methyl(1-methyl-1-phenylethyl)ketene | 167212-08-0

• 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: methyl(1-methyl-1-phenylethyl)ketene
• 英文别名: Methyl (1-methyl-1-phenylethyl)ketene
• CAS: 167212-08-0
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: ZWQZJPMPHHZKAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 methyl(1-methyl-1-phenylethyl)ketene 在 palladium on activated charcoal 六甲基磷酰三胺 、 samarium diiodide 、 α,α'-di<(S)-2-hydroxy-2-phenylethyl>-o-xylenedioxide 、 氢气 作用下， 生成 (R)-2,3-dimethyl-2-phenyl-4-heptanone
  参考文献：
  名称：

  Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol

  摘要：

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.

  DOI：

  10.1016/0957-4166(94)80086-3
• 作为产物：
  描述：

  2,3-二甲基-3-苯基丁酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 35.0h， 生成 methyl(1-methyl-1-phenylethyl)ketene
  参考文献：
  名称：

  Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol

  摘要：

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.

  DOI：

  10.1016/0957-4166(94)80086-3

文献信息

• Catalytic enantioselective protonation of samarium enolates by a C2-symmetric chiral diol
  作者：Yutaka Nakamura、Seiji Takeuchi、Akiko Ohira、Yoshiaki Ohgo

  DOI：10.1016/0040-4039(96)00434-0

  日期：1996.4

  Relatively high enantioselectivity (up to 93% ee) has been achieved in the catalytic protonation of samarium enolates by the use of a C2-symmetric homochiral diol as the catalyst and trityl alcohol as an achiral proton source for regeneration of the catalyst.

  通过使用C 2对称均手性二醇作为催化剂和三苯甲基醇作为非手性质子源来再生sa烯酸pro ，在催化质子化烯醇盐中实现了相对较高的对映选择性（高达93％ee）。
• 10.1016/s0040-4039(98)01900-5
  作者：Takeuchi, Seiji、Nakamura, Yutaka、Ohgo, Yoshiaki、Curran, Dennis P.

  DOI：10.1016/s0040-4039(98)01900-5

  日期：——

  Enantioselectivities near maximum values were obtained in the catalytic reaction by a ropid addition of a fluorous achiral alcohol (Rfh3COH) to the reaction mixture: for DHPEX in Rfh3COH/THF solid-liquid biphase system and for a fluorous chiral alcohol in THF/FC-72 liquid-liquid biphase system.

  由ropid添加氟的非手性醇（RFH的催化反应获得接近最大值的对映选择性3为DHPEX在RFH：COH）加入到反应混合物3 COH/ THF固液两相体系和用于氟THF / FC-72液-液双相系统中的手性醇。
• Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol
  作者：Seiji Takeuchi、Akiko Ohira、Norikazu Miyoshi、Hajime Mashio、Yoshiaki Ohgo

  DOI：10.1016/0957-4166(94)80086-3

  日期：1994.9

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.