1-(1-isothiocyanato-2-methylethyl)-4-methoxybenzene

• 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: 1-(1-isothiocyanato-2-methylethyl)-4-methoxybenzene
• 英文别名: 1-(1-isothiocyanatopropyl)-4-methoxybenzene；1-(1-Isothiocyanatopropyl)-4-methoxybenzene
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: YBUHLVCZIXWAFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 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：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-丙基苯酚 在 sodium hydride 、 Selectfluor 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 3.5h， 生成 1-(1-isothiocyanato-2-methylethyl)-4-methoxybenzene
  参考文献：
  名称：

  通过氢原子转移和一锅法衍生异硫氰酸酯光诱导合成硫氰酸酯

  摘要：

  描述了光诱导的苄基 C-H 硫氰化。以Selectfluor为氧化剂，高效制得了一系列硫氰酸烷基酯。此外，我们完成了 C-H 硫氰化后的一锅异硫氰化。硫氰酸盐和异硫氰酸盐被应用于药物的发散转化。

  DOI：

  10.1021/acs.orglett.2c02896

文献信息

• Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor
  作者：Emma S. Spencer、Edward J. Dale、Aimée L. Gommans、Malcolm T. Rutledge、Christine T. Vo、Yoshio Nakatani、Allan B. Gamble、Robin A.J. Smith、Sigurd M. Wilbanks、Mark B. Hampton、Joel D.A. Tyndall

  DOI：10.1016/j.ejmech.2015.02.012

  日期：2015.3

  Macrophage migration inhibitory factor (MIF) is a pleiotropic cytokine that has roles in the innate immune response, and also contributes to inflammatory disease. While the biological properties of MIF are closely linked to protein protein interactions, MW also has tautomerase activity. Inhibition of this activity interferes with the interaction of MIF with protein partners e.g. the CD74 receptor, and tautomerase inhibitors show promise in disease models including multiple sclerosis and colitis. Isothiocyanates inhibit MIF tautomerase activity via covalent modification of the N-terminal proline. We systematically explored variants of benzyl and phenethyl isothiocyanates, to define determinants of inhibition. In particular, substitution with hydroxyl, chloro, fluoro and trifluoro moieties at the para and meta positions were evaluated. In assays on treated cells and recombinant protein, the IC50 varied from 250 nM to >100 mu M. X-ray crystal structures of selected complexes revealed that two binding modes are accessed by some compounds, perhaps owing to strain in short linkers between the isothiocyanate and aromatic ring. The variety of binding modes confirms the existence of two subsites for inhibitors and establishes a platform for the development of potent inhibitors of MIF that only need to target one of these subsites. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Photoinduced Synthesis of Thiocyanates through Hydrogen Atom Transfer and One-Pot Derivatization to Isothiocyanates
  作者：Bumpei Maeda、Yusuke Aihara、Ayato Sato、Toshinori Kinoshita、Kei Murakami

  DOI：10.1021/acs.orglett.2c02896

  日期：2022.10.14

  Photoinduced benzylic C–H thiocyanation is described. A series of alkyl thiocyanates were efficiently obtained by using Selectfluor as the oxidant. Moreover, we accomplished the one-pot isothiocyanation following the C–H thiocyanation. The thiocyanates and isothiocyanates were applied to the divergent transformation of pharmaceuticals.

  描述了光诱导的苄基 C-H 硫氰化。以Selectfluor为氧化剂，高效制得了一系列硫氰酸烷基酯。此外，我们完成了 C-H 硫氰化后的一锅异硫氰化。硫氰酸盐和异硫氰酸盐被应用于药物的发散转化。