3-cyclohex-1-en-1-yl-1-(4-ethoxyphenyl)prop-2-yn-1-ol | 1262587-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-cyclohex-1-en-1-yl-1-(4-ethoxyphenyl)prop-2-yn-1-ol
• 英文别名: 3-(Cyclohexen-1-yl)-1-(4-ethoxyphenyl)prop-2-yn-1-ol
• CAS: 1262587-75-6
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: VPIWVCKRXFAKIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclohex-1-en-1-yl-1-(4-ethoxyphenyl)prop-2-yn-1-ol 、 N-cyclopropyl-1H-indole-2-carboxamide 在 碘 作用下， 以 乙腈 为溶剂， 以52%的产率得到2-cyclopropyl-3-cyclohex-1-enyl-4-iodo-5-(4-ethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one
  参考文献：
  名称：

  Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization PathwayCDRI Communication No. 8094

  摘要：

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.

  DOI：

  10.1021/jo201228t
• 作为产物：
  描述：

  1-乙炔基环己烷 、 4-乙氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以76%的产率得到3-cyclohex-1-en-1-yl-1-(4-ethoxyphenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization PathwayCDRI Communication No. 8094

  摘要：

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.

  DOI：

  10.1021/jo201228t

文献信息

• Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination
  作者：Sudhir K. Sharma、Sahaj Gupta、Mohammad Saifuddin、Anil K. Mandadapu、Piyush K. Agarwal、Harsh M. Gauniyal、Bijoy Kundu

  DOI：10.1016/j.tetlet.2010.10.147

  日期：2011.1

  Two simple, highly efficient three component tandem reactions for the synthesis of diversified N-a N-b dicarbamate-4,9-dihydro-3-iodo-alpha-carbolines and N-a-carbamate-3-iodo-alpha-carbolines have been described. The strategy involves one-pot condensation of bis-carbamate protected 2-amino indoles with disubstituted propargyl alcohols and I-2/ICl. The salient feature of the reaction involves iodocyclo-elimination of N-b-linked carbamate under mild condition in the final step. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-<i>endo</i>-<i>dig</i> Iodo-Cyclization PathwayCDRI Communication No. 8094
  作者：Sudhir K. Sharma、Anil K. Mandadapu、Brijesh Kumar、Bijoy Kundu

  DOI：10.1021/jo201228t

  日期：2011.8.19

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.