2-甲氧基-2-苯基环庚烷-1-酮 | 6976-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基-2-苯基环庚烷-1-酮
• 英文名称: 2-methoxy-2-phenyl-cycloheptanone
• 英文别名: 2-Methoxy-2-phenyl-cycloheptanon；2-Methoxy-2-phenylcycloheptanone；2-methoxy-2-phenylcycloheptan-1-one
• CAS: 6976-76-7
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: UZQKWGBNLQHSTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲氧基-2-苯基环庚烷-1-酮 、 di-tert-butyl (E)-azodicarboxylate 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylamino]-N-(2-oxo-1-phenylcycloheptyl)carbamate
  参考文献：
  名称：

  Samarium diiodide-promoted electrophilic amination of ketone enolates: efficient synthesis of quaternary carbon-containing α-aminated ketones

  摘要：

  An efficient and practical electrophilic amination method that allows the preparation of useful quaternary carbon-containing alpha-aminoketones was developed. The reaction proceeds regiospecifically via a samarium enolate intermediate at room temperature in the presence of mild reducing agent SmI2. Unlike the most reported lithium enolate cases, this new amination method does not require the use of strong base such as BuLi or LDA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.123
• 作为产物：
  描述：

  2-甲氧基-2-苯基-1-氧杂-螺[2.5]辛烷 在 二丁醚 、 magnesium bromide 作用下， 生成 2-甲氧基-2-苯基环庚烷-1-酮
  参考文献：
  名称：

  Epoxyethers. IX. Acid-catalyzed Rearrangements¹

  摘要：

  DOI：

  10.1021/ja01646a039

文献信息

• Rapid assembly of anti-1,3-diol units with 2-quaternary carbon stereocenter via samarium diiodide-promoted tandem Aldol/Evans-Tishchenko reaction
  作者：Xing-Wen Sun、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1016/j.tetlet.2009.02.104

  日期：2009.7

  An efficient and practical method for highly diastereoselective synthesis of 2-quaternary anti-1,3-diol units With three adjacent stereogenic carbon centers has been developed. The reactions proceed regiospecifically at room temperature via samarium diiodide-promoted tandem Aldol condensation and Evans-Tishchenko reduction. The relative stereochemistry of the resulting 1,3-diol monoesters is identified by X-ray crystallography. (C) 2009 Elsevier Ltd. All rights reserved.
• Epoxyethers. IX. Acid-catalyzed Rearrangements¹
  作者：Calvin L. Stevens、Stanley J. Dykstra

  DOI：10.1021/ja01646a039

  日期：1954.9
• Samarium diiodide-promoted electrophilic amination of ketone enolates: efficient synthesis of quaternary carbon-containing α-aminated ketones
  作者：Xing-Wen Sun、Wei Wang、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1016/j.tetlet.2008.07.123

  日期：2008.9

  An efficient and practical electrophilic amination method that allows the preparation of useful quaternary carbon-containing alpha-aminoketones was developed. The reaction proceeds regiospecifically via a samarium enolate intermediate at room temperature in the presence of mild reducing agent SmI2. Unlike the most reported lithium enolate cases, this new amination method does not require the use of strong base such as BuLi or LDA. (C) 2008 Elsevier Ltd. All rights reserved.