ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate | 85515-84-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate
• 英文别名: (RS)-ethyl 2,4,4-trimethyl-3-oxovalerate；2,4,4-trimethyl-3-oxo-valeric acid ethyl ester；2,4,4-Trimethyl-3-oxo-valeriansaeure-aethylester；Ethyl 2,4,4-trimethyl-3-oxopentanoate
• CAS: 85515-84-0
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: OXHBIQUYDSLUAH-UHFFFAOYSA-N

物化性质

• 沸点：
  103-105 °C(Press: 19 Torr)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate 在 sodium hydroxide 、 盐酸羟胺 作用下， 反应 1.67h， 以75%的产率得到3-hydroxy-4-methyl-5-tert-butylisoxazole
  参考文献：
  名称：

  Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors

  摘要：

  The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) to rat brain synaptic membranes. These data were compared with the earlier reported effects of the compounds on single neurons in the feline spinal cord obtained by microelectrophoretic techniques. The three compounds AMPA, ATPA, and ABPA are agonists at the class of receptors assumed to represent a subtype of physiological (S)-glutamic acid (Glu) receptors. Inhibition of [3H]AMPA binding by ATPA was 1 order of magnitude weaker than that of AMPA, in agreement with the relative potency of these compounds in vivo. ABPA proved to be equipotent with AMPA both as an inhibitor of AMPA binding and as a neuronal excitant. The compounds 8, 15a, and 15b have no effect as inhibitors of AMPA binding, in agreement with in vivo studies that have shown that 8 does not affect the firing of central neurons whereas 15a and 15b are antagonists at NMDA receptors, a subpopulation of excitatory receptors not affected by AMPA. Molecular mechanical calculations on AMPA, ATPA, and ABPA using the program MM2 showed that conformations of AMPA, ABPA, and especially ATPA by rotation of the amino acid side chain have energy barriers. A possible receptor-active conformation is suggested.

  DOI：

  10.1021/jm50001a022
• 作为产物：
  描述：

  丙酸乙酯 在 Jones’ reagent 作用下， 以 丙酮 为溶剂， 生成 ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate
  参考文献：
  名称：

  氯化锰（II）或四丁基硼氢化铵催化的硼氢化钠立体选择性还原2-甲基-3-氧代酯（或酰胺）。实用的赤型和苏型-3-羟基-2-甲基酯（或酰胺）的制备方法

  摘要：

  赤-3-羟基-2- methylpropionates或赤-3-羟基-2-甲基丙酰胺用高立体选择性加入NaBH制备4减少在相应的2-甲基-3-氧代酯或2-甲基-3-氧代酰胺的催化量的氯化锰（II）的存在。另一方面，用n -Bu 4 NBH 4还原这些底物选择性地提供了苏式异构体。还描述了在1N HCl-MeOH中用NaBH 3 CN对2-甲基-3-氧代酰胺的赤型选择性还原。

  DOI：

  10.1016/s0040-4020(01)81804-4

文献信息

• Sulfur-Extrusive Rearrangement of α-Acylthio Ester by Lithium Amide
  作者：Kazuo Tsuzuki、Masaharu Akeyoshi、Satoshi Omura

  DOI：10.1246/bcsj.58.395

  日期：1985.1

  α-Acylthio esters readily undergo facile rearrangement to give β-keto esters on treatment with lithium amide at −78°C. Thiolactone 3, a key intermediate for thiolactonic antibiotics, was synthesize...

  在 -78°C 下用氨基锂处理后，α-酰基硫酯很容易发生重排，得到 β-酮酯。硫内酯类抗生素的关键中间体硫内酯 3 正在合成...
• A practical and stereoselective reduction of 3-keto-2-methyl esters or 3-keto-2-methyl amides into erythro-3-hydroxy-2-methyl esters or erythro-3-hydroxy-2-methyl amides with NaBH4 catalyzed by MnCl2
  作者：Hideaki Fujii、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/0040-4039(91)80775-2

  日期：1991.10

  Erythro-3-hydroxy-2-methylpropionates or erythro-3-hydroxy-2-methylpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 3-keto esters or 3-keto amides in the presence of a catalytic amount of MnCl2.

