7-methoxymurrayacine | 132160-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-methoxymurrayacine
• 英文别名: 9-methoxy-3,3-dimethyl-11H-pyrano[3,2-a]carbazole-5-carbaldehyde
• CAS: 132160-51-1
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: ULTYRPCVVWZHPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-methylmurrayamine A 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.5h， 以93%的产率得到7-methoxymurrayacine
  参考文献：
  名称：

  高效的铁介导方法制备吡喃并[3,2 - a ]咔唑生物碱—首次合成O-甲基Murrayamine A和7-甲氧基Murrayacine，首次不对称合成并确定（-）-反式-dihydroxygirinimbine的绝对构型† ‡

  摘要：

  铁介导的氧化环化提供了一种有效的方法 吡喃并[3,2- a ]咔唑生物碱。因此，改进了通往吉利比滨报道了尿嘧啶和O-甲基尿嘧啶A和7-甲氧基尿嘧啶的第一批总合成。的不对称环氧化吉利比滨导致了（-）-反式-二羟基基里尼宁及其绝对构型的赋值。

  DOI：

  10.1039/c0ob01088j

文献信息

• Synthesis of Prenyl- and Geranyl-Substituted Carbazole Alkaloids by DIBAL-H Promoted Reductive Pyran Ring Opening of Dialkylpyrano[3,2-<i>a</i>]carbazoles
  作者：Ronny Hesse、Olga Kataeva、Arndt W. Schmidt、Hans-Joachim Knölker

  DOI：10.1002/chem.201403645

  日期：2014.7.28

  The DIBAL‐H promoted reductive pyran ring opening of dialkylpyrano[3,2‐a]carbazoles provides a direct access to a broad range of prenyl‐ and geranyl‐substituted carbazoles. Formation of a pyran ring followed by reductive ring opening represents a new method for the introduction of prenyl and geranyl groups. In the course of the present work, we achieved the first total syntheses of the following eight

  DIBAL-H促进了二烷基吡喃并[3,2- a ]咔唑的还原吡喃环的打开，可直接使用各种异戊二烯基和香叶基取代的咔唑。吡喃环的形成然后还原性开环代表了引入异戊二烯基和香叶基的新方法。在目前的工作过程中，我们完成了以下八种咔唑生物碱的首次合成：clauraila-E，7-羟基庚茶碱，7-甲氧基庚茶碱，mukoenine-B（clausenatine-A），mukoenine-A（girinimbilol），mahanimbinol （马哈宁比洛），欧司他汀-A和异莫拉利福林-B.
• Total synthesis and neuroprotective effect of O-methylmurrayamine A and 7-methoxymurrayacine
  作者：Ying-Da Zang、Chuang-Jun Li、Xiu-Yun Song、Jie Ma、Jing-Zhi Yang、Nai-Hong Chen、Dong-Ming Zhang

  DOI：10.1080/10286020.2017.1327952

  日期：2017.6.3

  O-Methylmurrayamine A (7) and 7-methoxymurrayacine (8) are natural products isolated from Murraya koenigii and Murraya siamensis, respectively. In this paper, we report the synthesis of 7 and 8 which are featured in the key step of cyclization to form carbazole intermediate 5 with mild conditions. The structures were confirmed by H-1 NMR, C-13 NMR, and HR-ESI-MS. In addition, compounds 7 and 8 were tested for their neuroprotective effects against H2O2 -induced PC12 cell damage. The results showed that compounds 7 and 8 have neuroprotective effect.
• Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids—first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (−)-trans-dihydroxygirinimbine
  作者：Konstanze K. Gruner、Thomas Hopfmann、Kazuhiro Matsumoto、Anne Jäger、Tsutomu Katsuki、Hans-Joachim Knölker

  DOI：10.1039/c0ob01088j

  日期：——

  Iron-mediated oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reported. Asymmetric epoxidation of girinimbine led to (−)-trans-dihydroxygirinimbine and the assignment of its absolute configuration.

  铁介导的氧化环化提供了一种有效的方法 吡喃并[3,2- a ]咔唑生物碱。因此，改进了通往吉利比滨报道了尿嘧啶和O-甲基尿嘧啶A和7-甲氧基尿嘧啶的第一批总合成。的不对称环氧化吉利比滨导致了（-）-反式-二羟基基里尼宁及其绝对构型的赋值。