1-acetoxy-1-phenyl-2-phenylthioethane | 16162-49-5

• 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-acetoxy-1-phenyl-2-phenylthioethane
• 英文别名: 1-phenyl-2-(phenylthio)ethyl acetate；1-Acetoxy-1-phenyl-2-(phenylthio)-ethan；(1-Phenyl-2-phenylsulfanylethyl) acetate
• CAS: 16162-49-5
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: VOMPWOVNVXDARN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetoxy-1-phenyl-2-phenylthioethane 在 水 作用下， 生成 1-phenyl-2-phenylsulfanyl-ethanol
  参考文献：
  名称：

  通过 1,2-不对称诱导从 α-氯代硫化物高度立体选择性地制备手性 α-取代的硫化物

  摘要：

  由于邻近的 CO 立体中心，通过 1,2-不对称诱导产生了具有有效立体控制的 CS 立体中心。炔丙基、烯丙基和烷基硫化物很容易以良好的收率和立体选择性从 α-氯硫化物制备。烯丙基硫化物已转化为相应的亚砜/硫亚胺/硫酰化物并进行 [2,3]-σ 重排。在该反应中观察到的有效 1,3-手性转移最终导致净 1,4-手性转移。

  DOI：

  10.1055/s-0030-1258106
• 作为产物：
  描述：

  phenylsulfenyl trifluoroacetate 在 碳酸氢钠 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 生成 1-acetoxy-1-phenyl-2-phenylthioethane
  参考文献：
  名称：

  Novel ipso-Substitution of p-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of p-Quinones and Protected p-Dihydroquinones

  摘要：

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.

  DOI：

  10.1021/jo970418o

文献信息

• Three-component difunctionalization of alkenes leading to β-acetamido sulfides and β-acetoxy sulfides
  作者：Dingyi Wang、Zhaohua Yan、Qihuang Xie、Rongxing Zhang、Sen Lin、Yuanxing Wang

  DOI：10.1039/c7ob00110j

  日期：——

  novel method for the synthesis of β-acetamido sulfides via NBS-mediated aminosulfenylation of alkenes with thiophenols and nitriles under metal-free conditions has been described. And β-acetamido sulfides were also synthesized with 1-(arylthio)pyrrolidine-2,5-diones as substrates and HBr as an additive. On the other hand, iodine-catalyzed 1,2-acetoxysulfenylation of alkenes by using (diacetoxyiodo)benzene

  已经描述了一种在无金属条件下通过NBS介导的烯烃与硫酚和腈的氨基氨基磺酰化合成β-乙酰氨基硫化物的新方法。并以1-（芳硫基）吡咯烷-2,5-二酮为底物，HBr为添加剂合成了β-乙酰氨基硫化物。另一方面，还描述了通过使用（二乙酰氧基碘）苯作为氧源来碘催化烯烃的1，2-乙酰氧基磺化，以合成各种β-乙酰氧基硫化物。
• Pummerer-type rearrangement on aromatic rings: an unprecedented ipso-substitution of the sulfinyl group of p-sulfinylphenyl ethers into oxygen functional groups leading to protected dihydroquinone derivatives
  作者：Shuji Akai、Kiyosei Iio、Yoshifumi Takeda、Hiroshi Ueno、Kayoko Yokogawa、Yasuyuki Kita

  DOI：10.1039/c39950002319

  日期：——

  The treatment of p-(phenylsulfinyl)phenyl ethers 1 with trifluoroacetic anhydride in the presence of styrene selectively caused the direct ipso-substitution of the sulfinyl groups by trifluoroacetoxy groups, giving the protected dihydroquinone derivatives 3 in high to quantitative yields.

  在苯乙烯存在下，用三氟乙酸酐处理对(苯亚磺酰基)苯基醚 1，可选择性地使亚磺酰基直接被三氟乙酰氧基取代，从而得到高产率至定量的受保护二氢醌衍生物 3。
• Reactions of Thiiranium and Sulfonium Ions with Alkenes in the Gas Phase
  作者：Samuel C. Brydon、Shea Fern Lim、George N. Khairallah、Philippe Maître、Estelle Loire、Gabriel da Silva、Richard A. J. O’Hair、Jonathan M. White

  DOI：10.1021/acs.joc.9b01264

  日期：2019.8.16

  Ion–molecule reactions between thiiranium ion 11 (m/z 213) and cyclohexene and cis-cyclooctene resulted in the formation of addition products 17a and 17b (m/z 295 and m/z 323, respectively) via an electrophilic addition pathway. Associative π-ligand exchange involving direct transfer of the PhS+ moiety, which has been observed for analogous seleniranium ions in the gas phase, did not occur despite

  硫鎓离子11（m / z 213）与环己烯和顺式-环辛烯之间的离子分子反应导致通过亲电子加成途径形成加成产物17a和17b（分别为m / z 295和m / z 323）。涉及直接转移PhS +的缔合π-配体交换尽管先前的溶液实验表明它是有效的途径，但并未在气相中观察到类似硒离子的部分发生。在理论上以M06-2X / def2-TZVP进行的DFT计算显示，交换反应的壁垒很高，而加成途径则更为合理。Hammett图为该途径提供了进一步的支持，该图显示了反应速率随硫鎓离子衍生物的苄基位置变得更亲电而增加（ρ= +1.69；R 2 = 0.974）。反应性更高的异构sulf离子22由于对红外光谱法和DFT计算观察到的反应性负责，因此被认为是异构化的可能性很小。为了进一步探索反应性的差异，分别形成了ira离子25和sulf离子27，后者的离子向顺式-环辛烯的反应速率比通过计算合理化的ira离子更
• Copper-Catalyzed 1,2-Hydroxysulfenylation of Alkene Using Disulfide via Cleavage of the S−S Bond
  作者：Nobukazu Taniguchi

  DOI：10.1021/jo060834l

  日期：2006.9.1

  Copper-catalyzed 1,2-hydroxysulfenylation of alkenes can be carried out by the use of disulfides and acetic acid in air. This reaction regio- and anti-selectively gave the corresponding 1,2-acetoxysulfides. Furthermore, the present method enables the use of both organosulfide groups of disulfide.
• Bodrikov, I. V.; Chumakov, L. V.; Pryadilova, A. N., Doklady Chemistry, 1980, vol. 251, p. 187 - 190
  作者：Bodrikov, I. V.、Chumakov, L. V.、Pryadilova, A. N.、Zefirov, N. S.、Smit, V. A.

  DOI：——

  日期：——