Trimethyl-[1-(trifluoromethyl)cyclohex-2-en-1-yl]oxysilane | 247912-53-4

• 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: Trimethyl-[1-(trifluoromethyl)cyclohex-2-en-1-yl]oxysilane
• CAS: 247912-53-4
• 化学式: C₁₀H₁₇F₃OSi
• 分子量: 238.325
• InChiKey: CXJAMXXSDJGFBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Trimethyl-[1-(trifluoromethyl)cyclohex-2-en-1-yl]oxysilane 在 硫酸 、 四丁基氟化铵 、 水 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 3-trifluoromethyl-2-cyclohexene-1-one
  参考文献：
  名称：

  三氟甲基化叔烯丙基醇与氯铬酸吡啶鎓的氧化重排制备3-三氟甲基-2-环烯酮

  摘要：

  由几种共轭烯酮的三氟甲基化制得的三氟甲基化叔烯丙醇，在少量浓H 2 SO 4的存在下，与氯铬酸吡啶鎓发生氧化重排反应，生成3-三氟甲基-2-环烯酮。

  DOI：

  10.1016/s0022-1139(99)00159-1
• 作为产物：
  描述：

  2-环己烯-1-酮 、 (三氟甲基)三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 Trimethyl-[1-(trifluoromethyl)cyclohex-2-en-1-yl]oxysilane
  参考文献：
  名称：

  One Flask Preparation of Trifluoromethylated Amides from Ketones and Trifluoromethyltrimethylsilane via Ritter Reaction with Nitriles

  摘要：

  三氟甲基酰胺可通过简单的单瓶反应制备，即通过相应三氟甲基硅醚的Ritter反应得到。这些硅醚本身很容易从起始的酮和三氟甲基三甲基硅烷制得。产率良好至一般。

  DOI：

  10.1055/s-1997-989

文献信息

• One Flask Preparation of Trifluoromethylated Amides from Ketones and Trifluoromethyltrimethylsilane <i>via</i> Ritter Reaction with Nitriles
  作者：Emily Tongco、G. Surya Prakash、George Olah

  DOI：10.1055/s-1997-989

  日期：1997.10

  Trifluoromethylated amides are prepared in a simple one-flask reaction via the Ritter reaction of the corresponding trifluoromethylated silyl ethers, which themselves are readily obtained from the starting ketones and trifluoromethyltrimethylsilane. The yields are good to average.

  三氟甲基酰胺可通过简单的单瓶反应制备，即通过相应三氟甲基硅醚的Ritter反应得到。这些硅醚本身很容易从起始的酮和三氟甲基三甲基硅烷制得。产率良好至一般。
• CsF-Catalyzed Nucleophilic Trifluoromethylation of <i>trans</i>-Enones with Trimethyl(trifluoromethyl)silane:  A Facile Synthesis of <i>trans</i>-α-Trifluoromethyl Allylic Alcohols
  作者：Rajendra P. Singh、Robert L. Kirchmeier、Jean'ne M. Shreeve

  DOI：10.1021/ol990844r

  日期：1999.10.1

  [GRAPHICS]Reactions of trans-enones, R-C=C-COR' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (la-e), with TMS-CF3 in the presence of catalytic amounts of cesium fluoride (CsF) in ethylene glycol dimethyl ether led to the formation of the corresponding trans-alpha-trifluoromethyl silyl ethers, R-C=C-C(OSiMe3)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (2a-e), in essentially quantitative yield. On hydrolysis with aqueous HCl, the corresponding trans-alpha-trifluaromethyl allylic alcohols, R-C=C-C(OH)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Et, CF3) (3a-e), were formed in >90% isolated yield. Under similar reaction conditions, 2-cyclohexen-1-one (1f) also gave trifluoromethyl allylic alcohols (3f) in 92% yield. The intermediates (2a-f) and products (3a-f) are liquids and were characterized by IR, H-1, (19)f and C-13 NMR, MS, and high-resolution mass spectroscopy (HRMS).
• Preparation of 3-trifluoromethyl-2-cycloalkenones by the oxidative rearrangement of trifluoromethylated tertiary allylic alcohols with pyridinium chlorochromate
  作者：G.K.Surya Prakash、Emily C. Tongco、Thomas Mathew、Yashwant D. Vankar、George A. Olah

  DOI：10.1016/s0022-1139(99)00159-1

  日期：2000.2

  Trifluoromethylated tertiary allylic alcohols, obtained from trifluoromethylation of several conjugated enones, undergo oxidative rearrangements to 3-trifluoromethyl-2-cycloalkenones with pyridinium chlorochromate in the presence of a small amount of concentrated H2SO4.

  由几种共轭烯酮的三氟甲基化制得的三氟甲基化叔烯丙醇，在少量浓H 2 SO 4的存在下，与氯铬酸吡啶鎓发生氧化重排反应，生成3-三氟甲基-2-环烯酮。