3-(对甲苯磺酰基)丁酸 | 104398-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(对甲苯磺酰基)丁酸
• 中文别名: 丁酸,3-[(4-甲基苯基)磺酰]-
• 英文名称: 3-tosylbutanoic acid
• 英文别名: 3-(4-Methylphenyl)sulfonylbutanoic acid
• CAS: 104398-01-8
• 化学式: C₁₁H₁₄O₄S
• 分子量: 242.296
• InChiKey: BWKPKKWDCXHCNV-UHFFFAOYSA-N

物化性质

• 沸点：
  456.7±45.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(对甲苯磺酰基)丁酸 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids

  摘要：

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

  DOI：

  10.1021/jo00090a043
• 作为产物：
  描述：

  3-(4-methylphenylthio)butanoic acid 在 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 3-(对甲苯磺酰基)丁酸
  参考文献：
  名称：

  A structure–taste study of arylsulfonyl(cyclo)alkanecarboxylic acids

  摘要：

  A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds 14 containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.056

文献信息

• Lithium 3-lithio-3-tosylpropanoate: A useful α-tosylated homoenolate anion
  作者：Pedro Bonete、Carmen Nájera

  DOI：10.1016/0040-4039(92)88101-a

  日期：1992.7

  Lithium 3-lithio-3-tosylpropanoate (7), prepared by dilithiation of 3-tosylpropanoic acid (6) with n-butyllithium at −78°C, reacts with different elctrophiles yielding the expected 3-functionalized tosylated propanoic acids 8. When carbonyl compounds are used as electrophiles the corresponding α,β-butenolides are prepared directly.

  通过在-78°C下将3-甲苯基丙酸（6）与正丁基锂二锂化制备的3-lithio-3-甲苯基丙酸锂（7）与不同的亲电子试剂反应生成预期的3-官能化甲苯磺酸丙酸8。当羰基化合物用作亲电试剂时，可以直接制备相应的α，β-丁烯内酯。
• Water‐Promoted Michael Addition Reaction of Sulfonyl Hydrazides and α, β‐Unsaturated Propionic Acids to 3‐Sulfone Propionic Acids
  作者：Zhiyuan Qi、Yifan Liu、Qilong Zhang、Panfeng Zhao、Lingfeng Gao、Xu Sun、Gengxiu Zheng

  DOI：10.1002/ejoc.202101456

  日期：2022.4.27

  sulfohydrazine with α,β unsaturated propionic acid to obtain 3-sulfopropionic acid compound with high yield. The reaction can proceed smoothly under environmentally friendly conditions and all catalysts, ligands or organic solvents can be completely replaced by water. The reaction crystallization and purification process is simple, efficient and easy to get 3-sulfoxide propionic acid.

  水促进磺酰肼与α,β不饱和丙酸发生迈克尔加成反应，得到高收率的3-磺基丙酸化合物。该反应可以在环保条件下顺利进行，所有催化剂、配体或有机溶剂均可完全被水替代。该反应结晶纯化工艺简单、高效、易得3-亚砜丙酸。
• 924. The decomposition of toluene-p-sulphonylhydrazones by alkali
  作者：W. R. Bamford、T. S. Stevens

  DOI：10.1039/jr9520004735

  日期：——
• Achmatowicz; Michalski, Roczniki Chemii, 1956, vol. 30, p. 243,Tab.2 nach S.246,250
  作者：Achmatowicz、Michalski

  DOI：——

  日期：——
• A Bi(OTf)₃-Promoted Hydrosulfonylation of Alkenes with Sulfonyl Hydrazides: An Approach to Branched Sulfones
  作者：Zheng Zhou、Qianqian Liu、Zhibin Huang、Yingsheng Zhao

  DOI：10.1021/acs.orglett.2c01657

  日期：2022.6.24