(phenyl-4-d)methanol | 13122-27-5

• 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: (phenyl-4-d)methanol
• 英文别名: (4-Deuteriophenyl)methanol
• CAS: 13122-27-5
• 化学式: C₇H₈O
• 分子量: 109.132
• InChiKey: WVDDGKGOMKODPV-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (phenyl-4-d)methanol 以 二甲基亚砜 为溶剂， 反应 120.0h， 生成 dibenzyl-4,4'-d2 ether
  参考文献：
  名称：

  Skeletal rearrangements on chemical ionization of dibenzyl ether and derivatives

  摘要：

  AbstractProtonated molecular ions of dibenzyl ether, formed by chemical ionization using hydrogen and isobutane as reagent gases, undergo skeletal rearrangements to lose water and formaldehyde, both in the ion source and the flight path. The rearrangements have been elucidated by deuterium labelling and chemical substitution. The water lost contains the reagent proton and an aromatic hydrogen atom, and the aromatic hydrogen atoms have been shown to be mobile prior to the reaction. It is proposed that the skeletal rearrangement for water loss is initiated by protonation on the ether oxygen atom, followed by benzyl migration. The formaldehyde lost contains benzylic hydrogen atoms exclusively, and it is proposed that the skeletal rearrangement is preceded by hydrogen rearrangement of an oxygen protonated molecular ion to a ring protonated molecular ion. Daughter ion structures are supported by comparisons of their collision induced dissociation spectra with those of isomeric ions prepared by alternative routes.

  DOI：

  10.1002/oms.1210161003
• 作为产物：
  描述：

  苯佐卡因 在 lithium aluminium tetrahydride 、 deuteriohypophosphorous acid 、 sodium nitrite 作用下， 生成 (phenyl-4-d)methanol
  参考文献：
  名称：

  Skeletal rearrangements on chemical ionization of dibenzyl ether and derivatives

  摘要：

  AbstractProtonated molecular ions of dibenzyl ether, formed by chemical ionization using hydrogen and isobutane as reagent gases, undergo skeletal rearrangements to lose water and formaldehyde, both in the ion source and the flight path. The rearrangements have been elucidated by deuterium labelling and chemical substitution. The water lost contains the reagent proton and an aromatic hydrogen atom, and the aromatic hydrogen atoms have been shown to be mobile prior to the reaction. It is proposed that the skeletal rearrangement for water loss is initiated by protonation on the ether oxygen atom, followed by benzyl migration. The formaldehyde lost contains benzylic hydrogen atoms exclusively, and it is proposed that the skeletal rearrangement is preceded by hydrogen rearrangement of an oxygen protonated molecular ion to a ring protonated molecular ion. Daughter ion structures are supported by comparisons of their collision induced dissociation spectra with those of isomeric ions prepared by alternative routes.

  DOI：

  10.1002/oms.1210161003

文献信息

• Chemo- and Regioselective Direct Hydroxylation of Arenes with Hydrogen Peroxide Catalyzed by a Divanadium-Substituted Phosphotungstate
  作者：Keigo Kamata、Taiyo Yamaura、Noritaka Mizuno

  DOI：10.1002/anie.201201605

  日期：2012.7.16

  Peroxide in, phenol out: The catalyst [γ‐PW10O38V2(μ‐OH)2]3− showed high activity in the hydroxylation of various aromatic compounds with aqueous H2O2. The system was regioselective, producing para‐phenols from monosubstituted benzene derivatives. Furthermore, alkylarenes with reactive side‐chain CH bonds could be chemoselectively hydroxylated without significant formation of side‐chain oxygenated

  过氧化物，酚出：将催化剂[γ-PW 10 ö 38 V 2（μ-OH）2 ] 3-表明在各种芳族化合物与水性小时羟化活性高2 Ò 2。该系统具有区域选择性，可从单取代的苯衍生物生产对酚。此外，反应性侧链的C烷基芳烃 H键可以化学选择性羟基化而不显著形成的侧链氧化产物。
• Development of Highly Chemoselective Bulky Zincate Complex,<i>t</i>Bu₄ZnLi₂: Design, Structure, and Practical Applications in Small-/Macromolecular Synthesis
  作者：Taniyuki Furuyama、Mitsuhiro Yonehara、Sho Arimoto、Minoru Kobayashi、Yotaro Matsumoto、Masanobu Uchiyama

