(3,3-(dichloro)propenoyl)trimethylsilane | 145571-76-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3,3-(dichloro)propenoyl)trimethylsilane
• 英文别名: 3,3-Dichloro-1-trimethylsilylprop-2-en-1-one
• CAS: 145571-76-2
• 化学式: C₆H₁₀Cl₂OSi
• 分子量: 197.136
• InChiKey: LDRBKKLCLDTEHD-UHFFFAOYSA-N

物化性质

• 沸点：
  167.3±40.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3,3-(dichloro)propenoyl)trimethylsilane 在 三甲基氯硅烷 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到E-3-chloro-1-(trimethylsilyl)-2-propenone
  参考文献：
  名称：

  A conjugate addition-elimination route to alkenoyltrimethylsilanes

  摘要：

  Monosubstitution of 3,3-dichloro-1-(trimethylsilyl)2-propenone (1) with organocuprates stereoselectively affords E-3-alkyl- and Z-3-phenyl-3-chloro-1-(trimethylsilyl)-2-propenones. Further substitution proceeds stereoselectively as a function of extant and incoming substituents. 1 was also reduced to E-3-chloro-1-(trimethylsilyl)-2-propenone and the latter converted to E-3-alkyl- and E-3-phenyl-1-(trimethylsilyl)-2-propenones.

  DOI：

  10.1016/0040-4020(95)00561-l
• 作为产物：
  描述：

  三氯溴甲烷 、 (1-乙氧基乙烯基)-三甲基硅烷 在 吡啶 、 甲醇 、 水 作用下， 生成 (3,3-(dichloro)propenoyl)trimethylsilane
  参考文献：
  名称：

  A conjugate addition-elimination route to alkenoyltrimethylsilanes

  摘要：

  Monosubstitution of 3,3-dichloro-1-(trimethylsilyl)2-propenone (1) with organocuprates stereoselectively affords E-3-alkyl- and Z-3-phenyl-3-chloro-1-(trimethylsilyl)-2-propenones. Further substitution proceeds stereoselectively as a function of extant and incoming substituents. 1 was also reduced to E-3-chloro-1-(trimethylsilyl)-2-propenone and the latter converted to E-3-alkyl- and E-3-phenyl-1-(trimethylsilyl)-2-propenones.

  DOI：

  10.1016/0040-4020(95)00561-l

文献信息

• Synthesis of 4-Hydroxy-2-cyclopentenone Derivatives by [3 + 2] Annulation of β-Heteroatom-Substituted Acryloylsilanes and Lithium Enolate of Methyl Ketones
  作者：Kei Takeda、Yasuhiro Ohtani、Emi Ando、Ken-ichi Fujimoto、Eiichi Yoshii、Toru Koizumi

  DOI：10.1246/cl.1998.1157

  日期：1998.11

  The [3 + 2] annulation using β-[2-(pyridyl)thio] and β,β-dichloro derivatives of acryloylsilane and the lithium enolate of methyl ketones successfully proceeded to afford 4-alkyl-4-hydroxy-3-(2-pyridylthio)cyclopentanone and 4-alkyl-3-chloro-4-hydroxy-2-cyclopentenone, respectively.

  丙烯酰硅烷的β-[2-(吡啶基)硫代]和β,β-二氯衍生物与甲基酮的烯醇锂成功地进行[3+2]环化，得到4-烷基-4-羟基-3-(2 -吡啶硫基）环戊酮和 4-烷基-3-氯-4-羟基-2-环戊烯酮，分别。
• The preparation of 3-chloroalkenoyltrimethylsilanes
  作者：Robert F. Cunico、Cui-ping Zhang

  DOI：10.1016/s0040-4039(00)61767-7

  日期：1992.11

  3,3-Dichloropropenoyltrimethylsilane undergoes monosubstitution with organocuprates RCu(CN)Li to afford E-3-chloroalkenoyltrimethylsilanes.
• Preparation of Allenoyltrmethylsilanes
  作者：Robert F. Cunico、Cui-ping Zhang

  DOI：10.1080/00397919508011383

  日期：1995.2

  Dehydrochlorination of 3-chloro-2- or -3-alkenoyltrimethylsilanes with DBU affords the parent 2,3-butadienoyltrimethylsilane, as well as 4-monoalkyl- and 4,4-dialkyl homologues.
• A conjugate addition-elimination route to alkenoyltrimethylsilanes
  作者：Robert F. Cunico、Cui-ping Zhang

  DOI：10.1016/0040-4020(95)00561-l

  日期：1995.1

  Monosubstitution of 3,3-dichloro-1-(trimethylsilyl)2-propenone (1) with organocuprates stereoselectively affords E-3-alkyl- and Z-3-phenyl-3-chloro-1-(trimethylsilyl)-2-propenones. Further substitution proceeds stereoselectively as a function of extant and incoming substituents. 1 was also reduced to E-3-chloro-1-(trimethylsilyl)-2-propenone and the latter converted to E-3-alkyl- and E-3-phenyl-1-(trimethylsilyl)-2-propenones.