4,4'-(2-苯基丁-1-烯-1,1-二基)二苯酚 | 71461-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 4,4'-(2-苯基丁-1-烯-1,1-二基)二苯酚
• 英文名称: (-)-ephedradine A
• 英文别名: orantine；Orantin；Ephedradin A；Ephedradine A；(11S,17R,18R)-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetrazatetracyclo[9.8.6.212,15.014,18]heptacosa-12,14,26-triene-19,24-dione
• CAS: 71461-13-7
• 化学式: C₂₈H₃₆N₄O₄
• 分子量: 492.618
• InChiKey: ASCIWXOCZAWSON-RNJDCESWSA-N

物化性质

• 沸点：
  746.1±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  36
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-(2-苯基丁-1-烯-1,1-二基)二苯酚 在 溴 作用下， 生成 (1S,18²R,18³R)-18²-(3,5-dibromo-4-hydroxy-phenyl)-18^2,3-dihydro-2,6,11,15-tetraaza-18(5,3)-benzofurana-bicyclo[9.6.2]nonadecaphane-16,19-dione
  参考文献：
  名称：

  Structure of ephedradine A, a hypotensive principle of Ephedra roots

  摘要：

  DOI：

  10.1016/s0040-4039(01)93575-0
• 作为产物：
  描述：

  (-)-(S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 在 聚合甲醛 、 hemin 、 双氧水 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.17h， 生成 4,4'-(2-苯基丁-1-烯-1,1-二基)二苯酚
  参考文献：
  名称：

  Biomimetic Formation of Macrocyclic Spermine Alkaloids

  摘要：

  Dihydroxyverbacine (10), a precursor for oxidative phenol coupling. was obtained via (+/-)-buchnerine (14). whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine (1). orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.

  DOI：

  10.1002/1522-2675(20010711)84:7<2108::aid-hlca2108>3.0.co;2-g

文献信息

• Stereocontrolled Total Synthesis of (−)-Ephedradine A (Orantine)
  作者：Wataru Kurosawa、Toshiyuki Kan、Tohru Fukuyama

  DOI：10.1021/ja036011k

  日期：2003.7.1

  The stereocontrolled total synthesis of (-)-ephedradine A has been accomplished. The synthesis features an asymmetric C-H insertion reaction, an intramolecular ester-amide exchange reaction, and a Sharpless asymmetric aminohydroxylation reaction. Construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction.

  (-)-麻黄碱A的立体控制全合成已完成。该合成具有不对称 CH 插入反应、分子内酯-酰胺交换反应和 Sharpless 不对称氨基羟基化反应。复杂大环的构建通过Ns-strategy和分子内aza-Wittig反应进行。
• Total synthesis of (−)-ephedradine A: an efficient construction of optically active dihydrobenzofuran-ring via C–H insertion reaction
  作者：Wataru Kurosawa、Hideki Kobayashi、Toshiyuki Kan、Tohru Fukuyama

  DOI：10.1016/j.tet.2004.06.144

  日期：2004.10

  The stereocontrolled total synthesis of (−)-ephedradine A (1) has been accomplished. Construction of optically active dihydrobenzofuran-ring was performed by a novel asymmetric C–H insertion reaction. After an intramolecular ester–amide exchange reaction and a Sharpless asymmetric aminohydroxylation reaction, construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular

  （-）-麻黄碱A（1）的立体控制全合成已完成。光学活性的二氢苯并呋喃环的构建是通过新型的不对称C–H插入反应进行的。在分子内酯-酰胺交换反应和Sharpless不对称氨基羟基化反应之后，通过Ns-策略和分子内aza-Wittig反应进行复杂大环的构建。
• Die absolute Konfiguration des Spermin-Alkaloides Aphelandrin
  作者：Armin Guggisberg、Roland Prewo、Manfred Hesse

  DOI：10.1002/hlca.19860690508

  日期：1986.7.30

  The Absolute Configuration of the Spermine Alkaloid Aphelandrine

  精胺生物碱麻黄碱的绝对构型
• Biomimetic Formation of Macrocyclic Spermine Alkaloids
  作者：Vladimir Dimitrov、Hervé Geneste、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/1522-2675(20010711)84:7<2108::aid-hlca2108>3.0.co;2-g

  日期：2001.7.11

  Dihydroxyverbacine (10), a precursor for oxidative phenol coupling. was obtained via (+/-)-buchnerine (14). whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine (1). orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.
• Structure of ephedradine A, a hypotensive principle of Ephedra roots
  作者：Mitsuru Tamada、Katsuya Endo、Hiroshi Hikino、Chizuko Kabuto

  DOI：10.1016/s0040-4039(01)93575-0

  日期：1979.1