Diethyl 3-(trifluoromethyl)glutarate | 138852-02-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Diethyl 3-(trifluoromethyl)glutarate
• 英文别名: diethyl 3-(trifluoromethyl)pentanedioate；3-trifluoromethylglutaric acid diethyl ester
• CAS: 138852-02-5
• 化学式: C₁₀H₁₅F₃O₄
• 分子量: 256.222
• InChiKey: VTWOCWLXEBQQRD-UHFFFAOYSA-N

物化性质

• 沸点：
  95.1 °C
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diethyl 3-(trifluoromethyl)glutarate 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-(trifluoromethyl)pentane-1,5-diol
  参考文献：
  名称：

  PYRIMIDOPYRROLE SPIRO COMPOUNDS AND DERIVATIVES THEREOF AS DNA-PK INHIBITORS

  摘要：

  提供了一类DNA-PK抑制剂，具体而言，是由公式（III）表示的化合物或其药学上可接受的盐，以及在制备DNA-PK抑制剂相关药物时的使用。

  公开号：

  EP4063371A1
• 作为产物：
  描述：

  Diethyl 2-(ethoxycarbonyl)-3-(trifluoromethyl)glutarate 在 水 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 生成 Diethyl 3-(trifluoromethyl)glutarate
  参考文献：
  名称：

  PYRIMIDOPYRROLE SPIRO COMPOUNDS AND DERIVATIVES THEREOF AS DNA-PK INHIBITORS

  摘要：

  提供了一类DNA-PK抑制剂，具体而言，是由公式（III）表示的化合物或其药学上可接受的盐，以及在制备DNA-PK抑制剂相关药物时的使用。

  公开号：

  EP4063371A1

文献信息

• Highly Diastereoselective Michael Addition Reactions of Lithium Enolates to Ethyl 3-Trifluoromethylacrylate
  作者：Takashi Yamazaki、Jiro Haga、Tomoya Kitazume、Shinichiro Nakamura

  DOI：10.1246/cl.1991.2171

  日期：1991.12

  Michael addition reactions of lithium enolates derived from ketones, esters, and amides to ethyl 3-trifluoromethylacrylate were found to proceed smoothly in moderate to excellent chemical yields as well as with a high degree of diastereoselectivity at the newly formed carbon–carbon bond.

  发现来自酮、酯和酰胺的烯醇锂与 3-三氟甲基丙烯酸乙酯的迈克尔加成反应以中等至优异的化学产率顺利进行，并且在新形成的碳-碳键上具有高度的非对映选择性。
• Synthesis of 5-(trifluoromethyl)cyclohexane-1,3-dione and 3-amino-5-(trifluoromethyl)cyclohex-2-en-1-one: new trifluoromethyl building block
  作者：Olugbeminiyi O. Fadeyi、Cosmas O. Okoro

  DOI：10.1016/j.tetlet.2008.05.120

  日期：2008.8

  ne-1,3-dione and 3-amino-5-(trifluoromethyl)cyclohex-2-en-1-one from the sodium salt of methyl or ethyl-4-hydroxy-2-oxo-6-(trifluoromethyl)cyclohex-3-en-1-oate is demonstrated. The compounds represent highly functionalized reactive intermediates for the synthesis of organic and heterocyclic compounds containing a trifluoromethyl group.

  由甲基或乙基-4-羟基-2-钠盐简单合成5-（三氟甲基）环己烷-1,3-二酮和3-氨基-5-（三氟甲基）环己-2-烯-1-酮证实了氧代6-（三氟甲基）环己基-3-烯-1-酸酯。该化合物代表用于合成含有三氟甲基的有机和杂环化合物的高度官能化的反应性中间体。
• Synthesis of fluorinated cyclic s-trans vinylogous acid and amide ester derivatives
  作者：Cosmas O. Okoro、Olugbeminiyi O. Fadeyi、Patrice L. Jackson、Rhonda L. Richmond、Takeisha Farmer

  DOI：10.1016/j.tetlet.2006.08.046

  日期：2006.10

  procedure for the preparation of ethyl 4-amino-2-oxo-6-(trifluoromethyl)cyclohex-3-ene-1-carboxylate (enaminone) and methyl 4-hydroxy-2-oxo-6-(trifluoromethyl)cyclohex-3-ene-1-carboxylate (vinylogous acid) has been accomplished, using reactive Michael acceptors under basic condition. In addition, acyclic trifluoromethylated ester derivatives were isolated as competing by-products. The above compounds

  分两步制备4-氨基-2-氧代-6-（三氟甲基）环己-3-烯-1-羧酸乙酯（烯胺酮）和甲基4-羟基-2-氧代-6-（三氟甲基）乙酯使用碱性条件下的反应性迈克尔受体完成了环己-3-烯-1-羧酸（乙烯基酸）的合成。另外，分离出无环三氟甲基化酯衍生物作为竞争副产物。上述化合物代表新颖的合成上有用的三氟甲基构件。
• Herbicidal thiadiazabicyclodecanes
  申请人：Novartis Corporation

  公开号：US05817602A1

  公开（公告）日：1998-10-06

  Thiadiazabicyclodecanes of formula (I) wherein, Z is oxygen or sulfur; R is an optional substituent and W is an optionally condensed or substituted phenyl radical and the salts, complexes and stereisomers thereof, have good selective pre- and post-emergence herbicidal properties. ##STR1##

  公式（I）中的噻二唑双环癸烷，其中，Z为氧或硫；R为可选取代基团，W为可选缩合或取代的苯基基团，其盐类，配合物和立体异构体具有良好的选择性前后除草特性。
• Stereoselective Synthesis of Trifluoromethylated Compounds with Controlled Adjacent Tertiary Carbons by Michael Addition to (E)-3-(Trifluoromethyl)acrylates
  作者：Noriyasu Shinohara、Jiro Haga、Takashi Yamazaki、Tomoya Kitazume、Shinichiro Nakamura

  DOI：10.1021/jo00119a013

  日期：1995.7

  Michael addition reaction of various lithium enolates to ethyl (E)-3-(trifluoromethyl)acrylate (E)-1 was found to be one of the most effective routes to construct materials not only with a CF3 group but also with readily distinguishable multiple functionalities by the routine chemical transformations. Particularly, employment of lithium enolates from chiral acyloxazolidinones as Michael donors resulted in the formation of 1,4-adducts, usually with a high degree of diastereoselectivity as well as with a high degree of diastereofacial selectivities only in a single step. Further, it was suggested by both the experimental results and the ab initio calculations that interaction between fluorine-(s) and lithium strongly stabilized the present Michael intermediates, allowing for the smooth reactions even with ketone enolates under kinetically controlled conditions.