3-(benzhydrylthio)propanoic acid | 63547-34-2

• 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: 3-(benzhydrylthio)propanoic acid
• 英文别名: Propanoic acid, 3-[(diphenylmethyl)thio]-；3-benzhydrylsulfanylpropanoic acid
• CAS: 63547-34-2
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: UPGWRBLQPLHELY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(benzhydrylthio)propanoic acid 在 草酰氯 、 氨 作用下， 以 二氯甲烷 为溶剂， 生成 3-(benzhydrylthio)propanamide
  参考文献：
  名称：

  Nitridoosmium(VI) and nitridoruthenium(VI) complexes of cysteine(2-) and related ligands

  摘要：

  Anionic complexes of nitridoruthenium(VI) and nitridoosmium(VI) containing covalently bound N-acetyl-L-cysteinato, 3-sulfidopropionato, and 3-sulfidopropionamidato ligands have been synthesized to model the binding of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine to the iron center in the metalloenzyme isopenicillin N synthetase. The complexes are prepared by the reaction of N-acetyl-L-cysteine, 3-mercaptopropionic acid, and 3-mercaptopropionamide with [NBu(n)4][Os(N)(OSiMe3)4], [NBu(n)4][Os(N)Cl4], [NBu(n)4][Ru(N)(CH2SiMe3)4], or [NBu(n)4][Ru(N)(OSiMe3)4]. They have been characterized by elemental analysis and IR and NMR spectroscopy. Spectroscopic data show that the N-acetyl-L-cysteinato and 3-sulfidopropionato ligands are bound to the metal center through sulfur and oxygen, while the 3-sulfidopropionamidato ligands are bound through sulfur and nitrogen. The molecular structures of cis-[NBu(n)4][Os(N)(O2CCH2CH2S)2], [NBu(n)4][Os(N){O2CCH(NHCOCH3)CH2S}2], and [PPh4][Ru(N)(NHCOCH2CH2S)2)] were determined by single-crystal X-ray diffraction. These complexes were found to have distorted square-pyramidal geometry around the metal center. cis-[NBu(n)4][Os(N)(O2CCH2CH2S)2] crystallizes in monoclinic space group P2(1)/c with a = 13.718 (6) angstrom, b = 10.080 (3) angstrom, c = 19.890 (5) angstrom, beta = 92.16 (3) angstrom, and Z = 4. [NBu(n)4][Os(N){L-O2CCH(NHCOCH3)CH2S}2] crystallizes in monoclinic space group C2 with a = 18.371 (6) angstrom, b = 9.261 (1) angstrom, c = 21.125 (7) angstrom, beta = 102.92 (3) angstrom, and Z = 4. [PPh4][Ru(N)(NHCOCH2CH2S)2)] crystallizes in orthorhombic space group Pbca with a = 23.022 (1) angstrom, b = 16.120 (1) angstrom, c = 15.728 (1) angstrom, and Z = 8.

  DOI：

  10.1021/ja00016a031
• 作为产物：
  描述：

  β--propionsaeure 在 sodium hydroxide 作用下， 生成 3-(benzhydrylthio)propanoic acid
  参考文献：
  名称：

  Schoenberg; Iskander, Journal of the Chemical Society, 1942, p. 90,92

  摘要：

  DOI：

文献信息

• Cationic palladium(<scp>ii</scp>)-catalyzed dehydrative nucleophilic substitutions of benzhydryl alcohols with electron-deficient benzenethiols in water
  作者：Hidemasa Hikawa、Yumo Machino、Mariko Toyomoto、Shoko Kikkawa、Isao Azumaya

  DOI：10.1039/c6ob01140c

  日期：——

  An efficient direct nucleophilic substitution of benzhydryl alcohols with electron-deficient benzenethiols using cationic Pd(II) catalysts as Lewis acids in water is reported. Atom economical and environmentally benign protocols afford S-benzylated products in moderate to excellent yields. Commercially available Pd(MeCN)4(OTf)2, PdCl2(MeCN)2, and Na2PdCl4 are highly efficient catalysts. Notably, this

  报道了使用阳离子Pd（II）催化剂作为路易斯酸在水中用缺电子的苯硫醇对苯二酚进行有效的直接亲核取代。原子经济和环保的协议可提供中等至极好的收率的S-苄基化产物。市售的Pd（MeCN）4（OTf）2，PdCl 2（MeCN）2和Na 2 PdCl 4是高效催化剂。值得注意的是，无需任何其他添加剂（例如酸，碱或外部配体）就可以实现此简单方案。Hammett研究S的速率常数通过使用各种取代的苄醇进行的苄基化反应产生负ρ值，这表明在过渡态中会积聚正电荷。
• 454. The carbon–sulphur fission in thio-ethers. Part I. The retarding influence of α-methyl groups and of the length of the acid chain on the alkaline hydrolysis of (2-ketoalkylthio)- and (p-nitrotriphenylmethylthio)-acetic acids
  作者：Youssef Iskander、Rasmy Tewfik

  DOI：10.1039/jr9510002050

  日期：——
• US4098824A
  申请人：——

  公开号：US4098824A

  公开（公告）日：1978-07-04
• US4127722A
  申请人：——

  公开号：US4127722A

  公开（公告）日：1978-11-28
• Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides
  作者：Susannah E. Huth、Nicolò Tampellini、Maria D. Guerrero、Scott J. Miller

  DOI：10.1021/acs.orglett.4c02452

  日期：2024.8.16