  DOI：10.1002/chem.200800536

  日期：2008.11.17

  We present full details of the unique reactivities of the newly developed dianion-type bulky zincate, dilithium tetra-tert-butylzincate (tBu(4)ZnLi(2)). With this reagent, halogen-zinc exchange reaction of variously functionalized haloaromatics and anionic polymerization of N-isopropylacrylamide (NIPAm)/styrene with excellent chemoselectivity were realized. Halogen-zinc exchange reaction followed by

  我们介绍了新开发的二价阴离子型大体积锌酸盐，四叔丁基锌酸二锂（tBu（4）ZnLi（2））的独特反应性的完整细节。用这种试剂，实现了具有多种化学官能度的各种官能化卤代芳烃的卤素-锌交换反应和N-异丙基丙烯酰胺（NIPAm）/苯乙烯的阴离子聚合。卤素-锌交换反应，然后用炔丙基溴进行亲电捕集，提供了一条通向官能化苯丙烯的便捷途径，特别是那些具有亲电官能团（如氰基，酰胺和卤素）的苯丙二烯。气相和液相结构的光谱和计算研究表明，该二价阴离子型锌酸盐通过其庞大的配体具有非凡的稳定性。
• Photoinduced catalyst-free deborylation–deuteration of arylboronic acids with D₂O
  作者：Yatao Lang、Xiangjun Peng、Chao-Jun Li、Huiying Zeng

  DOI：10.1039/d0gc01649g

  日期：——

  deborylation–deuteration of arylboronic acids with D2O is reported. The protocol was compatible with a variety of functionalities, including halogen, alkoxy, cyano, sulfonyl, trimethylsilyl, trifluoromethoxy, alkyl, hydroxyl, free acid, amide, and heteroaromatic rings. A wide range of deuterated products were obtained in good yields with a high level of deuteration. This method provides a green and practical

  在本文中，报道了用D 2 O进行的新型光诱导的无催化剂脱芳基化-芳基硼酸氘化反应。该方案与多种功能兼容，包括卤素，烷氧基，氰基，磺酰基，三甲基甲硅烷基，三氟甲氧基，烷基，羟基，游离酸，酰胺和杂芳族环。以高收率和高收率获得了多种氘代产品。该方法为在温和条件下合成氘标记的化合物提供了绿色实用的途径。
• Mechanism of aromatic hydroxylation in the Fenton and related reactions. One-electron oxidation and the NIH shift
  作者：Tsunehiko. Kurata、Yasumasa. Watanabe、Makoto. Katoh、Yasuhiko. Sawaki

  DOI：10.1021/ja00230a032

  日期：1988.10

  Hydroxylation de benzenes substitues par le reactif de Fenton et oxydations par le peroxodisulfate

  苯的羟基化取代反应的芬顿和过氧化二硫酸盐的氧化
• Water Compatible Hypophosphites-<i>d</i>₂ Reagents: Deuteration Reaction via Deutero-deiodination in Aqueous Solution
  作者：Zejin Song、Jing Zeng、Ting Li、Xiang Zhao、Jing Fang、Lingkui Meng、Qian Wan

  DOI：10.1021/acs.orglett.0c00001

  日期：2020.3.6

  conventional deuteration approaches which typically entail deuterated solvents and/or moisture exclusion, an unprecedented deutero-deiodination reaction attainable in aqueous (H2O) solution is presented herein. By utilizing the stability of inorganic deuterated calcium/sodium hypophosphites against wayward H/D isotopic exchange within pH 2.5-11.7, these shelf-stable, nontoxic, cost-effective, and environmentally

  与通常需要氘代溶剂和/或排除水分的常规氘代方法相反，本文提出了在水溶液（H 2 O）中可获得的前所未有的氘代-碘化反应。通过利用无机氘化次磷酸钙/次磷酸钠的稳定性在pH 2.5-11.7范围内对抗随意的H / D同位素交换，这些耐贮存，无毒，经济高效且对环境有益的氘化试剂可介导各种烷基碘和芳基碘的氘代在水（H2O）溶液中加入足够的同位素。