1-Phenylthio-1-dodecyne | 130612-90-7

• 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-Phenylthio-1-dodecyne
• 英文别名: dodec-1-yn-1-yl(phenyl)sulfane；Dodec-1-ynylsulfanylbenzene
• CAS: 130612-90-7
• 化学式: C₁₈H₂₆S
• 分子量: 274.47
• InChiKey: KCGFDSVLXXQION-UHFFFAOYSA-N

物化性质

• 沸点：
  382.7±25.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  苯基锂 、 1-Phenylthio-1-dodecyne 在 selenium 、 水 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 4.0h， 以64%的产率得到(Z)-1-phenylthio-2-phenylseleno-1-dodecene
  参考文献：
  名称：

  One-pot synthesis of mixed ( )-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel β-organylthio vinyllithium intermediates

  摘要：

  One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.112
• 作为产物：
  描述：

  1-十二炔 、 二苯二硫醚 在 铜 、 氧气 、 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 70.0 ℃ 、202.66 kPa 条件下， 反应 12.0h， 以61%的产率得到1-Phenylthio-1-dodecyne
  参考文献：
  名称：

  铜纳米粒子通过S–S和C–H键的活化催化C–S键的形成：炔烃硫化物的简便方法

  摘要：

  摘要 通过使用二甲基亚砜作为溶剂，碱和分子氧作为绿色氧化剂，开发了一种有效的铜纳米颗粒催化无配体SC键形成的方法。这项研究为通过S–S和C–H键的双重活化生产炔基硫化物提供了一条新的催化途径。以低催化剂负载量（0.5mol％Cu）大规模合成了各种各样的炔基硫化物。这种合成方法也可以扩展到硒化物，而碲化物在没有催化剂的情况下进行类似的反应。 通过使用二甲基亚砜作为溶剂，碱和分子氧作为绿色氧化剂，开发了一种有效的铜纳米颗粒催化无配体SC键形成的方法。这项研究为通过S–S和C–H键的双重活化生产炔基硫化物提供了一条新的催化途径。以低催化剂负载量（0.5mol％Cu）大规模合成了各种各样的炔基硫化物。这种合成方法也可以扩展到硒化物，而碲化物在没有催化剂的情况下进行类似的反应。

  DOI：

  10.1055/s-0035-1560458

文献信息

• Cu(i)-catalyzed aerobic cross-dehydrogenative coupling of terminal alkynes with thiols for the construction of alkynyl sulfides
  作者：Yong Yang、Weibing Dong、Yisong Guo、Robert M. Rioux

  DOI：10.1039/c3gc41330f

  日期：——

  and selective aerobic cross-dehydrogenative coupling of terminal alkynes with thiols to construct alkynyl sulfides catalyzed by Cu(I) using molecular oxygen as the oxidant has been demonstrated under mild reaction conditions. The process is applicable to a wide range of alkynes and various thiols and is compatible with a variety of functional groups on both alkyne and thiol coupling partners.

  已证明在温和的反应条件下，末端炔烃与硫醇的高活性和选择性好氧交叉脱氢偶联，以使用分子氧作为氧化剂由Cu（I）催化构建炔基硫化物。该方法适用于各种炔烃和各种硫醇，并且与炔烃和硫醇偶合伙伴上的各种官能团均相容。
• Regioselectivity in the reaction of tantalum-unsymmetrical acetylene complexes with carbonyl compounds. Stereoselective preparation of 1-alkenyl sulfides, .alpha.,.beta.-unsaturated esters, and amides
  作者：Yasutaka Kataoka、Jiro Miyai、Makoto Tezuka、Kazuhiko Takai、Kiitiro Utimoto

  DOI：10.1021/jo00051a023

  日期：1992.12

  Tantalum-alkyne complexes, derived by treatment of alkynes with low-valent tantalum (TaCl5 and zinc), react in situ with carbonyl compounds to give (E)-allylic alcohols stereoselectively. When unsymmetrical acetylenes are employed in the reaction, two regioisomeric allylic alcohols are produced. The regioselectivity of the reaction depends on the steric and electronic effects of the substituents on the acetylenes. For example, treatment of tantalum-alkyne complexes derived from methyl alkynyl sulfides with carbonyl compounds yields (E)-3-hydroxy-1-propenyl methyl sulfides in a regioselective manner. Tantalum-alkyne complexes derived from acetylenic esters react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z-isomers of trisubstituted alpha,beta-unsaturated esters. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds predominantly at the beta-position of the amides. The regioselectivity of the reaction between acetylenic amides and aldehydes, however, cannot be explained solely in terms of the steric and electronic effects of the substituents. Strong coordination of the amide group to the tantalum center could also be responsible for the observed selectivity, which is opposite to that observed with tantalum-acetylenic ester complexes.
• Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides­
  作者：Kang Park、Balaji Mohan、Sori Hwang、Hyunje Woo

  DOI：10.1055/s-0035-1560458

  日期：——

  for copper nanoparticle catalyzed ligand-free S–Csp bond formation was developed by using dimethyl sulfoxide as the solvent, a base, and molecular oxygen as a green oxidant. This study provides a new catalytic route for the production of alkynyl sulfides through dual activation of S–S and C–H bonds. A wide range of alkynyl sulfides were synthesized on a large scale with a low catalyst loading (0.5 mol%

  摘要 通过使用二甲基亚砜作为溶剂，碱和分子氧作为绿色氧化剂，开发了一种有效的铜纳米颗粒催化无配体SC键形成的方法。这项研究为通过S–S和C–H键的双重活化生产炔基硫化物提供了一条新的催化途径。以低催化剂负载量（0.5mol％Cu）大规模合成了各种各样的炔基硫化物。这种合成方法也可以扩展到硒化物，而碲化物在没有催化剂的情况下进行类似的反应。 通过使用二甲基亚砜作为溶剂，碱和分子氧作为绿色氧化剂，开发了一种有效的铜纳米颗粒催化无配体SC键形成的方法。这项研究为通过S–S和C–H键的双重活化生产炔基硫化物提供了一条新的催化途径。以低催化剂负载量（0.5mol％Cu）大规模合成了各种各样的炔基硫化物。这种合成方法也可以扩展到硒化物，而碲化物在没有催化剂的情况下进行类似的反应。
• One-pot synthesis of mixed ( )-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel β-organylthio vinyllithium intermediates
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Marco A. Pereira、Adriano C.M. Baroni、Francisco A. Marques、Paulo R. de Oliveira、Palimécio G. Guerrero

  DOI：10.1016/j.tetlet.2010.07.112

  日期：2010.9

  One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved.