
  申请人：——

  公开号：US6534542B2

  公开（公告）日：2003-03-18
• [EN] (2-HYDROXY)ETHYL-THIOUREAS USEFUL AS MODULATORS OF ALPHA2B ADRENERGIC RECEPTORS<br/>[FR] (2-HYDROXY)ETHYLTHIOUREAS UTILES EN TANT QUE MODULATEURS DES RECEPTEURS ADRENERGIQUES ALPHA2B
  申请人：ALLERGAN INC

  公开号：WO2002068384A2

  公开（公告）日：2002-09-06

  Compounds of formula (i) and of formula (ii), wherein the symbols have the meaning disclosed in the claims, specifically or selectively modulate α2A adrenergic receptors and as such are useful for alleviating chronic pain and allodynia and have no or only minimal cardiovascular and/or sedatory activity. The invention also relates to a method of activating α2B or α2C adrenergic receptors in a mammal by administering a compound that has α2Bor α2C adrenergic receptor activity and has no significant α2A agonist activity.
• Photoinduced Free Radical Chemistry of the Acyl Tellurides: Generation, Inter- and Intramolecular Trapping, and ESR Spectroscopic Identification of Acyl Radicals
  作者：David Crich、Chen Chen、Jae-Taeg Hwang、Hongwei Yuan、Aristotle Papadatos、Robert I. Walter

  DOI：10.1021/ja00099a011

  日期：1994.10

  Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-alpha-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are alpha-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords alpha-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the alpha-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields alpha-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.