2-methoxy-2-(4-chlorophenyl)cyclohexanone | 190256-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-2-(4-chlorophenyl)cyclohexanone
• 英文别名: 2-(4-Chlorophenyl)-2-methoxycyclohexan-1-one
• CAS: 190256-59-8
• 化学式: C₁₃H₁₅ClO₂
• 分子量: 238.714
• InChiKey: RWPBRPIFXYFSHU-UHFFFAOYSA-N

物化性质

• 沸点：
  341.5±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

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：
  0.46
• 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：

  di-tert-butyl (E)-azodicarboxylate 、 2-methoxy-2-(4-chlorophenyl)cyclohexanone 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95%的产率得到tert-butyl N-[1-(4-chlorophenyl)-2-oxocyclohexyl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]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：

  1-(4-氯苯基)-1-环己烯 在 jones reagent 、 硫酸 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 3.0h， 生成 2-methoxy-2-(4-chlorophenyl)cyclohexanone
  参考文献：
  名称：

  由SmI 2介导的还原作用衍生自α-杂取代的酮和内酯的烯醇sa的对映选择性质子化

  摘要：

  SmI 2介导的α-烷基或α-芳基酮的α-杂取代基和内酯的还原裂解产生相应的“热力学sa烯醇盐”。用C 2对称手性二醇对烯醇盐进行对映选择性质子化，可得到中等至高对映选择性的相应酮和内酯。

  DOI：

  10.1016/s0040-4020(99)00143-x

文献信息

• SmI2-mediated reductive enolization of α-hetero-substituted ketones and enantioselective protonation
  作者：Yutaka Nakamura、Seiji Takeuchi、Yoshiaki Ohgo、Makoto Yamaoka、Akihiro Yoshida、Koichi Mikami

  DOI：10.1016/s0040-4039(97)00435-8

  日期：1997.4

  High enantioselectivity (up to 94% ee) has been achieved in the protonation of samarium enolates which were generated by SmI2-mediated reduction of 2-aryl-2-methoxycyclohexanones using a C2-symmetric chiral diol as a proton source.

  在of烯醇盐的质子化中已经实现了高对映选择性（高达94％ee），sa烯醇盐是通过SmI 2介导的还原反应（使用C 2对称手性二醇作为质子源生成的2-芳基-2-甲氧基环己酮）而生成的。
• 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.
• Enantioselective protonation of samarium enolates derived from α-heterosubstituted ketones and lactone by SmI2-mediated reduction
  作者：Yutaka Nakamura、Seiji Takeuchi、Yoshiaki Ohgo、Makoto Yamaoka、Akihiro Yoshida、Koichi Mikami

  DOI：10.1016/s0040-4020(99)00143-x

  日期：1999.4

  SmI2-mediated reductive cleavage of α-hetero substituents of α-alkyl or α-aryl ketones and lactone gave the corresponding “thermodynamic samarium enolates”. Enantioselective protonation of the samarium enolates with C2-symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.

  SmI 2介导的α-烷基或α-芳基酮的α-杂取代基和内酯的还原裂解产生相应的“热力学sa烯醇盐”。用C 2对称手性二醇对烯醇盐进行对映选择性质子化，可得到中等至高对映选择性的相应酮和内酯。
• 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.