methyl naphthalene-1-sulfinate | 137280-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl naphthalene-1-sulfinate
• 英文别名: Naphthalene-1-sulfinic acid methyl ester
• CAS: 137280-45-6
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: XXOBQEISYALAEY-UHFFFAOYSA-N

物化性质

• 沸点：
  372.6±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl naphthalene-1-sulfinate 在 potassium permanganate 、 硫酸 、 苯 作用下， 生成 methyl naphthalene-1-sulfonate
  参考文献：
  名称：

  Otto; Roessing, Journal fur praktische Chemie (Leipzig 1954), 1893, vol. <2>47, p. 165

  摘要：

  DOI：
• 作为产物：
  描述：

  萘-1-亚磺酸 生成 methyl naphthalene-1-sulfinate
  参考文献：
  名称：

  283.萘磺酸的化合物及其钠盐和钾盐

  摘要：

  DOI：

  10.1039/jr9380001490

文献信息

• NaHSO ₃ ‐Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition‐Metal‐Free Conditions
  作者：Guofu Zhang、Qiankun Fan、Huimin Wang、Yiyong Zhao、Chengrong Ding

  DOI：10.1002/adsc.202001202

  日期：2021.2.2

  We have developed a protocol for the NaHSO3‐promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition‐metal‐free reaction conditions, an inexpensive and available reagent, and operational simplicity.

  我们已经开发了一种用于NaHSO 3促进的磺酰肼与醇酯化反应的方案，用于合成亚磺酸酯。各种磺酰基酰肼可以良好或高收率地转化为相应的亚磺酸酯。该方案的优点包括温和的无过渡金属反应条件，廉价且可用的试剂以及操作简便性。对照实验表明，这种转化可能是通过自由基途径进行的。
• Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates
  作者：Bingnan Du、Zan Li、Ping Qian、Jianlin Han、Yi Pan

  DOI：10.1002/asia.201501262

  日期：2016.2

  A Cu‐catalyzed aerobic oxidative reaction between sulfonyl hydrazides and alcohols has been developed. In this reaction, sulfonyl hydrazides act as the sulfinic acid precursors to react with alcohols, resulting in sulfinic esters with up to 72 % yield. This catalytic system tolerates a wide range of sulfonyl hydrazide substrates, and represents a new strategy for the transformation of readily available

  已开发出磺酰肼与醇之间的Cu催化的好氧氧化反应。在该反应中，磺酰肼充当亚磺酸前体与醇反应，从而以高达72％的收率生成亚磺酸酯。该催化体系可耐受各种磺酰肼底物，并代表了一种易于转化的磺酰肼转化的新策略。
• NMR of terminal oxygen. 6—17O NMR of the SO ‘double bond’: Derivatives of arylsulphinic and arylsulphonic acids
  作者：Hans Dahn、Vien Van Toan、My-Ngoc Ung-Truong

  DOI：10.1002/mrc.1260290907

  日期：1991.9

  oxygen atoms in esters, anions and amides of substituted arenesulphinic acids and in esters and amides of substituted arenesulphonic acids were measured. The signals of the terminal O appear close to those of the bridge O. Compared with carbonyl O, terminal SO shows (a) a lower sensitivity to the electronic influences of geminal groups, (b) only a low sensitivity to arene ring substituents and (c) small

  测量了取代芳烃磺酸的酯、阴离子和酰胺以及取代芳烃磺酸的酯和酰胺中末端氧原子的 17O NMR 谱。末端 O 的信号看起来接近桥 O 的信号。 与羰基 O 相比，末端 SO 显示 (a) 对孪晶基团的电子影响的敏感性较低，(b) 对芳烃环取代基的敏感性较低(c) 小的溶剂效应。根据 π 键特性讨论 C 键和 S 键 O 之间的差异。Dy3+ 与甲基芳烃亚磺酸盐中的 O 端发生络合。
• Metal- and oxidant-free electrochemical synthesis of sulfinic esters from thiols and alcohols
  作者：Chongren Ai、Haiwei Shen、Dingguo Song、Yujin Li、Xiao Yi、Ze Wang、Fei Ling、Weihui Zhong

  DOI：10.1039/c9gc02125f

  日期：——

  An efficient and eco-friendly electrochemical synthesis of various sulfinic esters from thiols and alcohols via sequential S–H/S bond cleavage and double S–O bond formation under mild reaction conditions has been developed. Stoichiometric oxidants, metal catalysts, activating agents and even added bases were avoided in this method, and the only by-product generated from this reaction was dihydrogen

  已经开发了在温和的反应条件下，通过顺序的S-H / S键断裂和双S-O键形成，从硫醇和醇中高效合成环保的亚磺酸酯的电化学方法。该方法避免了化学计量的氧化剂，金属催化剂，活化剂甚至添加的碱，该反应产生的唯一副产物是可作为绿色能源的二氢气体。各种功能组都与此绿色协议兼容，可以轻松地以克为单位进行操作。
• Electrochemical synthesis of sulfinic and sulfonic esters from sulfonyl hydrazides
  作者：Suji Kim、Sunwoo Lee

  DOI：10.1039/d4ob00215f

  日期：——

  synthesis of sulfinic esters and sulfonic esters from sulfonyl hydrazides was developed. Alkyl sulfinic esters were synthesized by treating sulfonyl hydrazides with trialkyl orthoformate in a DMF solvent at a constant current of 5 mA and then optimizing the reaction conditions. Conversely, alkyl sulfonic esters were exclusively obtained when the reaction was conducted in alkyl alcohol solvents at a constant

  开发了一种由磺酰肼合成亚磺酸酯和磺酸酯的电化学合成方法。在DMF溶剂中，5 mA恒电流下，用原甲酸三烷基酯处理磺酰肼，然后优化反应条件，合成烷基亚磺酸酯。相反，当反应在烷基醇溶剂中以15mA的恒定电流进行时，仅获得烷基磺酸酯。各种取代的芳基磺酰肼提供了中等至良好产率的所需亚磺酸酯和磺酸酯。机理研究表明，磺酰基自由基是通过电化学氧化形成的，并且它们与烷基自由基或烷氧基自由基反应生成各自的酯产物。