1,1-bis(phenylthio)-2-heptyne | 114245-26-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,1-bis(phenylthio)-2-heptyne
• 英文别名: 2-heptynyl-1,1-bis thiobenzene；1-Phenylsulfanylhept-2-ynylsulfanylbenzene
• CAS: 114245-26-0
• 化学式: C₁₉H₂₀S₂
• 分子量: 312.5
• InChiKey: JHIGWYWVDDBGJB-UHFFFAOYSA-N

物化性质

• 沸点：
  434.1±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-bis(phenylthio)-2-heptyne 在 盐酸 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 3-chloro-1-heptenyl-1,1-bis thiobenzene
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic Phenyl Sulfides.

  摘要：

  2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu-II salts, gave alpha,beta-unsaturated aldehydes.2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to alpha,beta-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.

  DOI：

  10.1080/00397919708005915
• 作为产物：
  描述：

  苯硫酚 、 1-Chlorohept-2-ynylsulfanylbenzene 在 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 以66%的产率得到1,1-bis(phenylthio)-2-heptyne
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic Phenyl Sulfides.

  摘要：

  2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu-II salts, gave alpha,beta-unsaturated aldehydes.2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to alpha,beta-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.

  DOI：

  10.1080/00397919708005915

文献信息

• Preparation and Reaction of γ-Ethoxy and (Phenylthio)allenylstannanes
  作者：Takeshi Takeda、Hiroyuki Ohshima、Masami Inoue、Akira Togo、Tooru Fujiwara

  DOI：10.1246/cl.1987.1345

  日期：1987.7.5

  γ-Ethoxyallenylstannane was obtained by the reaction of 2-ethoxy-3-alkynenitrile or 1-ethoxy-1-(phenylthio)-2-alkyne with tributylstannyllithium in good yield. The reaction of 1,1-bis-(phenylthio)-2-alkyne with tributylstannylcopper(I) reagent gave γ-(phenylthio)allenylstannane which, in turn, was treated with acetal in the presence of TiCl4, to afford the propargyl sulfide derivative predominantly.

  γ-乙氧基乙炔基锡烷是通过2-乙氧基-3-炔腈或1-乙氧基-1-(苯硫基)-2-炔与三丁基锡锂反应得到的，产率良好。1,1-双-(苯硫基)-2-炔与三丁基锡铜(I)试剂反应生成γ-(苯硫基)乙炔基锡烷，后者在TiCl4存在下与缩醛反应，主要生成炔丙基硫醚衍生物。
• Preparation of alkynylcyclopropanes by the titanocene(II)-promoted reaction of 1,1-bis(phenylthio)-2-alkynes with 1-alkenes
  作者：Takeshi Takeda、Shuichi Kuroi、Kenjirou Yanai、Akira Tsubouchi

  DOI：10.1016/s0040-4039(02)01134-6

  日期：2002.8

  The desulfurization of 1,1-bis(phenylthio)-2-alkynes with the titanocene(II) species Cp2Ti[P(OEt)3]2 in the presence of 1-alkenes produced 1-alkyn-1-ylcyclopropanes in good yields.

  在1-烯烃存在下，用钛茂（II）物种Cp 2 Ti [P（OEt）3 ] 2对1,1-双（苯硫基）-2-炔烃进行脱硫，生成了1-炔基-1-基环丙烷产量。
• TAKEDA, TAKESHI;OHSHIMA, HIROYUKI;INOUE, MASAMI;TOGO, AKIRA;FUJIWARA, TOO+, CHEM. LETT.,(1987) N 7, 1345-1348
  作者：TAKEDA, TAKESHI、OHSHIMA, HIROYUKI、INOUE, MASAMI、TOGO, AKIRA、FUJIWARA, TOO+

  DOI：——

  日期：——
• Synthesis of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic Phenyl Sulfides.
  作者：Fortes, Carlos C.、Garrote, Clevia F. D.

  DOI：10.1080/00397919708005915

  日期：1997.11

  2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu-II salts, gave alpha,beta-unsaturated aldehydes.2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to alpha,beta-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.