3-methoxybutan-2-one | 17742-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxybutan-2-one
• 英文别名: 3-methoxy-2-butanone；3-methoxy-butan-2-one；3-Methoxy-butan-2-on；Acetoin-methylaether；Methyl-(α-methoxy-aethyl)-keton；γ-Methoxy-β-oxo-butan
• CAS: 17742-05-1
• 化学式: C₅H₁₀O₂
• mdl: MFCD12062689
• 分子量: 102.133
• InChiKey: DLPGPGQJLPODMY-UHFFFAOYSA-N

物化性质

• 熔点：
  114 °C
• 沸点：
  87 °C(Press: 740 Torr)
• 密度：
  0.9063 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxybutan-2-one 在 Pt/Al₂O₃ 、 (-)-4-[(R)-((2S)-5-ethyl-1-azabicyclo[2.2.2]oct-2-yl)-methoxy-methyl]-quinoline 氢气 作用下， 以 溶剂黄146 为溶剂， 25.0 ℃ 、6.0 MPa 条件下， 反应 0.2h， 以20%的产率得到(+)-(2R,3S)-3-methoxy-2-butanol
  参考文献：
  名称：

  Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base

  摘要：

  The first successful example of the asymmetric hydrogenation of substituted a-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of < 50%. Addition of KOH gave a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of > 80% were obtained at > 95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.

  DOI：

  10.1002/1615-4169(200207)344:5<511::aid-adsc511>3.0.co;2-d
• 作为产物：
  描述：

  3-methoxybut-1-yne 在 硫酸 、 mercury(II) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 4.5h， 生成 3-methoxybutan-2-one
  参考文献：
  名称：

  Guillerm-Dron,D. et al., Bulletin de la Societe Chimique de France, 1973, p. 1417 - 1423

  摘要：

  DOI：

文献信息

• Aldol additions of pinacolone lithium enolate with ketones: reactivities governed predominantly by field effects
  作者：Goutam Das、Edward R. Thornton

  DOI：10.1021/ja00057a012

  日期：1993.2

  The relative reactivities of representative α- and β-heterosubstituted acyclic, cyclic (five- and six-membered), and aromatic ketones with the lithium enolate of pinacolone in diethyl ether at -78 o C were determined. The order of reactivitiesof monosubstituted acetones (MeCOCH 2 X) is X=Cl>OTBDMS>OMe>SMe>NMe 2 >CH 2 SM>H>Me and spans a range of 10 4

  测定了代表性的 α- 和 β- 杂取代的无环、环状（五元和六元）和芳香酮与频哪酮的烯醇锂在 -78 o C 的二乙醚中的相对反应性。单取代丙酮 (MeCOCH 2 X) 的反应性顺序为 X=Cl>OTBDMS>OMe>SMe>NMe 2 >CH 2 SM>H>Me，范围为 10 4
• Synthesis of <i>N</i>-Vinyl Nitrones via 1,4-Conjugate Elimination
  作者：Ryan E. Michael、Katelyn M. Chando、Tarek Sammakia

  DOI：10.1021/acs.joc.5b01138

  日期：2015.7.2

  A number of structurally and electronically diverse N-vinyl nitrones have been synthesized by a two-step method. The sequence consists of condensation of an α-chloroaldehyde or an α-phenoxy- or α-acetoxy ketone with a substituted benzyl hydroxylamine to provide the corresponding nitrone. Treatment of these species with a base induces a 1,4-elimination to provide the desired N-vinyl nitrone in good

  已经通过两步法合成了许多结构和电子上不同的N-乙烯基硝酮。该序列由α-氯醛或α-苯氧基-或α-乙酰氧基酮与取代的苄基羟胺的缩合以提供相应的硝酮组成。用碱处理这些物质可诱导1，4-消除，从而以良好或优异的产率提供所需的N-乙烯基硝酮。
• 3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents
  作者：Saimeng Jin、Fergal P. Byrne、James H. Clark、Con Robert McElroy、Alex Quinn、James Sherwood、Andrew J. Hunt

