2,2-Bis(phenylsulfanyl)acetyl chloride | 98834-76-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,2-Bis(phenylsulfanyl)acetyl chloride
• CAS: 98834-76-5
• 化学式: C₁₄H₁₁ClOS₂
• 分子量: 294.826
• InChiKey: LHVDVFKFWLOJCO-UHFFFAOYSA-N

物化性质

• 沸点：
  387.2±32.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Bis(phenylsulfanyl)acetyl chloride 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲苯 、 苯 为溶剂， 反应 2.5h， 生成 2-phenylthio-N-[o-(prop-2-enyl)phenyl]-N-(p-toluenesulfonyl)acetamide
  参考文献：
  名称：

  Synthesis of Tetrahydro-1-benzazocin-2(1H)-ones Using 8-endo-trig Radical Cyclization of 2,2-Bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides

  摘要：

  The effects of N-substituents upon the 8-endo-trig radical cyclization of 2,2-bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides (4) were examined. The N-(p-methoxybenzyl) (4a) and N-tosyl derivatives (4b), when treated with tributyltin hydride in the presence of a small amount of azoisobutyronitrile, gave regioselectively the corresponding 3,4,5,6-tetrahydro-3-phenylthio-1-benzazocin-2(1H)-ones (5a,b) (8-endo cyclization products) in 40 and 47% yields, respectively, while the N-unsubstituted derivative (4c) afforded the reduction products (6c) and (8) as the major products, Some chemical transformation reactions of 5a are also described.

  DOI：

  10.3987/com-96-s8
• 作为产物：
  描述：

  Ethyl bis(phenylthio)-acetate 在 氯化亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 2,2-Bis(phenylsulfanyl)acetyl chloride
  参考文献：
  名称：

  Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts

  摘要：

  含有α位电子吸引酯、乙酰、酰胺和腈基团的二硫代缩醛的阳极氟化反应进行了比较研究，使用了各种支持性聚合物(HF)盐，如Et₃N·nHF (n = 3–5)和Et₄NF·nHF (n = 3–5)。在前两种情况下，根据使用的支持性聚合物(HF)盐，选择性地获得了相应的α-氟化产物或氟去硫化产物。与此形成鲜明对比的是，在后两种情况下，氟化产物的选择性受到α位取代基的电子吸引能力的强烈影响：含有相对较弱的电子吸引酰胺基团的二硫代缩醛选择性地提供氟去硫化产物，而具有强烈电子吸引腈基团的二硫代缩醛无论使用何种聚合物(HF)盐，主要产生α-氟化产物。

  DOI：

  10.3762/bjoc.11.12

文献信息

• Functionalized Heterocumulenes: Synthesis and Applications of Phenylthiomethyl, Methylthiomethyl, Bis[phenylthio]methyl Isocyanates and Phenylthio-acetyl and Methylthio-acetyl Isothiocyanates
  作者：Yoshiki Ohshiro、Naotami Ando、Mitsuo Komatsu、Toshio Agawa

  DOI：10.1055/s-1985-31175

  日期：——
• sato, Tatsunori; Chono, Noriko; Ishibashi, Hiroyuki, Journal of the Chemical Society. Perkin transactions I, 1995, # 9, p. 1115 - 1120
  作者：sato, Tatsunori、Chono, Noriko、Ishibashi, Hiroyuki、Ikeda, Masazumi

  DOI：——

  日期：——
• 5-endo-trig Radical Cyclization of 2-Chloro- and 2,2-Bis(phenylthio)-N-methyl- N-(6-phenylcyclohex-1-en-1-yl)-acetamides
  作者：Masazumi Ikeda、Shinji Ohtani、Michiyo Okada、Emi Minakuchi、Tatsunori Sato、Hiroyuki Ishibashi

  DOI：10.3987/com-96-7629

  日期：——

  Treatment of 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)-acetamide (4a) with Bu3SnH in the presence of AIBN gave a 2.5:1 mixture of cis- and trans-fused N-methyl-7-phenyloctahydroindol-2-ones (5a and 5b) (13% combined yield), N-methyl-N-(2-phenylcyclohex-1-en-1-yl)acetamide (6) (19%), N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide (7) (13%), and N-(cyclohex-1-en-1-yl) -N-methyl-2-phenylacetamide (8) (4%). Similar treatment of the 2,2-bis(phenylthio)acetamide (4b) gave a 1:1 mixture of 5a and 5b (61% combined yield) along with 6 (24%) and 7 (trace). Possible mechanisms for the formation of the products (6)-(8) are also discussed.
• OHSHIRO, YOSHIKI;ANDO, NAOTAMI;KOMATSU, MITSUO;AGAWA, TOSHIO, SYNTHESIS, BRD, 1985, N 5, 276-279
  作者：OHSHIRO, YOSHIKI、ANDO, NAOTAMI、KOMATSU, MITSUO、AGAWA, TOSHIO

  DOI：——

  日期：——
• Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts
  作者：Bin Yin、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.3762/bjoc.11.12

  日期：——

  Anodic fluorination of dithioacetals bearing electron-withdrawing ester, acetyl, amide, and nitrile groups at their α-positions was comparatively studied using various supporting poly(HF) salts like Et₃N·nHF (n = 3–5) and Et₄NF·nHF (n = 3–5). In the former two cases, the corresponding α-fluorination products or fluorodesulfurization products were obtained selectively depending on supporting poly(HF) salts used. In sharp contrast, in the latter two cases, fluorination product selectivity was strongly affected by the electron-withdrawing ability of α-substituents: A dithioacetal bearing a relatively weak electron-withdrawing amide group provided a fluorodesulfurization product selectively while a dithioacetal having a strongly electron-withdrawing nitrile group gave the α-fluorination product predominantly regardless of the poly(HF) salts used.

  含有α位电子吸引酯、乙酰、酰胺和腈基团的二硫代缩醛的阳极氟化反应进行了比较研究，使用了各种支持性聚合物(HF)盐，如Et₃N·nHF (n = 3–5)和Et₄NF·nHF (n = 3–5)。在前两种情况下，根据使用的支持性聚合物(HF)盐，选择性地获得了相应的α-氟化产物或氟去硫化产物。与此形成鲜明对比的是，在后两种情况下，氟化产物的选择性受到α位取代基的电子吸引能力的强烈影响：含有相对较弱的电子吸引酰胺基团的二硫代缩醛选择性地提供氟去硫化产物，而具有强烈电子吸引腈基团的二硫代缩醛无论使用何种聚合物(HF)盐，主要产生α-氟化产物。