3-(1-hydroxy-1-methylethyl)-2-cyclohexenone | 72842-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-hydroxy-1-methylethyl)-2-cyclohexenone
• 英文别名: 1-(α-Hydroxyisopropyl)-Δ¹-cyclohexan-3-on；3-(2-Hydroxypropan-2-yl)cyclohex-2-en-1-one；3-(2-hydroxypropan-2-yl)cyclohex-2-en-1-one
• CAS: 72842-23-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: AAFYRRDFZAHZAR-UHFFFAOYSA-N

物化性质

• 沸点：
  278.3±19.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-chloro-1,4-dioxaspiro[4,5]dec-6-ene 在 4,4'-二叔丁基苯并 、 草酸 、 silica gel 、 lithium 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.17h， 生成 3-(1-hydroxy-1-methylethyl)-2-cyclohexenone
  参考文献：
  名称：

  Ketalised α- and β-lithiated α,β-unsaturated ketones: New masked acylvinyl anion equivalents

  摘要：

  The reaction of chloroketals 1, 5 and 10 with an excess of lithium powder and a catalytic amount of DTBB (4-5%) in THF at -78 or -90 degrees C leads to the corresponding functionalised organolithium compounds 2, 6 and 11, respectively, resulting from a chlorine/lithium exchange; treatment of these intermediates with different electrophiles [H2O, D2O, Me(3)SiCl, Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(4)CO, (CH2)(5)CO, PhCOMe] affords, after hydrolysis with water, the corresponding products 3, 7 and 12, respectively. Careful acidic hydrolysis of these ketalised products with a 10% aqueous solution of oxalic acid leads to the expected ketones 4, 9 and 13, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00187-7

文献信息

• Simple Analogs of the Toxin Callicarpone
  作者：James D. McChesney、Pokar M. Kabra、Philip Fraher

  DOI：10.1002/jps.2600680915

  日期：1979.9

  Callicarpone, a component 10 times as toxic to fish as rotenone, has been isolated from the leaves of Callicarpa candicans. It is reasonable to assume that callicarpone will act as an insecticidal agent as does rotenone. Therefore, the structure-activity relationship of callicarpone was examined by synthesizing a series of compounds having certain of its structural features. Those compounds were tested

  卡利卡彭（Callicarpone）对鱼的毒性是鱼藤酮的10倍，已从加拿大卡利卡帕州的叶子中分离出来。可以合理地假设，卡普卡酮将像鱼藤酮一样起杀虫剂的作用。因此，通过合成一系列具有某些结构特征的化合物来检验卡皮卡普的构效关系。测试了这些化合物的杀虫和抗菌活性。合成类似物的研究阐明了卡皮卡酮的官能团化学性质，因此可以进行合成。氧化哌啶酮显示鱼藤酮对大型蚤（Daphnia magna）的活性约为其的1/100。1-（α-羟基异丙基）-3-氧代环己烯氧化物对肌分枝杆菌有活性，而2,3,4,6,7,8-六氢萘-1，