1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone | 30414-95-0

• 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: 1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone
• 英文别名: isoencecalin；1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)-ethanone；1-(5-Methoxy-2,2-dimethylchromen-6-yl)ethanone
• CAS: 30414-95-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: NQTRXUYMPWDISO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone 在 Mn(III)salen <(S,S)-4> sodium hypochlorite 作用下， 以 二氯甲烷 为溶剂， 生成 1-((1aS,7bS)-7-Methoxy-2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalen-6-yl)-ethanone
  参考文献：
  名称：

  Enantiomerically Pure Epoxychromans via Asymmetric Catalysis

  摘要：

  A practical and highly effective process for the asymmetric epoxidation of several 2,2-dimethylchromene derivatives is reported. Catalysis by Mn(salen) complex 4 in all cases affords epoxychromans with > 90% ee, and this method has been applied to the synthesis of two recently developed antihypertensive agents in enantiomerically pure form.

  DOI：

  10.1016/s0040-4039(00)93426-9
• 作为产物：
  描述：

  β-tubaic acid 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 15.0h， 生成 1-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone
  参考文献：
  名称：

  A New Route to the Synthesis of Pyranoflavone and Pyranochalcone Natural Products and their Derivatives

  摘要：

  从2H-吡喃出发，完成了生物活性吡喃黄酮天然产物1和2的全合成。本文描述了吡喃查尔酮天然产物，扁柄草素（9）和4-羟基扁柄草素（10）及其衍生物30-32的合成。该合成路线还提供了生物学上有趣的物质，如β-图贝酸（24）、去甲基异黄皮树脂酚（25）和异黄皮树脂酚（27）。

  DOI：

  10.1055/s-2006-926294

文献信息

• Concise Synthetic Approaches to Naturally Occurring β-Hydroxypyranochalcones: First Total Synthesis of Purpurenone, Its Derivative, and Praecansone B
  作者：Xue Wang、Yong-Rok Lee、Sung-Hong Kim

  DOI：10.5012/bkcs.2012.33.8.2647

  日期：2012.8.20

  Analysis Research Division, Daegu Center, Korea Basic Science Institute, Daegu 702-701, KoreaReceived May 1, 2012, Accepted May 14, 2012The total synthesis of biologically interesting β-hydroxypyranochalcones, purpurenone (1), its derivative 2,praecansone B (3), and pongapinone A (4) has been accomplished starting from commercially available 2,4-dihydroxyacetophenone or 6-methoxy-2,4-dihydroxyacetophenone

  韩国基础科学研究所大邱中心分析研究部, Daegu 702-701, Korea 2012年5月1日收稿, 2012年5月14日收稿 具有生物学意义的β-羟基吡喃查尔酮的全合成, purpurenone (1), its衍生物2,praecansone B (3 ) 和 pongapinone A (4) 已经从市售的 2,4-二羟基苯乙酮或 6-甲氧基-2,4-二羟基苯乙酮开始，通过苯并吡喃形成、O-甲基化和偶联反应的收敛策略分 3 步完成。关键词：β-羟基吡喃查耳酮、紫嘌呤酮、Praecanone B、Pongapinone A、苯并吡喃的形成介绍吡喃查耳酮和β-羟基吡喃查耳酮是类黄酮的丰富亚类，在自然界广泛分布。
• The first asymmetric epoxidation using a combination of achiral (salen)manganese(III) complex and chiral amine
  作者：Takashi Hashihayata、Yoshio Ito、Tsutomu Katsuki

  DOI：10.1016/s0040-4020(97)00633-9

  日期：1997.7

  system for asymmetric epoxidation was developed by using an achiral (salen)manganese(III) complex with chiral amine. Commercially available (-)-sparteine showed the highest asymmetric induction over the other chiral amines examined and addition of water to the reaction medium improved the induction up to 73% ee in the epoxidation of chromene derivative. Application of the system to the asymmetric oxidation

  通过使用非手性（salen）锰（III）与手性胺的配合物，开发了一种新的不对称环氧化催化剂体系。市售的（-）-天冬氨酸在所研究的其他手性胺上显示出最高的不对称诱导，向反应介质中加水可提高色烯衍生物的环氧化反应的诱导率，最高可达73％ee。还检查了该系统在甲基苯硫醚不对称氧化为其亚砜中的应用（至多25％ee）。这些结果支持了我们的建议，即Salen配体的非平面和手性结构在通过（salen）锰（III）络合物选择烯烃的对映体中起重要作用。
• Cruz-Almanza, Raymundo; Perez-Flores, Francisco; Brena, Leonardo, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 219 - 222
  作者：Cruz-Almanza, Raymundo、Perez-Flores, Francisco、Brena, Leonardo、Tapia, Eva、Ojeda, Reyna、Fuentes, Aidee

  DOI：——

  日期：——
• Efficient One-Pot Synthesis of 2,2-Dimethyl-2<i>H</i>-chromenes via Pd(II)-Catalyzed Coupling and SiO₂-Promoted Condensation of <i>o</i>-Halophenols with 2-Methyl-3-buten-2-ol
  作者：Jia Ti Tee、Marzieh Yaeghoobi、Chin Fei Chee、Noorsaadah Abd. Rahman

  DOI：10.1080/00397911.2015.1056371

  日期：2015.8.18

  An efficient synthesis of 2,2-dimethyl-2H-chromenes was accomplished by Pd(II)-catalyzed coupling and SiO2-promoted condensation of o-halophenols with 2-methyl-3-buten-2-ol (1,1-dimethylallyl alcohol) in one pot. The method is very general and can be useful for the synthesis of some natural 2,2-dimethyl-2H-chromenes.
• What is the origin of highly asymmetric induction by a chiral (salen)manganese(III) complex? Design of a conformationally fixed complex and its application to asymmetric epoxidation of 2, 2-dimethylchromenes
  作者：Yoshio N. Ito、Tsutomu Katsuki

  DOI：10.1016/s0040-4039(98)00763-1

  日期：1998.6

  The optically active (salen)manganese(III) complex 1 having a carboxylate group on the ethylenediamine moiety was found to be an efficient catalyst for the asymmetric epoxidation of several 2,2-dimethylchromene derivatives (up to 99% ee). A high level of turn-over number (up to 9, 200) was also achieved in this epoxidation. The pseudo-axially oriented carboxylate in 1 was postulated to coordinate to the manganese ion and to fix the conformation of the salen ligand in the form enantiomeric to that of normal chiral (salen)manganese(III) complexes. This was supported by the absolute configurations of the produced epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.