1-(3-oxo-1-cyclohexenyl)-2-methylpropyl acetate | 128822-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-oxo-1-cyclohexenyl)-2-methylpropyl acetate
• 英文别名: [2-Methyl-1-(3-oxocyclohexen-1-yl)propyl] acetate
• CAS: 128822-78-6
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: PPUQKSSXIXHWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-bromo-2-methylpropyl acetate 、 3-Iodocyclohex-2-enone 在 lithium chloride 、 锌 作用下， 生成 1-(3-oxo-1-cyclohexenyl)-2-methylpropyl acetate
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010

文献信息

• A general preparation of highly functionalized zinc and copper organometallics at the .alpha.-position to an oxygen
  作者：Tso Sheng Chou、Paul Knochel

  DOI：10.1021/jo00303a007

  日期：1990.8
• CHOU, TSO-SHENG;KNOCHEL, PAUL, J. ORG. CHEM., 55,(1990) N6, C. 4791-4793
  作者：CHOU, TSO-SHENG、KNOCHEL, PAUL

  DOI：——

  日期：——