3,3,3-trifluoro-2-methyl-1-phenyl-2-((trimethylsilyl)oxy)propan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,3-trifluoro-2-methyl-1-phenyl-2-((trimethylsilyl)oxy)propan-1-one
• 英文别名: 3,3,3-Trifluoro-2-methyl-1-phenyl-2-trimethylsilyloxypropan-1-one；3,3,3-trifluoro-2-methyl-1-phenyl-2-trimethylsilyloxypropan-1-one
• 化学式: C₁₃H₁₇F₃O₂Si
• 分子量: 290.357
• InChiKey: HDQSQDSCEPAZCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• 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：
  5

反应信息

• 作为产物：
  描述：

  1,1,1-三氟丙酮 、 三甲基硅基苯甲酮 以 正己烷 为溶剂， 反应 2.0h， 以99%的产率得到3,3,3-trifluoro-2-methyl-1-phenyl-2-((trimethylsilyl)oxy)propan-1-one
  参考文献：
  名称：

  氟化酮作为诱捕剂用于可见光诱导的单线态亲核性卡宾

  摘要：

  仅包含一个杂原子供体的单重亲核碳烯（SNC）在化学合成中仍未得到充分利用。我们最近发现，可见光诱导的SNC中间体可通过1,2-羰基加成被氟化酮捕获，从而获得安息香型产品。这一发现代表了亲核碳烯与酮反应的罕见例子，并提供了一种高效，用户友好且可扩展的方法来访问仅由光驱动的氟化叔醇衍生物，从而避免了使用外源催化剂或添加剂。

  DOI：

  10.1021/acs.orglett.1c00708

文献信息

• Diketo Compounds with (Trifluoromethyl)trimethylsilane:  Double Nucleophilic Trifluoromethylation Reactions
  作者：Rajendra P. Singh、Jeffry M. Leitch、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/jo0057304

  日期：2001.2.1

  Reactions of various diketo compounds with (trifluoromethyl)trimethylsilane (Me3SiCF3) in the presence of catalytic amounts of cesium fluoride have been studied. gamma -Ketoesters, CH3COCH2CH2CH2R (R = Et, Bu), were reacted with 2 equiv of Me3SiCF3 at room temperature to give CH3C(OH)(CF3)CH2CH2COCF3 in good yield after hydrolysis. alpha -Diketones, R1COCOR2 (R-1 = R-2 = Ph; R-1 = Ph, R-2 = Me; R-1 = R-2 = Me; R-1 = Me, R-2 = Et), when reacted with Me3SiCF3, formed 1:1 or 1:2 addition products depending on the reaction conditions and stoichiometry used. Reactions of diones CH3COXCOCH3 (X = -CH2CH2-, -C6H4C6H4-, -CH2-) with Me3SiCF3 also led to the formation of the mono- or diaddition products depending on reaction conditions. With various kinds of substituted arylglyoxals, 2 equiv of Me3SiCF3 produced monoaddition products in 70-75% yield and diaddition products in 5-10% yield. One of the monoalcohols and two of the diols have been characterized by single-crystal X-ray analysis, and the presence of inter- and intramolecular hydrogen bonding has been confirmed.
• Fluorinated Ketones as Trapping Reagents for Visible-Light-Induced Singlet Nucleophilic Carbenes
  作者：Daniel L. Priebbenow、Rowan L. Pilkington、Kyle N. Hearn、Anastasios Polyzos

  DOI：10.1021/acs.orglett.1c00708

  日期：2021.4.2

  Singlet nucleophilic carbenes (SNCs) containing only one heteroatom donor remain underutilized in chemical synthesis. We recently discovered that visible-light-induced SNC intermediates can be trapped by fluorinated ketones via 1,2-carbonyl addition to afford benzoin-type products. This discovery represents a rare example of nucleophilic carbenes reacting with ketones and delivers an efficient, user-friendly

  仅包含一个杂原子供体的单重亲核碳烯（SNC）在化学合成中仍未得到充分利用。我们最近发现，可见光诱导的SNC中间体可通过1,2-羰基加成被氟化酮捕获，从而获得安息香型产品。这一发现代表了亲核碳烯与酮反应的罕见例子，并提供了一种高效，用户友好且可扩展的方法来访问仅由光驱动的氟化叔醇衍生物，从而避免了使用外源催化剂或添加剂。