4-(4-benzylpiperidin-1-yl)-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile | 933463-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(4-benzylpiperidin-1-yl)-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile
• 英文别名: 4-(4-Benzylpiperidin-1-yl)-2-oxo-5,6-dihydrobenzo[h]chromene-3-carbonitrile
• CAS: 933463-33-3
• 化学式: C₂₆H₂₄N₂O₂
• 分子量: 396.489
• InChiKey: VUKAUKUIERSMIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-benzylpiperidin-1-yl)-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile 、 (-)-香茅醛 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到1-(4-benzylpiperidin-1-yl)-4-[(2S)-6-methylhept-5-en-2-yl]-9,10-dihydrophenanthrene-2-carbonitrile
  参考文献：
  名称：

  An expeditious protocol for sesquiterpene-cored functionalized arenes from S-(−)-citronellal

  摘要：

  An expeditious straightforward synthesis of sesquiterpene-cored arenes functionalized with electron-withdrawing or electron-donating substituents is described and illustrated by Michael addition of S(-)-citronellal on functionalized 2H-pyran-2-one in a single step at room temperature. The reaction was further generalized by synthesizing isoprenylated 9,10-dihydrophenanthrene-2-carbonitrile using 5,6-dihydro-2-oxo-4-sec-amino-2H-benzo[h]chromene-3-carbonitriles and S-(-)-citronellal under similar reaction conditions. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.117
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 氢氧化钾 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 4-(4-benzylpiperidin-1-yl)-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile
  参考文献：
  名称：

  2-氧代苯并[ h ]色烯：简洁高效合成茚并[1,2- c ]菲的新途径

  摘要：

  通过4-秒-氨基-2-的碱催化环转化，描述了一种7-秒-氨基-5,13-二氢-6 H-茚并[1,2 - c ]菲-8腈的高效简捷合成方法。带有1-茚满酮的oxo-5,6-dihydro-2 H-苯并[ h ]苯并3-亚甲腈，产率中等至良好。

  DOI：

  10.1016/j.tetlet.2007.04.087

文献信息

• An unusual synthesis of tetrahydrobenzo[f]isoquinolines
  作者：Ramendra Pratap、Resmi Raghunandan、P.R. Maulik、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2007.09.059

  日期：2007.11

  A facile and short synthesis of 2-oxo-4-sec-amino-2,3,5,6-tetrahydrobenzo[f]isoquinoline-1-carbonitriles has been delineated through base catalyzed ring transformation of 5,6-dihydro-2-oxo-4-sec-amino-2H-benzo[h]chromene-3-carbonitrile by cyanoacetamide in excellent yields.

  通过5,6-二氢-2-的碱催化环转化，描述了2-氧代-4-仲-氨基-2,3,5,6-四氢苯并[ f ]异喹啉-1-腈的简便快速合成方法氰基乙酰胺制备的oxo-4-仲-氨基-2 H-苯并[ h ]亚甲基-3-甲腈具有优异的收率。
• An efficient non-catalytic, regioselective approach to the synthesis of angularly fused polycyclic systems
  作者：Ramendra Pratap、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2009.04.122

  日期：2009.7

  of 4-sec.amino-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles by a carbanion, generated in situ from cyclopentanone, cyclohexanone, cycloheptanone, and cyclooctanone separately in good yields. An increase in the size of cycloalkanone ring beyond cyclooctanone restricts the ring transformation under analogous reaction conditions possibly due to bulky conformation of higher homologs. The synthetic

  秒合成PAH类似物部分还原的不同环尺寸的新颖方法。通过环戊酮原位生成的碳负离子，通过碱诱导的4 - sec .amino-2-oxo-5,6-dihydro-2 H-苯并[ h ]色烯-3-腈的环诱导的环氧基描述了氨基和腈的官能团，环己酮，环庚酮和环辛酮的收率很好。在类似的反应条件下，环烷酮环的尺寸增加到超过环辛酮会限制环的转化，这可能是由于较高的同系物的庞大构象所致。合成方法为构建有角稠合的部分还原的多环芳烃提供了一条有效的通用途径：5-秒 氨基-2,3,6,7-四氢-1 H-环戊[ c ]菲-4-腈，6秒。氨基-2,3,4,7,8-五氢-1 H-苯并[ c ]菲-5腈，7- sec。氨基-2,3,4,5,8,9-六氢-1 H-环庚[ c ]菲-6腈和8 sec。氨基-2,3,4,5,6,9,10-七氢-1 H-环辛基[ c ]菲-7腈。
• A convenient synthesis of partially reduced benzo[c]phenanthrenes, its ketals and ketones
  作者：Ramendra Pratap、Resmi Raghunandan、Abhishek Kumar Mishra、P.R. Maulik、V.P. Gupta、Vishnu Ji Ram