  在催化量的MnCl 2存在下，通过NaBH 4还原相应的3-酮基酯或3-酮基酰胺，以高立体选择性制备赤型-3-羟基-2-甲基丙酸酯或赤型3-羟基-2-甲基丙酰胺。。
• Isoxazol-5(4H)-ones. X-Ray crystal structures of a 4-hydroxyisoxazol-5(4H)-one and a [4,4′-biisoxazole]-5(4H),5′(4′H)-dione formed by oxygen oxidation of 3-tert-butyl-4-methylisoxazol-5(4H)-one
  作者：Lotte Brehm、Jørgen S. Johansen、Povl Krogsgaard-Larsen

  DOI：10.1039/p19920002059

  日期：——

  (2H)-one 6 and (RS)-3-tert-butyl-4-methylisoxazol-5(4H)-one 7. During the attempts to crystallize the inseparable mixture of tautomers 6 and 7 two other compounds, (RS)-3-tert-butyl-4-hydroxy-4-methylisoxazol-5(4H)-one 8 and (RS,RS)-3,3′-di-tert-butyl-4,4′-dimethyl-[4,4′-biisoxazole]-5(4H), 5′(4H)-dione 9, were progressively formed. The structures of compounds 8 and 9 were established by X-ray analyses

  乙基的处理（RS）-2,4,4-三甲基-3-氧代戊酸酯4在碱性条件下的羟胺，得到5-叔丁基-4-甲基异恶唑-3-醇5和3-互变异构体混合物叔丁基- 4-甲基异恶唑-5（2 H）-one 6和（RS）-3-叔丁基-4-甲基异恶唑-5（4 H）-one 7。在尝试使互变异构体6和7的不可分离的混合物结晶的过程中，出现了另外两种化合物（（RS）-3-叔丁基-4-羟基-4-甲基异恶唑-5（4 H）-8和（RS，RS）-3,3'-二叔丁基-4,4'-二甲基-[4,4'-联异唑] -5（4 H），5'（4 H）-二酮9，逐渐形成。通过X射线分析确定化合物8和9的结构。提出化合物8和9是通过用氧气氧化化合物7而形成的，但是这两个氧化过程的机理尚不清楚。
• Catalyst modifiers and their use in the polymerization of olefin(s)
  申请人：——

  公开号：US20040106751A1

  公开（公告）日：2004-06-03

  The present invention relates to the use of thermally triggered compounds that when used with a polymerization catalyst in a polymerization process results in the controllable generation of one or more catalyst inhibitors that renders the polymerization catalyst substantially or completely inactive.

  本发明涉及使用热触发化合物，与聚合催化剂一起在聚合过程中使用，从而可控地生成一个或多个催化剂抑制剂，使聚合催化剂几乎或完全失活。
• Components and Catalysis for the Polymerization of Olefins
  申请人：Gulevich Yuri

  公开号：US20070208150A1

  公开（公告）日：2007-09-06

  The present invention relates to a solid catalyst component for the polymerization of olefins CH 2 =CHR in which R is hydrogen or a hydrocarbon radical with 1-12 carbon atoms, comprising Mg, Ti, halogen and an electron donor selected from β-keto-ester derivatives of a particular formula. Said catalyst components when used in the polymerization of olefins, and in particular of propylene, are capable to give polymers in high yields and with high isotactic index expressed in terms of high xylene insolubility.

  本发明涉及一种用于聚合烯烃CH2 = CHR的固体催化剂组分，其中R为氢或具有1-12个碳原子的烃基，包括Mg、Ti、卤素和从特定公式中选择的β-酮酸酯衍生物的电子给体。当在聚合烯烃，特别是丙烯的聚合中使用该催化剂组分时，能够以高收率和高异构指数的形式给出聚合物，表现为高二甲苯不溶性。