3-(2'-hydroxy-5'-methylphenyl)cyclohex-1-ene | 17960-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(2'-hydroxy-5'-methylphenyl)cyclohex-1-ene
• 英文别名: 2-cyclohexenyl-4-methyl phenol；2-Cyclohex-2-en-1-yl-4-methylphenol
• CAS: 17960-09-7
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: UCJUWXYHDKQRCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-(2'-hydroxy-5'-methylphenyl)cyclohex-1-ene 在 hexamethylene tetramine hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以98%的产率得到13-Bromo-4-methyl-8-oxa-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene
  参考文献：
  名称：

  Hexamethylene Tetramine Hyorotribromide Mediated Regioselective Cyclisation ofOrtho- Cyclohexenyl Phenols^#

  摘要：

  Hexamethylene tetramine hydrotribromide is found to be superior to pyridine hydrotribromide when compared with the rate of reaction and chemoselectivity for the regioselective cyclisation of a number of ortho-cyclohexenyl phenols 1(a-j) to 3-bromo-2,4-propano-chromans 2(a-j).

  DOI：

  10.1080/00397919608003693
• 作为产物：
  描述：

  1-(cyclohex-2-en-1-yloxy)-4-methylbenzene 以 various solvent(s) 为溶剂， 反应 16.0h， 以77%的产率得到3-(2'-hydroxy-5'-methylphenyl)cyclohex-1-ene
  参考文献：
  名称：

  Majumdar, Krishna C.; Kundu, Anup K., Canadian Journal of Chemistry, 1995, vol. 73, # 10, p. 1727 - 1732

  摘要：

  DOI：

文献信息

• Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics
  作者：Andrei V. Malkov、Stuart L. Davis、Ian R. Baxendale、William L. Mitchell、Pavel Kočovský

  DOI：10.1021/jo982178y

  日期：1999.4.1

  The stable, readily available molybdenum(II) complexes [Mo(CO)(4)Br-2](2) (B) and Mo(CO)(3)(MeCN)(2)(SnCl3)Cl (C) have been found to catalyze C-C bond-forming allylic substitution with electron-rich aromatics (e.g., 15 + PhOMe --> 62) and heteroaromatics (e.g., 15 + 36 --> 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.
• Cyclisation of<i>Ortho</i>-Cyclohexenyl Phenols<i>via</i>Epoxidation^#
  作者：K. C. Majumdar、P. Chatterjee、A. K. Kundu

  DOI：10.1080/00397919608004643

  日期：1996.9

  A number of ortho-cyclohexenyl phenols 2(a-i) have been cyclised by treatment with one equivalent of m-chloroperoxybenzoic acid in refluxing benzene for 4 h to furnish linearly fused 1-hydroxy-1,2,3,4,4a,9a-hexahydrodibenzofurans 3 (a-i) (70-80%) and bicyclic 3-hydroxy-1,3-ethanochromans 4(a-f) (10-20%). Products 3(a-i) were oxidised with 2,3-dichloro-5,6-dicyano-1 ,4-benzoquinone (excess) in refluxing dry xylene for 6 h to give 2,3-dihydrodibenzofuran-1 (2H)-ones 6(a-i) (85-95%).
• <i>N</i>-IODOSUCCINIMIDE MEDIATED REGIOSELECTIVE HETEROCYCLIZATION OF <i>o</i>-CYCLOHEX-2′-ENYL PHENOLS
  作者：K. C. Majumdar、P. K. Basu

  DOI：10.1081/scc-120015388

  日期：2002.1.1

  A number of 3,4-benzo-9-iodo-2-oxabicyclo[3.3.1]nonanes (2a-f) are synthesized in excellent yields by regioselective heterocyclization of o-cyclohex-2'-enyl phenols (1a-f) with N-iodosuccinimide in acetonitrile at 0-5degreesC.