  DOI：10.1016/j.tet.2009.12.026

  日期：2010.2

  cyclohexanone, 2-cyclohexen-1-one, 1,4-cyclohexanedione monocycloalkene ketals. The acid catalyzed deketalation of 6-sec-amino-3,4,7,8-tetrahydro-1H-benzo[c]phenanthrene-2-one-carbonitrile ketals led to yield 6-sec-amino-3,4,7,8-tetrahydro-1H-benzo[c]phenanthrene-3-carbonitrile-2-ones in excellent yield. We also performed the X-ray studies of the molecules 3d and 6a to know the degree of non-planarity

  简捷方便地合成各种部分还原的6 - sec-氨基-1,2,3,4,7,8-六氢-，6 - sec-氨基-1,2,7,8-四氢苯并[ c ]菲-通过以下方法描述了5-腈，6-仲-氨基-3,4,7,8-四氢-1 H-苯并[ c ]菲-2--2-酮-5-腈环烯烃缩酮，带有电子供体和受体取代基的侧基。环己酮，2-环己烯-1-酮，1,4-环己二酮单环烯烃对2-氧代-4-仲-氨基-5,6-二氢-2 H-苯并[ h ]亚甲基-3-甲腈的碱催化环转化缩酮。酸催化的脱缩酮反应6秒钟-氨基-3,4,7,8-四氢- 1 H ^ -苯并[ c ^ ]菲-2-酮甲腈导致得到6-缩酮仲丁基-氨基-3,4,7,8-四氢ħ -苯并[ c ]菲-3-甲腈-2-酮，收率极高。我们还对分子3d和6a进行了X射线研究，以了解非平面度。
• An Efficient De Novo Synthesis of Partially Reduced Phenanthrenes through C−C Insertion
  作者：Ramendra Pratap、Vishnu Ji Ram

  DOI：10.1021/jo0711079

  日期：2007.9.1

  5,6-dihydro-2-oxo-4-sec-amino-2H-benzo[h]chromene-3-carbonitrile by carbanion derived in situ from various ketones in moderate to good yields. 9,10-Dihydrophenanthrenes with and without substituent in the bay region are efficiently and regioselectively synthesized by using propanal and acetyltrimethylsilane as a source of carbanion. Even the synthesis of bisphenanthrenes has been achieved by the ring

  一种高效且新颖的合成高度拥挤的3-烷基-，4-烷基-，3-芳基-，3,4-二烷基-，4-烷基-3-芳基-和3,4-二芳基-9的方法，10-二氢-1-仲丁基-aminophenanthrene -2-腈已经通过5,6-二氢-2-氧代-4-碱催化环转化划定仲丁基氨基-2- ħ苯并[ ħ ]苯并吡喃从碳酮中衍生出各种羰基的3-甲腈，产率中等至良好。通过使用丙醛和乙酰基三甲基硅烷作为碳负离子的来源，可以高效地进行区域选择性合成9,10-二氢菲，并在海湾区域内进行取代。甚至bisphenanthrenes的合成已经由5,6-二氢-2-氧代-4-的环转化实现秒2-乙酰基菲以中等收率得到-氨基-2 H-苯并[ h ]亚甲基-3-甲腈。高取代度的3-氨基-1-仲氨基-5,6-二氢菲-2,4-二腈也已经由2-氧代苯并[ h ]色烯与丙二腈的反应制备。
• A non-catalytic approach to the synthesis of 5,6-dihydrobenzo[h]quinolines
  作者：Ramendra Pratap、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2007.02.049

  日期：2007.4

  A concise synthesis of highly functionalized 5,6-dihydrobenzo[h]quinoline-3-carbonitriles is delineated through base induced ring transformation of 4-sec-amino-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles with S-methylisothiourea sulfate and 1-carboxamidinepyrazole hydrochloride, separately, in DMF. Under analogous reaction conditions the ring transformation of 4-sec-amino-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles by formamidine acetate provided 4-sec-amino-benzo[h]quinoline-3-carbonitriles in moderate yields, while with benzamidine hydrochloride, the reaction followed the same mechanism to yield 2-phenyl-4-sec-amino-5,6-dihydrobenzo[h]quinoline-3-carbonitriles. (c) 2007 Elsevier Ltd. All rights reserved.