3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one | 1404440-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one
• 英文别名: 3-(5-phenylpent-4-yn-1-yl)cyclohex-2-enone；3-(5-Phenylpent-4-ynyl)cyclohex-2-en-1-one；3-(5-phenylpent-4-ynyl)cyclohex-2-en-1-one
• CAS: 1404440-58-9
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: BWDZTAJUFRCRFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one 在 iron(III) chloride 、 sodium hydride 作用下， 以 二甲基亚砜 、 1,2-二溴乙烷 为溶剂， 反应 17.5h， 生成 (E)-1-(chlorophenylmethylene)spiro[4.6]undecan-8-one
  参考文献：
  名称：

  Synthesis of 2-Azaspiro[4.6]undec-7-enes from N-Tosyl-N-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols

  摘要：

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

  DOI：

  10.1021/jo301764g
• 作为产物：
  描述：

  3-甲氧基-2-环己烯-1-酮 、 (5-iodopent-1-yn-1-yl)benzene 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 13.0h， 以82%的产率得到3-(5-phenylpent-4-yn-1-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Synthesis of 2-Azaspiro[4.6]undec-7-enes from N-Tosyl-N-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols

  摘要：

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

  DOI：

  10.1021/jo301764g

文献信息

• Facile Synthesis of Spirocyclic Ketones via Gold(I)-Catalyzed Claisen-Type Rearrangement of Cyclic 8-Aryl-2,7-enyn-1-ols
  作者：Ming-Chang P. Yeh、Hui-Fen Pai、Chuen-Yo Hsiow、Yan-Rong Wang

  DOI：10.1021/om900833k

  日期：2010.1.11

  The gold(I)-catalyzed Claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-1-ols proceeds via a cationic allylic vinyl ether gold intermediate to give spirocyclic ketones. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate the spirocyclic ketones. This transformation can be applied to the synthesis of aza-

  环状八-芳基-2,7-烯基-1-醇的金（I）催化的克莱森型重排通过阳离子烯丙基乙烯基醚金中间体进行，得到螺环酮。该反应通过羟基攻击金活化的炔烃上进行，然后进行[3,3]-σ重排以生成螺环酮。该转化可用于由在系链和金（I）催化剂中带有N-磺酰胺或氧原子键的环状8-芳基-2,7-烯炔-1-醇合成氮杂和氧杂螺环酮。
• Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols
  作者：Ming-Chang P. Yeh、Cheng-Wei Fang、Hsin-Hui Lin

  DOI：10.1021/ol300434m

  日期：2012.4.6

  A simple and efficient FeCl3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 degrees C in air to afford (Z)-4-(arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl3.
• Diastereoselective Synthesis of 2-Arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via FeCl₃·6H₂O-Catalyzed Spiroannulation/Hydride Transfer of 6-(5-Arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols
  作者：Hsin-Hui Lin、Kuan-Yi Lee、Yin-An Chen、Chi-Fan Liu、Ming-Chang P. Yeh

  DOI：10.1021/jo5023266

  日期：2014.12.5

  In the presence of a catalytic amount of FeCl3 center dot 6H(2)O, 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols underwent attack of the pendant acetylene at the iron-activated oxirane to give a vinylic carbocation. Hydride transfer from the carbinol carbon to the newly formed cation center furnished 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones in excellent stereoselectivity and good yields.
• Synthesis of 2-Azaspiro[4.6]undec-7-enes from <i>N</i>-Tosyl-<i>N</i>-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols
  作者：Ming-Chang P. Yeh、Chia-Jung Liang、Chern-Wei Fan、Wei-Hang Chiu、Jun-Yuan Lo

  DOI：10.1021/jo301764g

  日期：2012.11.2

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.