2,4-dimethoxybenzenesulfinate sodium

• 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: 2,4-dimethoxybenzenesulfinate sodium
• 英文别名: Sodium 2,4-dimethoxybenzene-1-sulfinate；sodium;2,4-dimethoxybenzenesulfinate
• 化学式: C₈H₉O₄S*Na
• 分子量: 224.213
• InChiKey: NVNPAMYRUFFLQJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.05
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxybenzenesulfinate sodium 以 溶剂黄146 为溶剂， 生成 Acetic acid (2E,6E,8E)-5-(2,4-dimethoxy-benzenesulfonyl)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienyl ester
  参考文献：
  名称：

  通过砜合成维生素A：C15砜路线。

  摘要：

  AbstractA Synthesis of vitamin A has been achieved by alkylating a β‐ionylidene‐ethyl (C15) aromatic sulfone with 1‐acetoxy‐3‐chlormethyl‐2‐butene (C5) followed by elimination of the corresponding sulfinic acid.

  DOI：

  10.1002/hlca.19760590207

文献信息

• Palladium-Catalyzed Ring-Opening Coupling of <i>gem</i>-Difluorocyclopropanes for the Construction of 2-Fluoroallylic Sulfones
  作者：Jiabin Ni、Bekzod Nishonov、Azizbek Pardaev、Ao Zhang

  DOI：10.1021/acs.joc.9b01897

  日期：2019.11.1

  A Pd-catalyzed ring-opening sulfonylation of gem-difluorocyclopropanes is reported. This protocol involves C-C bond cleavage, β-F elimination, and allylic coupling to form corresponding 2-fluoroallylic sulfones efficiently with Z-selectivity. Different substrates bearing diverse functional groups are tolerated. Moreover, this method is successfully used for the late-stage derivation of several bioactive

  报道了钯-催化的宝石-二氟环丙烷的开环磺酰化。该方案涉及CC键裂解，β-F消除和烯丙基偶联以Z选择性有效地形成相应的2-氟烯丙基砜。容许带有不同官能团的不同底物。此外，该方法已成功用于几种生物活性分子的后期衍生。
• Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications
  作者：Muhammad Salman、Yaoyao Xu、Shahid Khan、Junjie Zhang、Ajmal Khan

  DOI：10.1039/d0sc01763a

  日期：——

  The first molybdenum-catalyzed allylic sulfonylation of tertiary allylic electrophiles is described. The method employs a readily accessible catalyst (Mo(CO)6/2,2′-bipyridine, both are commercially available) and represents the first example of the use of a group 6 transition metal-catalyst for allylic sulfonylation of substituted tertiary allylic electrophiles to form carbon–sulfur bonds. This atom

  描述了第三级烯丙基亲电试剂的第一钼催化的烯丙基磺酰化。该方法采用易于获得的催化剂（Mo（CO）6 / 2,2'-联吡啶，均可商购），并且是使用第6组过渡金属催化剂进行取代的叔烯丙基亲电子试剂的烯丙基磺酰化的第一个实例。形成碳硫键。这种原子经济且操作简单的方法，其特点是相对温和的条件，较宽的底物范围和出色的区域选择性，因此即使在后期功能化的情况下，也可以开辟一个新的平台来锻造砜部分，并为进一步衍生化提供了充足的机会通过传统的铃木交叉偶联反应。
• Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF₃
  作者：Changge Zheng、Chao Jiang、Shuai Huang、Kui Zhao、Yingying Fu、Mingyu Ma、Jianquan Hong

  DOI：10.1021/acs.orglett.1c02656

  日期：2021.9.3

  Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert–Prakash reagent TMSCF3. This approach is also a potential alternative to the current industrial production method owing to facile substrates

  在此，我们报告了芳基亚磺酸钠的间接三氟甲硫基化反应。这种无过渡金属的反应显着提供了一种使用商业 Ruppert-Prakash 试剂 TMSCF 3 的芳基三氟甲基硫醚的环境友好且实用的合成方法。由于易于使用的底物、优异的官能团兼容性和操作简单，这种方法也是当前工业生产方法的潜在替代方案。
• Palladium nanoparticles as efficient catalyst for C–S bond formation reactions
  作者：Mei-Na Zhang、Shahid Khan、Junjie Zhang、Ajmal Khan

  DOI：10.1039/d0ra05848c

  日期：——

  heterogeneous palladium-catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates via decarboxylative cross-coupling. Both aliphatic and aromatic sulfinate salts react with various vinyl cyclic carbonates to deliver the desired allylic sulfones featuring tri- and even tetrasubstituted olefin scaffolds in high yields with excellent selectivity. The process needs only 2 mol% of Pd2(dba)3 and

  发展绿色、经济和可持续的化学工艺是有机合成的主要挑战之一。在此，我们报道了通过脱羧交叉偶联，乙烯基环状碳酸酯与亚磺酸钠的高效非均相钯催化磺酰化反应。脂肪族和芳香族亚磺酸盐与各种乙烯基环状碳酸酯反应，以高产率和优异的选择性提供所需的具有三取代甚至四取代的烯烃骨架的烯丙基砜。该过程仅需要2 mol%的Pd 2 (dba) 3并且发现原位形成的钯纳米颗粒是活性催化剂。
• Tungsten-Catalyzed Allylic Substitution with a Heteroatom Nucleophile: Reaction Development and Synthetic Applications
  作者：Yaoyao Xu、Muhammad Salman、Shahid Khan、Junjie Zhang、Ajmal Khan

  DOI：10.1021/acs.joc.0c01632

  日期：2020.9.4

  nucleophile was developed. The reaction utilizes inexpensive and readily available (CH3CN)3W(CO)3 as a precatalyst and proceeds at 60 °C temperature in the presence of 2,2′-bipyridine and its derivatives as ligand. The synthetic utility of allylic sulfones as electrophile was further demonstrated through Suzuki–Miyaura cross-coupling as showcased by the formal synthesis of (±)-hinokiresinol.

  开发了钨催化的亚磺酸钠作为杂原子亲核试剂的烯丙基烯丙基化。该反应利用廉价且容易获得的（CH 3 CN）3 W（CO）3作为预催化剂，并在2,2'-联吡啶及其衍生物作为配体的存在下于60°C进行。（±）-hinokiresinol的正式合成表明，通过Suzuki-Miyaura交叉偶联进一步证明了烯丙基砜作为亲电试剂的合成效用。