methyl-d₃ benzoate | 79825-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl-d₃ benzoate
• 英文别名: methyl benzoate-d₃；Benzoesaeure-trideuterio-methylester；Trideuteromethyl benzoate；trideuteriomethyl benzoate
• CAS: 79825-70-0
• 化学式: C₈H₈O₂
• 分子量: 139.126
• InChiKey: QPJVMBTYPHYUOC-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醇 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 氯化苄 、 4-甲基氯苄 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 methyl-d₃ benzoate
  参考文献：
  名称：

  共价结合的苄基配体促进醇对钯的选择性钯催化氧化酯化反应

  摘要：

  这是一个苄种魔：在与苄基氯的标题反应的进行作为氧化剂时，苄基作为配位体的碳，从而具有η 3上钯-coordination效果（参见方案）。各种醛和醇以良好或优异的收率选择性地转化为相应的酯。

  DOI：

  10.1002/anie.201201960

文献信息

• Highly effective C–C bond cleavage of lignin model compounds
  作者：Yinling Wang、Qianyi Wang、Jianghua He、Yuetao Zhang

  DOI：10.1039/c7gc00844a

  日期：——

  active ester bond through the classic organic name reaction, Baeyer–Villiger (BV) oxidation, and thus acetal esters and aryl esters were produced in high yields (up to 99%) at room temperature. Next, K2CO3 catalyzed the alcoholysis of the resulting ester products at 45 °C, affording various useful chemical platforms in excellent yields (up to 99%), such as phenols and multifunctional esters. This method

  开发了一种用于木质素模型化合物的C–C键裂解的高效方法。惰性Ç α -C β或C α -C苯基的氧化木质素模型化合物通过键的经典有机名称反应成功地转化为活性酯键，拜尔-维利格（BV）的氧化，因此缩醛酯和芳基酯是在室温下以高收率（高达99％）生产。接下来，K 2 CO 3催化所得酯产物在45°C下的醇解反应，从而以优异的收率（高达99％）提供了各种有用的化学平台，例如苯酚和多功能酯。该方法使用可商购的试剂，不含过渡金属且简单，但高效，并且涉及温和的反应条件。
• General and Selective Palladium-Catalyzed Oxidative Esterification of Alcohols
  作者：Saravanan Gowrisankar、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.201008035

  日期：2011.5.23

  Selectively esterified: Primary alcohols react with dioxygen as a benign oxidant in a palladium‐catalyzed oxidative esterification (see scheme). The corresponding aldehydes and esters are formed highly selectively depending on the catalyst system. The reactions take place in the presence of commercially available ligands without the need for additional organic hydrogen acceptors.

  选择性酯化：在钯催化的氧化酯化反应中，伯醇与作为良性氧化剂的双氧反应（请参阅方案）。取决于催化剂体系，高度选择性地形成相应的醛和酯。该反应在可商购的配体存在下进行，而无需另外的有机氢受体。
• Efficient and selective palladium-catalyzed direct oxidative esterification of benzylic alcohols under aerobic conditions
  作者：Yongke Hu、Bindong Li

  DOI：10.1016/j.tet.2017.11.025

  日期：2017.12

  A highly efficient palladium-catalyzed approach for the direct oxidative esterification of benzylic alcohols with methanol and long-chain aliphatic alcohols under mild conditions has been achieved. This practical catalyst system exhibits a broad substrate scope and good functional group tolerance. Catalytic amount of Bi(OTf)3 is used as co-catalyst to improve the activity and selectivity of the reactions

  已经实现了在温和条件下用甲醇和长链脂族醇将苄醇直接氧化酯化的高效钯催化方法。这种实用的催化剂体系具有广泛的底物范围和良好的官能团耐受性。催化量的Bi（OTf）3用作助催化剂，以提高反应的活性和选择性。获得了多种酯，产率为43–96％。
• Oxygen‐Controlled Catalysis by Vitamin B ₁₂ ‐TiO ₂ : Formation of Esters and Amides from Trichlorinated Organic Compounds by Photoirradiation
  作者：Hisashi Shimakoshi、Yoshio Hisaeda

  DOI：10.1002/anie.201507782

  日期：2015.12.14

  An oxygen switch in catalysis of the cobalamin derivative (B12)‐TiO2 hybrid catalyst for the dechlorination of trichlorinated organic compounds has been developed. The covalently bound B12 on the TiO2 surface transformed trichlorinated organic compounds into an ester and amide by UV light irradiation under mild conditions (in air at room temperature), while dichlorostilbenes (E and Z forms) were formed

  已经开发出了钴巴拉明衍生物（B 12）-TiO 2杂化催化剂催化三氯代有机化合物脱氯的氧开关。在温和的条件下（在室温下在空气中），通过紫外线照射，在TiO 2表面上共价结合的B 12将三氯化有机化合物转化为酯和酰胺，而二氯代对苯二酚（E和Z在氮气中由三氯化苯形成。苯甲酰氯形成为酯和酰胺的中间体，通过GC-MS检测。合成策略的底物范围已通过各种三氯化有机化合物的范围得到证明。利用TiO 2的孔和导带电子，一种相片二重唱反应2在乙12 -TiO 2的酰胺形成也被开发。
• Efficient, scalable and economical preparation of tris(deuterium)- and¹³C-labelled<i>N</i>-methyl-<i>N</i>-nitroso-<i>p</i>-toluenesulfonamide (Diazald®) and their conversion to labelled diazomethane
  作者：Samuel W. J. Shields、Jeffrey M. Manthorpe

  DOI：10.1002/jlcr.3231

  日期：2014.10

  A method for the preparation of multi-gramme quantities of N-methyl-d3-N-nitroso-p-toluenesulfonamide (Diazald-d3) and N-methyl-13C-N-nitroso-p-toluenesulfonamide (Diazald-13C) and their conversion to diazomethane-d2 and diazomethane-13C, respectively, is presented. This approach uses robust and reliable chemistry, and critically, employs readily commercially available and inexpensive methanol as the label source. Several reactions of labelled diazomethane are also reported, including alkene cyclopropanation, phenol methylation and α-diazoketone formation, as well as deuterium scrambling in the preparation of diazomethane-d2 and subsequent methyl esterification of benzoic acid.

  本文介绍了一种制备多克量N-甲基-d3-N-亚硝基对甲苯磺酰胺（Diazald-d3）和N-甲基-13C-N-亚硝基对甲苯磺酰胺（Diazald-13C）及其分别转化为重氮甲烷-d2和重氮甲烷-13C的方法。该方法采用稳健可靠的化学反应，关键在于使用易于商业获取且价格低廉的甲醇作为标记源。此外，还报道了标记重氮甲烷的几种反应，包括烯烃环丙烷化、苯酚甲基化和α-重氮酮的形成，以及在制备重氮甲烷-d2过程中氘的交换，随后对苯甲酸进行甲酯化。