4-(benzyloxy)tetrahydro-2H-thiopyran | 165061-39-2

• 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: 4-(benzyloxy)tetrahydro-2H-thiopyran
• 英文别名: 4-Phenylmethoxythiane；4-phenylmethoxythiane
• CAS: 165061-39-2
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: SLKCXFBGAWQDSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)tetrahydro-2H-thiopyran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-Benzyloxy-tetrahydro-thiopyran 1,1-dioxide
  参考文献：
  名称：

  Conformational Preference in Benzyloxy- and Siloxy-substituted Thianes, Thiane 1-Oxides, and Thiane 1,1-Dioxides

  摘要：

  Conformer ratios in 4-benzyloxy- and 4-siloxy-substituted thianes, cis- and trans-thiane 1-oxides, thiane 1,1-dioxides, and dihydrothiines were revealed on the basis of their low temperature H-1 nmr analyses. Extreme benzyloxy- and siloxy-axial (or -pseudoaxial) conformer preferences in trans- thiane 1-oxides, thiane 1,1-dioxides, and dihydrothiines were clearly demonstrated.

  DOI：

  10.3987/com-94-6988
• 作为产物：
  描述：

  thian-4-yl benzoate 在 硼烷铵络合物 、 四氯化钛 作用下， 以 乙醚 为溶剂， 以97 %的产率得到4-(benzyloxy)tetrahydro-2H-thiopyran
  参考文献：
  名称：

  用硼烷-氨将酯脱氧还原为醚或醇，取决于催化剂和化学计量

  摘要：

  通过调节还原剂 BH 3 –NH 3和催化剂 TiCl 4的化学计量，实现了芳香族和脂肪族羧酸酯在室温下轻松且选择性地脱氧为醚。这是第一个实用的硼烷介导的过程，与各种潜在敏感的官能团相容，并且适用于从通常具有挑战性的芳香酸酯中形成脱氧醚。替代BF 3 –Et 2 O作为催化剂改变反应途径，将酯还原为醇。核磁共振波谱、氘标记和动力学同位素研究提供了机理见解。

  DOI：

  10.1021/acs.orglett.3c02643

文献信息

• Difluorocarbene‐Induced Ring‐Opening Difluoromethylation‐Halogenation of Cyclic (Thio)Ethers with TMSCF ₂ X (X=Br, Cl)**
  作者：Rongyi Zhang、Qigang Li、Qiqiang Xie、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/chem.202103428

  日期：2021.12.20

  protonation of difluromethylene oxonium or sulfonium ylides (generated from diflurorocarbene and cyclic (thio)ethers) constitutes the formal activation of C−O/S bond of (thio)ethers with difluormethyl cation, thus facilitating the ring-opening difluoromethylation-halogenation of cyclic (thio)ethers. (TMS=trimethylsilyl).

  二氟亚甲基氧鎓或锍叶立德（由二氟卡宾和环（硫）醚生成）的原位质子化构成（硫）醚的 C-O/S 键与二氟甲基阳离子的正式活化，从而促进开环二氟甲基化-卤化环（硫）醚。(TMS=三甲基甲硅烷基)。
• Desulfurilative self-coupling reaction of 1,3-thiazolidine-2-thiones and intramolecular non-bonded S⋯S interaction in the crystallographic structure of the products
  作者：Yoshimitsu Nagao、Hiroaki Nishijima、Hitoshi Iimori、Hideki Ushirogochi、Shigeki Sano、Motoo Shiro

  DOI：10.1016/s0022-328x(00)00460-5

  日期：2000.10

  An attempt at an asymmetric Pummerer-type reaction of trans-4-benzyloxythiane-1-oxide (1) with 3-trifluoroacetyl-4S-isopropyl-1,3-thiazolidine-2-thione (2) resulted in failure but an attractive desulfurilative self-coupling reaction of 4S-isopropyl-1,3-thiazolidine-2-thione (6) occurred to give 4S-isopropyl-3-(4S-isopropyl-1,3-thiazolin-2-yl)-1,3-thiazolidine-2-thione (5). The same desulfurilative self-coupling reaction of compound 6 or 11 efficiently proceeded by treatment of diphenyl sulfoxide (7a) or methyl phenyl sulfoxide (7b) with 2 or 3-trifluoroacetyl-1,3-thiazolidine-2-thione (8) to afford each corresponding product 5 or 9. Eventually, we found a practically useful method for the synthesis of 5 and 9 by exploiting TiCl4 and sodium salt 12 or 13 of 1,3-thiazolidine-2-thiones. Interestingly, intramolecular non-bonded S ... S interactions were recognized in the crystallographic structures of 5 and 9. (C) 2000 Elsevier Science S.A. All rights reserved.