3-methyl-2-(trimethylsilyl)cyclopent-2-enone | 99698-53-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-methyl-2-(trimethylsilyl)cyclopent-2-enone
• 英文别名: 2-trimethylsilyl-3-methylcyclopentenone；2-Cyclopenten-1-one, 3-methyl-2-(trimethylsilyl)-；3-methyl-2-trimethylsilylcyclopent-2-en-1-one
• CAS: 99698-53-0
• 化学式: C₉H₁₆OSi
• 分子量: 168.311
• InChiKey: NIOPFQQBAOLRLE-UHFFFAOYSA-N

物化性质

• 沸点：
  200.6±39.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-2-(trimethylsilyl)cyclopent-2-enone 在 三氯化铝 、 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-iodo-3-methyl-2-cyclopentenone
  参考文献：
  名称：

  α碘α，β不饱和酮的α -甲硅烷基- α，β不饱和酮与ICl的或IClAlCl的反应的合成3

  摘要：

  处理α-甲硅烷基-α，β-不饱和烯酮，可以容易地制备为区域和立体定义的化合物，收率较高，为2当量。ICl或一个当量。ICl和AlCl 3各自以高收率提供相应的α-碘-α，β-不饱和烯酮。

  DOI：

  10.1016/s0040-4039(99)00635-8
• 作为产物：
  描述：

  2-溴-3-甲基-2-环戊烯-1-酮 在 sodium 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 生成 3-methyl-2-(trimethylsilyl)cyclopent-2-enone
  参考文献：
  名称：

  五元和六元环状α-酰基乙烯基阴离子合成子：α-三甲基甲硅烷基-α,β-不饱和环烯酮的合成及其通过碳硅键断裂转化为2-（羟基二甲基甲硅烷基）环烷-2-烯酮

  摘要：

  五元和六元 I±-trimethylsilyl-I±,I²-不饱和环烯酮是通过相应的 6-bromo-1,4-dioxaspiro4,ncycloalk-6-enes 与钠和氯三甲基硅烷的 Wurtz-Fittig 偶联反应制备的。用无水 AlCl3 处理后，这些化合物发生碳-硅键断裂，产生一类新的化合物：2-(羟基二甲基甲硅烷基)环烷-2-烯酮。© ARKAT-USA, Inc.

  DOI：

  10.3998/ark.5550190.0013.618

文献信息

• CuCl-catalyzed reaction of zirconacyclopentenes with oxalyl chloride: a new pathway for the preparation of cyclopentenones
  作者：Chao Chen、Yundong Liu、Chanjuan Xi

  DOI：10.1016/j.tetlet.2009.07.065

  日期：2009.9

  Zirconacyclopentenes, which are easily prepared from alkynes and EtMgBr (or ethylene) and Cp2ZrCl2, reacted with oxalyl chloride in the presence of catalytic amount of CuCl to give cyclopentenones in high yields. The reaction was performed conveniently in one pot from alkynes, EtMgBr, oxalyl chloride, and Cp2ZrCl2.

  容易从炔烃和EtMgBr（或乙烯）和Cp 2 ZrCl 2制备的锆碳环戊烯与草酰氯在催化量的CuCl存在下反应，以高收率得到环戊烯。该反应方便地在一锅中从炔烃，EtMgBr，草酰氯和Cp 2 ZrCl 2进行。
• Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO
  作者：Tamotsu Takahashi、Zhenfeng Xi、Yasushi Nishihara、Shouquan Huo、Kayoko Kasai、Koichiro Aoyagi、Victor Denisov、Ei-ichi Negishi

  DOI：10.1016/s0040-4020(97)00612-1

  日期：1997.7

  Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I-2 gave alpha,beta-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, alpha-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, alpha-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynytbenzene afforded alpha alpha'-bridged cyclopentenone compounds in good yields. (C) 1997 Elsevier Science Ltd.
• RAUTENSTRAUCH, V.;BURGER, U.;WIRTHNER, PH., CHIMIA, 1985, 39, N 7-8, 225-226
  作者：RAUTENSTRAUCH, V.、BURGER, U.、WIRTHNER, PH.

  DOI：——

  日期：——
• Five- and six–membered cyclic α-acylvinyl anionic synthons: synthesis of α-trimethylsilyl-α,β-unsaturated cycloalkenones and their conversion into 2-(hydroxydimethylsilyl)cycloalk-2-enones through carbon–silicon bond scission
  作者：Divya Jyothi、HariPrasad Suresh

  DOI：10.3998/ark.5550190.0013.618

  日期：——

  Five- and six-membered I±-trimethylsilyl-I±,I²-unsaturated cycloalkenones were prepared by the Wurtz-Fittig coupling reaction of the corresponding 6-bromo-1,4-dioxaspiro4,ncycloalk-6-enes with sodium and chlorotrimethylsilane. Upon treatment with anhydrous AlCl3, the compounds underwent carbon-silicon bond scission to yield a novel class of compounds: the 2-(hydroxydimethylsilyl)cycloalk-2-enones.

  五元和六元 I±-trimethylsilyl-I±,I²-不饱和环烯酮是通过相应的 6-bromo-1,4-dioxaspiro4,ncycloalk-6-enes 与钠和氯三甲基硅烷的 Wurtz-Fittig 偶联反应制备的。用无水 AlCl3 处理后，这些化合物发生碳-硅键断裂，产生一类新的化合物：2-(羟基二甲基甲硅烷基)环烷-2-烯酮。© ARKAT-USA, Inc.
• Synthesis of α-iodo-α,β-unsaturated ketones by the reaction of α-silyl-α,β-unsaturated ketones with ICl or IClAlCl3
  作者：Asaf Alimardanov、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(99)00635-8

  日期：1999.5

  Treatment of α-silyl-α,β-unsaturated enones, readily preparable as regio- and stereodefined compounds in high yields, with either 2 equiv. of ICl or one equiv. each of ICl and AlCl3 provides the corresponding α-iodo-α,β-unsaturated enones in high yields.

  处理α-甲硅烷基-α，β-不饱和烯酮，可以容易地制备为区域和立体定义的化合物，收率较高，为2当量。ICl或一个当量。ICl和AlCl 3各自以高收率提供相应的α-碘-α，β-不饱和烯酮。