甲基丙烯酸甲酯-D8 | 35233-69-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基丙烯酸甲酯-D8
• 中文别名: 甲基丙烯酸甲酯-d8
• 英文名称: d₈-methyl methacrylate
• 英文别名: methyl methacrylate-d₈；[2H3]-methyl [2H5]-methacrylate；deuterated methyl methacrylate；d8-methyl methacrylate；methyl methacrylate-d8；3,3-dideuterio-2-trideuteriomethyl-acrylic acid trideuteriomethyl ester；Perdeutero(methyl methacrylate)；trideuteriomethyl 3,3-dideuterio-2-(trideuteriomethyl)prop-2-enoate
• CAS: 35233-69-3
• 化学式: C₅H₈O₂
• 分子量: 108.054
• InChiKey: VVQNEPGJFQJSBK-MGGKGRBPSA-N

物化性质

• 熔点：
  -48 °C (lit.)
• 沸点：
  100 °C (lit.)
• 密度：
  1.011 g/mL at 25 °C
• 闪点：
  50 °F
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  F,Xi
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1247 3
• 安全说明：
  S24,S37,S46
• WGK Germany：
  1
• 储存条件：
  存放在0至6°C的阴凉干燥处。

反应信息

• 作为反应物：
  描述：

  甲基丙烯酸甲酯-D8 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Formation Pathways of Ethyl Esters of Branched Short-Chain Fatty Acids during Wine Aging

  摘要：

  The particular behavior during wine aging of fermentative branched fatty acid ethyl esters, related to yeast nitrogen metabolism, compared that of their straight-chain analogues, related to yeast lipid metabolism, was first checked in 1-5 year aged Muscadet wines. Quantitative SIDA measurements showed that the levels of the former increased, whereas those of the latter decreased. Then, three hypothetical pathways suggested in the literature to explain these variations of branched esters were investigated. Two Muscadet and Sylvaner wines were spiked with levels of deuterated isobutanoic acid and its ethyl ester, similar to those of their natural analogues, then they were submitted to model aging. Quantitative SIDA measurements on the formation of these natural and labeled ethyl esters from the corresponding acids revealed that the behavior of the natural and labeled compounds were similar. The acid levels were much higher than the ester levels in the initial young wine, and a significant upward trend of their esterification ratios to those of the acid-ester equilibrium was observed with aging. Thus, this equilibrium proved to be the most effective in generating the branched fatty acid ethyl esters during wine aging. In contrast, the formation of these acids by Strecker-type degradation of wine amino acids in the conditions of the model aging or by hydrolysis of their glycoconjugates proved to be ineffective.

  DOI：

  10.1021/jf048157o
• 作为产物：
  描述：

  2-[2H3]methyl-2-(phenylsulfinyl)-[3,3,3-2H3]propionoic acid, methyl ester 以85%的产率得到甲基丙烯酸甲酯-D8
  参考文献：
  名称：

  Synthesis of [13C] and [2H] susbstituted methacrylic acid, [13C] and [2H] substituted methyl methacrylate and/or related compounds

  摘要：

  本发明涉及公式的标记化合物，其中Q从所述组中选择，所述组由—S—、—S(═O)—和—S(═O)2—组成，Z从所述组中选择，所述组由1-萘基、取代的1-萘基、2-萘基、取代的2-萘基和苯基与结构的取代物组成，其中R1、R2、R3、R4和R5各自独立地从氢、C1-C4低烷基、卤素和NH2、NHR和NRR'组成的氨基团中选择，其中R和R'各自独立地从C1-C4低烷基、芳基和烷氧基组成的组中选择，X从氢、C1-C4低烷基和全氘代C1-C4低烷基组成的组中选择。本发明还涉及制备标记化合物的方法，例如通过将(CH3CH2O—13C(O)—13CH2)—芳基砜前体与13CHI反应以形成(CH3CH2O—13C(O)—13C(13CH3)2)—芳基砜中间体，并且通过将(CH3CH2O—13C(O)—13C(13CH3)2)—芳基砜中间体与氢氧化钠反应，随后酸化以形成[13C]丙烯酸的制备过程。本发明还涉及制备[2H8]甲基丙烯酸甲酯的方法，通过将(HOOC—C(C2H3)2—芳基亚砜中间体与CD3I反应以形成(2H3COOC—C(C2H3)2)—芳基亚砜中间体，并且在足够温度和时间下加热(2H3COOC—C(C2H3)2)—芳基亚砜中间体以形成[2H8]甲基丙烯酸甲酯。

  公开号：

  US20070106085A1

文献信息

• Modulators of Cystic Fibrosis Transmembrane Conductance Regulator
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20160095858A1

  公开（公告）日：2016-04-07

  The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

  本发明涉及一种具有以下化学式I的化合物： 或其药用可接受的盐，其中R 1 ，R 2 ，R 3 ，W，X，Y，Z，n，o，p和q在此处定义，用于治疗CFTR介导的疾病，如囊性纤维化。本发明还涉及药物组合物、治疗方法和相关工具包。
• Rh(I)–Bisphosphine-Catalyzed Asymmetric, Intermolecular Hydroheteroarylation of α-Substituted Acrylate Derivatives
  作者：Claire M. Filloux、Tomislav Rovis

  DOI：10.1021/ja511445x

  日期：2015.1.14

  Asymmetric hydroheteroarylation of alkenes represents a convenient entry to elaborated heterocyclic motifs. While chiral acids are known to mediate asymmetric addition of electron-rich heteroarenes to Michael acceptors, very few methods exploit transition metals to catalyze alkylation of heterocycles with olefins via a C–H activation, migratory insertion sequence. Herein, we describe the development