  DOI：10.1039/d1ra07322b

  日期：——

  3-methoxybutan-2-one (MO) was successfully evaluated as a bio-based solvent, while both Kamlet–Taft solvatochromic parameters and Hansen solubility parameters demonstrate its potential viability in the substitution of chlorinated solvents. MO exhibited a low peroxide forming potential and a negative Ames mutagenicity test and was successfully used as a solvent in a Friedel–Crafts acylation (79% yield compared to

  乙偶姻与碳酸二甲酯的甲基化是在可持续的一步工艺中进行的，与以前公布的方法相比，工艺质量强度 (PMI) 和原子经济性有所提高。所得产品 3-methoxybutan-2-one (MO) 被成功评估为生物基溶剂，而 Kamlet-Taft 溶剂致变色参数和 Hansen 溶解度参数均证明了其在替代氯化溶剂方面的潜在可行性。MO 表现出较低的过氧化物形成潜力和负的 Ames 致突变性测试，并成功地用作 Friedel-Crafts 酰化（产率为 79%，而二氯甲烷为 77%）和N-烷基化的溶剂。MO 是一种可再生的含氧溶剂，在某些应用中具有替代致癌卤代溶剂的潜力。
• Isolation, Structural Elucidation, and Absolute Stereochemistry of Enigmazole A, a Cytotoxic Phosphomacrolide from the Papua New Guinea Marine Sponge <i>Cinachyrella enigmatica</i>
  作者：Naoya Oku、Kentaro Takada、Richard W. Fuller、Jennifer A. Wilson、Megan L. Peach、Lewis K. Pannell、James B. McMahon、Kirk R. Gustafson

  DOI：10.1021/ja1016766

  日期：2010.8.4

  Enigmazole A (1), a novel phosphate-containing macrolide, was isolated from a Papua New Guinea collection of the marine sponge Cinachyrella enigmatica. The structure of 1, including the absolute stereochemistry at all eight chiral centers, was determined by a combination of spectroscopic analyses and a series of microscale chemical derivatization studies. Compound 1 is comprised of an 18-membered phosphomacrolide

  恩尼格唑 A (1) 是一种新型含磷酸盐的大环内酯，是从巴布亚新几内亚的海洋海绵 Cinachyrella enigmatica 中分离出来的。 1 的结构，包括所有八个手性中心的绝对立体化学，是通过光谱分析和一系列微观化学衍生化研究的结合来确定的。化合物 1 由 18 元磷大环内酯组成，其中含有嵌入的外亚甲基取代的四氢吡喃环和跨越嵌入的恶唑部分的无环部分。另外两个类似物，15-O-亚甲基唑 A 和 13-羟基-15-O-亚甲基唑 A，也被分离和指定。恩尼格唑是第一个来自海洋的磷大环内酯类化合物，在 NCI 60 细胞系抗肿瘤筛选中表现出显着的细胞毒性，平均 GI(50) 为 1.7 µM。
• Aromatic urea derivatives and their use as herbicide
  申请人：Mitsui Petrochemical Industries, Ltd.

  公开号：US04838924A1

  公开（公告）日：1989-06-13

  This invention relates to novel compounds of formula [I], a process for their production, and their use as a herbicide. ##STR1## wherein A represents the bond ##STR2## in which X is a hydrogen atom, a chlorine atom, a nitro group or a trifluoromethyl group; B represents a hydrogen atom, a methyl group or a methoxy group; and Ar represents one member selected from the group consisting of ##STR3## in which R.sup.1 to R.sup.38, are as defined hereinafter.

  本发明涉及一种新的化合物，其化学式为[I]，以及其制备方法和作为除草剂的用途。其中，A代表键结构##STR2## 其中X代表氢原子、氯原子、硝基或三氟甲基基团；B代表氢原子、甲基或甲氧基；Ar代表从以下组中选择的一种成员：##STR3## 其中，R^1至R^38如下所定义。