2-chloro-3-(ethoxymethoxy)cyclohexene | 474834-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-3-(ethoxymethoxy)cyclohexene
• 英文别名: 1-Chloro-6-(ethoxymethoxy)cyclohexene；1-chloro-6-(ethoxymethoxy)cyclohexene
• CAS: 474834-45-2
• 化学式: C₉H₁₅ClO₂
• 分子量: 190.67
• InChiKey: SPMDCVXGTCEAFR-UHFFFAOYSA-N

物化性质

• 沸点：
  231.5±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(ethoxymethoxy)cyclohexene 在 萘 、 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到3-(ethoxymethoxy)cyclohexene
  参考文献：
  名称：

  Six- and five-membered 3-alkoxy-2-lithiocycloalkenes: new stable non-anionic β-functionalised organolithium compounds

  摘要：

  Naphthalene-catalysed reductive lithiation of various functionalised chlorocycloalkenes 18 leads to the corresponding non-anionic beta-alkoxyfunctionalised organolithium reagents 14. Their reaction with different electrophiles, such as water, aldehydes, ketones and imines, gave the expected products 19 and 24. The diastereoselection in the reaction with aldehydes can be modified by the use of different additives. In the case of using 3-methoxy-2-chlorocyclopentene (18a) as starting material, and depending on reaction time, unexpected bicyclopentadiene derivatives 25 were isolated, together with the expected compounds 24. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00454-4
• 作为产物：
  描述：

  2-chlorocyclohex-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 2-chloro-3-(ethoxymethoxy)cyclohexene
  参考文献：
  名称：

  Six- and five-membered 3-alkoxy-2-lithiocycloalkenes: new stable non-anionic β-functionalised organolithium compounds

  摘要：

  Naphthalene-catalysed reductive lithiation of various functionalised chlorocycloalkenes 18 leads to the corresponding non-anionic beta-alkoxyfunctionalised organolithium reagents 14. Their reaction with different electrophiles, such as water, aldehydes, ketones and imines, gave the expected products 19 and 24. The diastereoselection in the reaction with aldehydes can be modified by the use of different additives. In the case of using 3-methoxy-2-chlorocyclopentene (18a) as starting material, and depending on reaction time, unexpected bicyclopentadiene derivatives 25 were isolated, together with the expected compounds 24. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00454-4

文献信息

• Six- and five-membered 3-alkoxy-2-lithiocycloalkenes: new stable non-anionic β-functionalised organolithium compounds
  作者：Miguel Yus、Diego J Ramón、Inmaculada Gómez

  DOI：10.1016/s0040-4020(02)00454-4

  日期：2002.6

  Naphthalene-catalysed reductive lithiation of various functionalised chlorocycloalkenes 18 leads to the corresponding non-anionic beta-alkoxyfunctionalised organolithium reagents 14. Their reaction with different electrophiles, such as water, aldehydes, ketones and imines, gave the expected products 19 and 24. The diastereoselection in the reaction with aldehydes can be modified by the use of different additives. In the case of using 3-methoxy-2-chlorocyclopentene (18a) as starting material, and depending on reaction time, unexpected bicyclopentadiene derivatives 25 were isolated, together with the expected compounds 24. (C) 2002 Elsevier Science Ltd. All rights reserved.