2-(1-己炔基)苯基异硫氰酸酯 | 1008495-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(1-己炔基)苯基异硫氰酸酯
• 英文名称: 2-(1-hexynyl)phenyl isothiocyanate
• 英文别名: 1-Hex-1-ynyl-2-isothiocyanatobenzene；1-hex-1-ynyl-2-isothiocyanatobenzene
• CAS: 1008495-34-8
• 化学式: C₁₃H₁₃NS
• 分子量: 215.319
• InChiKey: TUXFHYCNBOUXGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-己炔基)苯基异硫氰酸酯 在 碘 、 caesium carbonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 (4E)-2-(N,N-diethylamino)-4-(1-iodopentylidene)-4H-benzo[d][1,3]thiazine
  参考文献：
  名称：

  Studies on chalcogen-containing heterocycles. Part 38: Regio- and stereoselective tandem addition–iodocyclization of 2-ethynylphenyl isothiocyanates with N- and O-nucleophiles affording 4-(iodoalkylidene)benzo[d][1,3]thiazines

  摘要：

  The treatment of the o-ethynylphenyl isothiocyanates with primary and secondary amines in 1,2-DCE, followed by the addition of 12 and then heating resulted in the regio- and stereoselective tandem addition-iodocyclization to give the (4E)-2-amino-4-(1-iodomethylidene)benzo[d][1,3]thiazine derivatives as the sole product in high yields via the 6-exo-dig mode cyclization. The 2-alkoxy-1,3-benzothiazines were similarly produced from the o-ethynylphenyl isothiocyanates and the corresponding sodium alkoxides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.069
• 作为产物：
  描述：

  二硫化碳 、 2-(1-hexynyl)-N-(triphenylphosphonylidene)benzeneamine 反应 12.0h， 以99%的产率得到2-(1-己炔基)苯基异硫氰酸酯
  参考文献：
  名称：

  Thiocarbonyl induced heterocumulenic Pauson–Khand type reaction: expedient synthetic method for thieno[2,3-b]indol-2-ones

  摘要：

  首次描述了由CS诱导的Pauson–Khand类型反应；2-烷基炔基苯异硫氰酸酯在摩尔比为1的Mo(CO)6或Co2(CO)8的存在下，或在碳 monoxide气氛下使用催化量的Rh催化剂，转化为3取代的2H-噻吩[2,3-b]吲哚-2-酮。

  DOI：

  10.1039/b712739a

文献信息

• Tandem addition–cyclization of o-ethynylphenyl isothiocyanates with N nucleophiles; difference of cyclization mode between primary and secondary amines
  作者：Mamoru Kaname、Haruki Sashida

  DOI：10.1016/j.tetlet.2011.11.133

  日期：2012.2

  mode cyclization of the N-(2-ethynylphenyl)thioureas, which were easily obtained from the o-ethynylphenyl isothiocyanates and the primary amines, to provide the 2-imino-4-methylidene-1H-benzo[d][1,3]thiazines as the sole product in excellent yields. The secondary amines reacted with the o-ethynylphenyl isothiocyanates to give both the 6-exo and 5-endo-dig mode cyclization products under the same conditions

  三氟甲磺酸银促进了N-（2-乙炔基苯基）硫脲的6-exo-dig模式环化反应，这是很容易从邻乙炔基苯基异硫氰酸酯和伯胺获得的，从而提供了2-亚氨基-4-亚甲基-1 H作为唯一产品​​的-苯并[ d ] [1,3]噻嗪具有极好的收率。仲胺与邻乙炔基苯基异硫氰酸酯在相同条件下反应，生成6-exo和5-endo-dig模式环化产物。
• Synthesis of Quinoline-2-thiones via Tandem Indium(III)-Promoted Friedel−Crafts Alkenylation−Cyclization of 2-Alkynylphenyl Isothiocyanates
  作者：Takashi Otani、Shinichi Kunimatsu、Hiroshi Nihei、Yuko Abe、Takao Saito

  DOI：10.1021/ol7024668

  日期：2007.12.1

  A new approach to the synthesis of 4-aryl- or 4-arylthioquinoline-2-thiones via indium(111) reagent-mediated tandem Friedel-Crafts alkenylationcyclization of 2-alkynylphenyl isothiocyanates is described.
• Thiocarbonyl induced heterocumulenic Pauson–Khand type reaction: expedient synthetic method for thieno[2,3-b]indol-2-ones
  作者：Takao Saito、Hiroshi Nihei、Takashi Otani、Toshiyuki Suyama、Naoki Furukawa、Masatoshi Saito

  DOI：10.1039/b712739a

  日期：——

  The first examples of CS induced Pauson–Khand type reactions are described; 2-alkynylphenyl isothiocyanates were converted to 3-substituted-2H-thieno[2,3-b]indol-2-ones in the presence of a stoichiometric amount of Mo(CO)6 or Co2(CO)8, or a catalytic amount of Rh catalyst under an atmospheric pressure of carbon monoxide.

  首次描述了由CS诱导的Pauson–Khand类型反应；2-烷基炔基苯异硫氰酸酯在摩尔比为1的Mo(CO)6或Co2(CO)8的存在下，或在碳 monoxide气氛下使用催化量的Rh催化剂，转化为3取代的2H-噻吩[2,3-b]吲哚-2-酮。
• Studies on chalcogen-containing heterocycles. Part 38: Regio- and stereoselective tandem addition–iodocyclization of 2-ethynylphenyl isothiocyanates with N- and O-nucleophiles affording 4-(iodoalkylidene)benzo[d][1,3]thiazines
  作者：Haruki Sashida、Mamoru Kaname、Mao Minoura

  DOI：10.1016/j.tet.2013.05.069

  日期：2013.8

  The treatment of the o-ethynylphenyl isothiocyanates with primary and secondary amines in 1,2-DCE, followed by the addition of 12 and then heating resulted in the regio- and stereoselective tandem addition-iodocyclization to give the (4E)-2-amino-4-(1-iodomethylidene)benzo[d][1,3]thiazine derivatives as the sole product in high yields via the 6-exo-dig mode cyclization. The 2-alkoxy-1,3-benzothiazines were similarly produced from the o-ethynylphenyl isothiocyanates and the corresponding sodium alkoxides. (C) 2013 Elsevier Ltd. All rights reserved.