methyl 3-(furan-2-yl)-2-methyl-3-oxopropanoate | 85199-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(furan-2-yl)-2-methyl-3-oxopropanoate
• 英文别名: 3-[2]furyl-2-methyl-3-oxo-propionic acid methyl ester；3-[2]Furyl-2-methyl-3-oxo-propionsaeure-methylester
• CAS: 85199-55-9
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: DMJSPINWFQNGFI-UHFFFAOYSA-N

物化性质

• 沸点：
  114-116 °C(Press: 2 Torr)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(furan-2-yl)-2-methyl-3-oxopropanoate 反应 164.0h， 以28%的产率得到(R-(R^*,R^*))-β-hydroxy-α-methyl-2-furanpropanoate
  参考文献：
  名称：

  Furuichi, Akiya; Akita, Hiroyuki; Koshiji, Hiroko, Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 219 - 220

  摘要：

  DOI：
• 作为产物：
  描述：

  2-呋喃甲酰基乙酸甲酯 、 过氧化苯甲酸叔丁酯 在 copper(II) bis(tetrafluoroborate) 作用下， 以 水 、 氯苯 为溶剂， 反应 2.0h， 以57%的产率得到methyl 3-(furan-2-yl)-2-methyl-3-oxopropanoate
  参考文献：
  名称：

  tert-Butyl Peroxybenzoate-Promoted α-Methylation of 1,3-Dicarbonyl Compounds

  摘要：

  A tert-butyl peroxybenzoate (TBPB)-promoted direct a-methylation of 1,3-dicarbonyl compounds has been developed, providing alpha-methyl derivatives in moderate to good yields. In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator. This work represents a key complement to the traditional alpha-methylation of 1,3-dicarbonyl compounds using methyl iodide.

  DOI：

  10.1021/jo502204a

文献信息

• Heteroaryl Analogues of AMPA. 2. Synthesis, Absolute Stereochemistry, Photochemistry, and Structure−Activity Relationships
  作者：Erik Falch、Lotte Brehm、Ivan Mikkelsen、Tommy N. Johansen、Niels Skjærbæk、Birgitte Nielsen、Tine B. Stensbøl、Bjarke Ebert、Povl Krogsgaard-Larsen

  DOI：10.1021/jm9801206

  日期：1998.7.1

  7c (IC50 = 5.5 +/- 0.6 microM; EC50 = 96 +/- 5 microM) was shown to be markedly weaker than 7a (IC50 = 0.57 +/- 0.16 microM; EC50 = 7.4 +/- 0.2 microM) as an AMPA agonist, whereas 7b,d,e were inactive. The very potent AMPA agonist effect of 7f (IC50 = 0.15 +/- 0.03 microM; EC50 = 1.7 +/- 0. 2 microM) was shown to reside exclusively in 8 (IC50 = 0.11 +/- 0.01 microM; EC50 = 0.71 +/- 0.11 microM), whereas

  先前我们已经表明（S）-2-氨基-3-（3-羟基-5-苯基-4-异恶唑基）丙酸[（S）-APPA，2]是（RS）-2-的弱激动剂氨基-3-（3-羟基-5-甲基-4-异恶唑基）丙酸（AMPA）受体，被（S）-AMPA（1）特异性激活，而（S）-2-氨基-3- [3-羟基-5-（2-吡啶基）-4-异恶唑基]丙酸[[（S）-2-Py-AMPA，5]和（RS）-2-氨基-3- [3-羟基-5-（2-噻唑基）-4-异恶唑基]丙酸（4）是有效的AMPA激动剂。另一方面，（R）-APPA（3）和（R）-2-Py-AMPA（6）被证明是弱AMPA拮抗剂。现在，我们报告了2-Py-AMPA（7a）和异构体化合物3-Py-AMPA（7b）和4-Py-AMPA（7c）以及7a类似物（RS）-2-amino-的合成3- [3-羟基-5-（6-甲基-2-吡啶基）-4-异恶唑基]丙酸（7d）和（RS）-2-氨基-3-
• Reductive Reformatsky-Honda Reaction of α,β-Unsaturated Esters: Facile Formation of 1,3-Dicarbonyl Compounds and β-Hydroxy Esters
  作者：Kazuyuki Sato、Motoyuki Isoda、Shizuka Ohata、Shuhei Morita、Atsushi Tarui、Masaaki Omote、Itsumaro Kumadaki、Akira Ando

