8-Methoxy-4-(4-methylpiperidin-1-yl)-2-oxo-5,6-dihydrobenzo[h]chromene-3-carbonitrile | 933463-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 8-Methoxy-4-(4-methylpiperidin-1-yl)-2-oxo-5,6-dihydrobenzo[h]chromene-3-carbonitrile
• CAS: 933463-35-5
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: DBLFDAJRVKBRNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-Methoxy-4-(4-methylpiperidin-1-yl)-2-oxo-5,6-dihydrobenzo[h]chromene-3-carbonitrile 、 1-茚酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到18-Methoxy-12-(4-methylpiperidin-1-yl)pentacyclo[11.8.0.02,10.04,9.016,21]henicosa-1(13),2(10),4,6,8,11,16(21),17,19-nonaene-11-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
• 作为产物：
  描述：

  6-甲氧基-1-萘满酮 在 氢氧化钾 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 8-Methoxy-4-(4-methylpiperidin-1-yl)-2-oxo-5,6-dihydrobenzo[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。
• Synthesis of Highly Functionalized Spirobutenolides via a Nitroalkane-Mediated Ring Contraction of 2-Oxobenzo[<i>h</i>]chromenes through Denitration
  作者：Amr Elagamy、Ranjay Shaw、Rahul Panwar、Shally、Vishnu Ji Ram、Ramendra Pratap

  DOI：10.1021/acs.joc.8b02257

  日期：2019.2.1

  spirobutenolides was carried out by a nitroalkane carbanion-induced ring opening and relactonization via a denitration reaction of 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles and 2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles. However, when nitroethane was used as a nucleophile source in lieu of nitromethane, a mixture of (E)- and (Z)-isomers of the corresponding spirobutenolides

  通过2-烷氧基-5,6-二氢-2 H-苯并[ h ]亚甲基-3-腈和2-腈的反硝化反应，通过硝基烷碳负离子诱导的开环和再乳化，轻松合成高度官能化的螺丁烯内酯氧代2，5-二氢硫代色素[4，3- b ]吡喃-3-腈。然而，当使用硝基乙烷代替硝基甲烷作为亲核试剂源时，以不同的比例获得了相应的螺丁烯内酯的（E）-和（Z）-异构体的混合物。通过单晶X射线衍射确认产物的结构和几何形状。隔离的（E）-和（Z室温下用乙醇钠在DMF中处理的1）-丁烯内酯通过烯丙基开环随后脱羧提供高度取代的三烯。
• Step-wise and one-pot synthesis of highly substituted conjugated trienes from 2-oxobenzo[<i>h</i>]chromenes/2<i>H</i>-pyran-2-ones
  作者：Amr Elagamy、Ismail Althagafi、Ramendra Pratap

  DOI：10.1039/d1ob00314c

  日期：——

  been developed for the construction of trienes. The mixture of the (E)- and (Z)-isomers of spirobutenolides undergoes decarboxylative rearrangement in the presence of sodium ethoxide as a base to yield the (E)-isomer of trienes, while the (E)-isomer of butenolides reacts to give a mixture of (2E,4E)- and (2E,4Z)-isomers of trienes in an almost steady ratio of 45 : 55 or 1 : 1.2. The structure and geometry

  描述了通过硝基乙烷介导的 2-氧代苯并[ h ]色烯/2 H-吡喃-2-酮的环收缩，然后对所得螺丁烯内酯和丁烯内酯进行脱羧重排，合成共轭三烯的温和有效途径。三烯的( E )-异构体是通过逐步和一锅法从2-氧代苯并[ h ]色烯中获得的。丁烯内酯4a-l作为新的底物已被开发用于构建三烯。螺丁烯内酯的 ( E )- 和 ( Z )-异构体的混合物在乙醇钠作为碱存在下发生脱羧重排产生 ( E ))-三烯异构体，而丁烯内酯的 ( E )-异构体反应生成 (2 E ,4 E )- 和 (2 E ,4 Z )-三烯异构体的混合物，比例几乎稳定为 45 : 55或 1：1.2。所得丁烯内酯和三烯的结构和几何形状通过单晶 X 射线分析得到证实。
• An expeditious protocol for sesquiterpene-cored functionalized arenes from S-(−)-citronellal
  作者：Atul Goel、Deepti Verma

  DOI：10.1016/j.tetlet.2009.02.117

  日期：2009.5

  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.
• 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.