(Z)-1-phenyl-7-hydroxy-3-heptene-1,5-diyne | 702706-45-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-1-phenyl-7-hydroxy-3-heptene-1,5-diyne
• 英文别名: (Z)-7-phenylhept-4-en-2,6-diyn-1-ol
• CAS: 702706-45-4
• 化学式: C₁₃H₁₀O
• 分子量: 182.222
• InChiKey: NVGMZSGAKOQLIX-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-phenyl-7-hydroxy-3-heptene-1,5-diyne 在 吡啶 、 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (Z)-1-phenyl-7-(phenylsulfonyl)-3-heptene-1,5-diyne
  参考文献：
  名称：

  Substituent effects on the cyclization mode of 7-sulfonyl-3-hepten-1,5-diynes and 11-sulfonylundeca-3,7-dien-1,5,9-triynes

  摘要：

  In probing of cycloaromatization of 7-phenylsulfonyl-3-hepten-1,5-diyne systems to generate biradical intermediates under an alkaline condition suggested that the aryl moiety on C3-C4 also plays an important role to switch the Myers cyclization to Schmittel cyclization in the allen-enyne system, although the aryl group on the alkyne terminus does not work in the proceeding of the cycloaromatization. For example, treatment of 1-phenyl-7-phenylsulfonyl-3-hepten-1,5-diyne (8) with triethylamine in the presence of 1 4-cyclohexadiene in benzene offered biphenyl 13 in 51% yield. Under the same reaction conditions, cyclization of 1-(2-phenylethynyl)-2-(3-phenylsulfonyl-1-propynyl) benzene (28) gave naphthalene 34 in 42% yield along with indene 35 in 32% yield. Moreover, the substituent effect also occurred in the cyclization of 11-phenylsulfonylundeca-3,7-diene-1,5,9-triyne (38). which provided indene 39 in 50% yield as the major product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.067
• 作为产物：
  描述：

  (Z)-1-choro-5-<(2-tetrahydropyranyl)oxy>-1-penten-3-yne 在 copper(l) iodide 、 四(三苯基膦)钯 、 camphor-10-sulfonic acid 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.0h， 生成 (Z)-1-phenyl-7-hydroxy-3-heptene-1,5-diyne
  参考文献：
  名称：

  Substituent effects on the cyclization mode of 7-sulfonyl-3-hepten-1,5-diynes and 11-sulfonylundeca-3,7-dien-1,5,9-triynes

  摘要：

  In probing of cycloaromatization of 7-phenylsulfonyl-3-hepten-1,5-diyne systems to generate biradical intermediates under an alkaline condition suggested that the aryl moiety on C3-C4 also plays an important role to switch the Myers cyclization to Schmittel cyclization in the allen-enyne system, although the aryl group on the alkyne terminus does not work in the proceeding of the cycloaromatization. For example, treatment of 1-phenyl-7-phenylsulfonyl-3-hepten-1,5-diyne (8) with triethylamine in the presence of 1 4-cyclohexadiene in benzene offered biphenyl 13 in 51% yield. Under the same reaction conditions, cyclization of 1-(2-phenylethynyl)-2-(3-phenylsulfonyl-1-propynyl) benzene (28) gave naphthalene 34 in 42% yield along with indene 35 in 32% yield. Moreover, the substituent effect also occurred in the cyclization of 11-phenylsulfonylundeca-3,7-diene-1,5,9-triyne (38). which provided indene 39 in 50% yield as the major product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.067

文献信息

• Substituent effects on the cyclization mode of 7-sulfonyl-3-hepten-1,5-diynes and 11-sulfonylundeca-3,7-dien-1,5,9-triynes
  作者：Huey-Juan Wu、Chi-Fong Lin、Jeng-Lin Lee、Wen-Der Lu、Chia-Ying Lee、Chin-Chau Chen、Ming-Jung Wu

  DOI：10.1016/j.tet.2004.02.067

  日期：2004.4

  In probing of cycloaromatization of 7-phenylsulfonyl-3-hepten-1,5-diyne systems to generate biradical intermediates under an alkaline condition suggested that the aryl moiety on C3-C4 also plays an important role to switch the Myers cyclization to Schmittel cyclization in the allen-enyne system, although the aryl group on the alkyne terminus does not work in the proceeding of the cycloaromatization. For example, treatment of 1-phenyl-7-phenylsulfonyl-3-hepten-1,5-diyne (8) with triethylamine in the presence of 1 4-cyclohexadiene in benzene offered biphenyl 13 in 51% yield. Under the same reaction conditions, cyclization of 1-(2-phenylethynyl)-2-(3-phenylsulfonyl-1-propynyl) benzene (28) gave naphthalene 34 in 42% yield along with indene 35 in 32% yield. Moreover, the substituent effect also occurred in the cyclization of 11-phenylsulfonylundeca-3,7-diene-1,5,9-triyne (38). which provided indene 39 in 50% yield as the major product. (C) 2004 Elsevier Ltd. All rights reserved.