  DOI：10.1002/adsc.201100463

  日期：2012.2

  The reaction of tris(triphenylphosphine)rhodium chloride [RhCl(PPh3)3] with diethylzinc (Et2Zn) easily afforded a rhodium-hydride complex that effects the 1,4-reduction of α,β-unsaturated esters to give rhodium enolates. Formation of the rhodium enolate is followed by transmetalation with the zinc species to give a Reformatsky-type reagent, and this reacts with various acid chlorides at the α-position

  三（三苯基膦）氯化铑[RhCl（PPh 3）3 ]与二乙基锌（Et 2 Zn）的反应容易得到氢化铑络合物，该络合物可实现α，β-不饱和酯的1,4-还原，从而得到烯醇铑。 。形成烯醇铑后，与锌物种进行金属转移以形成Reformatsky型试剂，该试剂在α位与各种酰氯反应生成β-酮酸酯。Reformatsky型试剂还可以与各种亲电子试剂（如醛，酮和酸酐）反应，得到相应的产物，其中亲电试剂在α，β-不饱和酯的α-位被还原性引入。
• The use of microorganisms in organic synthesis. III. Microbiological asymmetric reduction of methyl 3-(2-furyl)-2-methyl-3-oxopropionate.
  作者：HIROYUKI AKITA、AKIYA FURUICHI、HIROKO KOSHIJI、KOKI HORIKOSHI、TAKESHI OISHI

  DOI：10.1248/cpb.32.1333

  日期：——

  Microbiological asymmetric reduction of methyl 3-(2-furyl)-2-methyl-3-oxopropionate (5) by various yeasts was carried out. Four kinds of methyl 3-(2-furyl)-3-hydroxy-2-methyl propionates (6a-6d) could be obtained separately from the prochiral β-keto ester 5 by reduction with properly selected microorganisms. In particular, the desired syn-isomer 6a was obtained with high optical purity (>99% e.e.). Both the chemical yield and the optical purity of the reduction products (6a-6d) were significantly improved when fermentation was carried out on a large scale using a 30 1 jar fermentor or a 200 1 tank.

  对甲基3-(2-呋喃基)-2-甲基-3-氧代丙酸酯（5）进行了微生物不对称还原。通过用适当选择的微生物进行还原，可以从手性前体β-酮酯5中分别得到四种甲基3-(2-呋喃基)-3-羟基-2-甲基丙酸酯（6a-6d）。特别是，所希望的顺式异构体6a获得了高光学纯度（>99% e.e.）。当使用30 1罐发酵器或200 1罐进行大规模发酵时，还原产物（6a-6d）的化学产率和光学纯度都得到了显著提高。
• Rhodium-catalyzed hydroaroylation of α,β-unsaturated esters using aroyl chlorides and Et2MeSiH
  作者：Takako Muraoka、Eiji Hiraiwa、Minami Abe、Keiji Ueno

  DOI：10.1016/j.tetlet.2013.06.009

  日期：2013.8

  Hydroaroylation of methyl acrylate 2a to give the alpha-aroyl esters 4 took place in the three-component reaction of 2a, aroyl chlorides 1, and Et2MeSiH in the presence of 1 mol % of [Rh(cod)(PR3)2]OTf (cod = 1,5-cyclooctadiene, OTf = OSO2CF3, R = Ph (3a), OPh (3b)) in CH2Cl2. GC and H-1 NMR investigation revealed that the rhodium-catalyzed hydroaroylation proceeds via two successive transformations, that is, hydrosilylation of 2a to afford silyl enol ether 5a followed by C-C bond formation between 5a and 1a. (C) 2013 Elsevier Ltd. All rights reserved.
• Studies in Mixed Ester Condensations. III
  作者：E. Earl Royals、Derek G. Turpin

  DOI：10.1021/ja01650a057

  日期：1954.11