2-[(1-cyclohexenyl)ethynyl]phenyl isocyanate | 315179-80-7

• 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: 2-[(1-cyclohexenyl)ethynyl]phenyl isocyanate
• 英文别名: 1-cyclohex-1-enylethynyl-2-isocyanatobenzene；1-[2-(Cyclohexen-1-yl)ethynyl]-2-isocyanatobenzene
• CAS: 315179-80-7
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: DDWLVRXBGGXBBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1-cyclohexenyl)ethynyl]phenyl isocyanate 以 xylene 为溶剂， 反应 13.5h， 生成 11-(1-cyclohexenyl)-6H-indolo[2,3-b][1,5]naphthyridine
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e
• 作为产物：
  描述：

  苯甲酸,2-(1-环己烯-1-基乙炔基)-,甲基酯 在 sodium hydroxide 、 二苯基磷酸 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.0h， 生成 2-[(1-cyclohexenyl)ethynyl]phenyl isocyanate
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e

文献信息

• Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives
  作者：Takao Saito、Yoshihiko Sonoki、Takashi Otani、Noriki Kutsumura

  DOI：10.1039/c4ob00825a

  日期：——

  A new approach towards the synthesis of indole derivatives via triflic acid-promoted cycloisomerization with rearrangement of 2-(alkyn-1-yl)phenyl isothiocyanates and 2-(alkyn-1-yl)phenyl isocyanates has been achieved. By this methodology, structurally diverse types of indole derivatives such as thieno- and furo-indoles, spiro-indolethiones, spiro-oxindoles, and 3-alkylidene-oxindoles were synthesized

  已经实现了通过三氟甲磺酸促进的环异构化并重排2-（炔-1-基）苯基异硫氰酸酯和2-（炔-1-基）苯基异氰酸酯来合成吲哚衍生物的新方法。通过这种方法，合成了结构上不同类型的吲哚衍生物，例如噻吩-和呋喃-吲哚，螺-吲哚硫酮，螺-羟吲哚和3-亚烷基-氧吲哚。
• Synthesis of 6<i>H</i>-Indolo[2,3-<i>b</i>][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids
  作者：Quan Zhang、Chongsheng Shi、Hai-Ren Zhang、Kung K. Wang

  DOI：10.1021/jo000978e

  日期：2000.11.1

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.