2-(2-cyanoethyl)-1-(methoxymethylene)cyclohexane | 209809-61-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-cyanoethyl)-1-(methoxymethylene)cyclohexane
• 英文别名: 3-[2-(Methoxymethylidene)cyclohexyl]propanenitrile
• CAS: 209809-61-0
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: MELWOMMUNXAPPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-cyanoethyl)-1-(methoxymethylene)cyclohexane 在 亚磷酸三苯酯 、 叔丁基锂 、 臭氧 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 4.33h， 生成 (1R,6S,9R,12S)-12-Methoxy-9-(3-methylsulfanyl-phenyl)-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridecane
  参考文献：
  名称：

  Antimalarial sulfide, sulfone, and sulfonamide trioxanes

  摘要：

  A series of trioxanes featuring sulfide, sulfone. and sulfonamide snbstituents in diverse positions has been prepared. Structure-activity relationship (SAR) generalizations highlight two major factors controlling the antimalarial potency of these new chemical entities: (1) the proximity of the sulfur-containing substituent to the crucial peroxide bond and (2) the oxidation stale of the sulfur-containing substituent. Generally, sulfones are more antimalarially potent than the corresponding sulfides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00079-1
• 作为产物：
  描述：

  2-氧-1-环己烷丙腈 、 甲氧基甲基三苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.0h， 以81%的产率得到2-(2-cyanoethyl)-1-(methoxymethylene)cyclohexane
  参考文献：
  名称：

  Antimalarial Simplified 3-Aryltrioxanes:  Synthesis and Preclinical Efficacy/Toxicity Testing in Rodents

  摘要：

  A streamlined five-step chemical synthesis of rationally designed, simplified 3-aryltrioxane 8a is described. A noteworthy feature of this synthetic scheme is use of air rather than expensive molecular oxygen as the source of the pharmacologically critical peroxide unit in trioxane 8a. This simplified acetal trioxane carboxylic acid 8a is thermally stable, and it is hydrolytically stable in water even at 40 degreesC and pH 7.4 for at least 7 days. Preclinical evaluation of this water-soluble synthetic trioxane 8a in rodents shows it to have at least as good a therapeutic index (efficacy/toxicity) as that of water-soluble semisynthetic trioxane artelinic acid (5).

  DOI：

  10.1021/jm0102396