  烯烃的不对称氢杂芳基化代表了复杂杂环基序的便捷进入。虽然已知手性酸可以介导富电子杂芳烃向 Michael 受体的不对称加成，但很少有方法利用过渡金属通过 C-H 活化、迁移插入序列催化杂环与烯烃的烷基化。在此，我们描述了α-取代丙烯酸酯与苯并恶唑的不对称分子间氢杂芳基化反应的发展。该反应以中等至优异的产率和良好至优异的对映选择性提供2-取代的苯并恶唑。值得注意的是，一系列机制研究似乎与涉及 Rh(I)-烯醇化物对映选择性质子化的途径相矛盾，尽管事实上在芳基硼酸与甲基丙烯酸酯衍生物的相关加成中几乎一致地调用了这种机制。相反，有证据表明，迁移插入或β-氢化物消除具有对映决定性，Rh(I)-烯醇化物异构化为Rh(I)-杂苄基物质可将所得的α-立构中心与差向异构化隔离开来。庞大的配体 CTH-(R)-Xylyl-P-Phos 对于反应性和对映选择性至关重要，因为它可能会阻止苯并恶唑底物或中间体与循
• 13C chemical shift non-equivalence in methylene carbons of monosubstituted cyclohexanes
  作者：Hiroshi Ito、Alfred F. Renaldo、Robert D. Johnson、Mitsuru Ueda

  DOI：10.1002/mrc.1260270315

  日期：1989.3

  Monosubstituted cyclohexanes were synthesized by addition of a cyclohexyl radical to olefins bearing different substituents at the α‐position. Six distinct methylene 13C resonances were observed, indicating that the methylene carbons located at the 2 and 6 positions and at the 3 and 5 positions are not magnetically equivalent. This magnetic non‐equivalence (anisochronism) observed in the monosubstituted

  单取代的环己烷是通过将环己基加成到 α 位具有不同取代基的烯烃上来合成的。观察到六个不同的亚甲基 13C 共振，表明位于 2 和 6 位以及 3 和 5 位的亚甲基碳不是磁等效的。在单取代的环己烷中观察到的这种磁性非等价性（不等时性）是由于将不对称中心 β 引入前手性 C-1 环碳。
• 重水素化メタクリル酸メチルの製造方法
  申请人：——

  公开号：JP2005082487A

  公开（公告）日：2005-03-31

  PROBLEM TO BE SOLVED: To provide an economical manufacturing method of methyl methacrylate-d8 (C5D8O2) which is excellent in both the deuteration rate and the chemical purity and is useful as a raw material for plastic optical fibers and optical waveguide materials having a low transmission loss.

  SOLUTION: Methyl methacrylate-d8 is manufactured using as raw materials readily available methanol-d4 and acetone-d6 with all hydrogen atoms thereof deuterated, where methanol-d4 is converted into methanol-d3 with its methyl group fully deuterated and methyl methacrylate-d8 is obtained from the thus-obtained methanol-d3 with its methyl group fully deuterated and acetone cyanhydrin-d6 prepared from acetone-d6. A deuterium-containing compound, recovered when methanol-d4 is converted into methanol-d3 with its methyl group fully deuterated, is reutilized as a part of raw materials for manufacturing methanol-d4 and acetone-d6.

  COPYRIGHT: (C)2005,JPO&NCIPI

  解决的问题：提供一种经济的甲基丙烯酸-d8（C5D8O2）的制造方法，该方法在氘化率和化学纯度方面均优异，并且可用作塑料光纤和光波导材料的原材料，具有低传输损耗。

  解决方案：使用易获得的甲醇-d4和丙酮-d6作为原料制造甲基丙烯酸-d8，其中所有氢原子均被氘代替，其中甲醇-d4被转化为其甲基完全氘代的甲醇-d3，然后从得到的甲醇-d3中获得其甲基完全氘代的甲基丙烯酸-d8，并使用从丙酮-d6制备的丙酮氰醇-d6。当甲醇-d4转化为其甲基完全氘代的甲醇-d3时，回收的含氘化合物被重新利用作为制造甲醇-d4和丙酮-d6的部分原料。

  版权所有：（C）2005，JPO&NCIPI

• Experimental Mechanistic Studies of the Tail-to-Tail Dimerization of Methyl Methacrylate Catalyzed by N-Heterocyclic Carbene
  作者：Terumasa Kato、Yoshiya Ota、Shin-ichi Matsuoka、Koji Takagi、Masato Suzuki

  DOI：10.1021/jo401477b

  日期：2013.9.6

  We and others have previously reported the intermolecular umpolung reactions of Michael acceptors catalyzed by an N-heterocyclic carbene (NHC). The representative tail-to-tail dimerization of methyl methacrylate (MMA) has now been intensively investigated, leading to the following conclusions: (1) The catalysis involves the deoxy-Breslow intermediate, which is quite stable and remains active after

  我们和其他人先前已经报道了由N-杂环卡宾（NHC）催化的Michael受体的分子间蛋白空反应。现已对代表性的甲基丙烯酸甲酯（MMA）的尾到尾二聚化进行了深入研究，得出以下结论：（1）催化过程涉及脱氧-布雷斯洛中间体，该中间体非常稳定，在催化后仍保持活性。（2）将中间体加入MMA并最终消除催化剂是限速步骤。将NHC添加到MMA中和质子转移相对非常快。（3）第一MMA的两个烯基质子经历分子间转移至二聚体的C3和C5。（4）初始质子转移是分子间的。（5）与安息香缩合相比，动力学，可逆性明显不同，