(+)-buphanisine | 124093-57-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: (+)-buphanisine
• 英文别名: vittatine；(1R,13S,15S)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraene
• CAS: 124093-57-8
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: HATSAIPBKRRCME-DQYPLSBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl (3aR,6S,7aS)-3a-(1,3-benzodioxol-5-yl)-6-methoxy-3,6,7,7a-tetrahydro-2H-indole-1-carboxylate 在 三氟乙酸 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 11.08h， 生成 (+)-buphanisine
  参考文献：
  名称：

  Enantioselective Synthesis ofAmaryllidaceaeAlkaloids (+)-Vittatine, (+)-epi-Vittatine, and (+)-Buphanisine

  摘要：

  Cat. on a hot tin roof: Enantioselective catalytic Michael addition of α-cyanoketones to acrylates under bifunctional organocatalysis was used to construct the unique arylic all-carbon quaternary stereocenter, which is synthetically crucial in the chemical synthesis of optically pure cis-aryl hydroindole alkaloids. The protocol offers an asymmetric route to (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine.

  DOI：

  10.1002/asia.201300595

文献信息

• Total syntheses of (±)-crinine and (±)-buphanisine
  作者：Stephen F Martin、Carlton L Campbell

  DOI：10.1016/s0040-4039(00)95766-6

  日期：1987.1

  The concise total syntheses of the alkaloids (±)-crinine (1) and (±)-buphanisine (2) have been completed by a strategy that features the application of a general procedure for the elaboration of a quaternary carbon at a carbonyl center for construction of the key intermediate 4,4-disubstituted cyclohexenone 7.

  简明的总生物碱（±）-可瑞宁（1）和（±）-布芬尼辛（2）的总合成已通过一种策略完成，该策略的特点是应用了在羰基中心修饰季碳的通用程序关键中间体4,4-二取代的环己烯酮的构建7。
• Total syntheses of crinine and related alkaloids
  作者：Claire Bru、Catherine Guillou

  DOI：10.1016/j.tet.2006.07.005

  日期：2006.9

  Cyclizations of a bicyclic amine via an intramolecular Heck reaction followed by an oxidation reaction generated a tetracyclic spirocyclohexadione. From this useful intermediate, different crinine alkaloids such as crinine, buphanisine, flexinine, and augustine could be synthesized. Dienol/benzene or dienone/phenol rearrangement of this tetracyclic spirodienone afforded apogalanthamine analogs.

  通过分子内的Heck反应，然后通过氧化反应，使双环胺环化，生成四环螺环己二酮。从这种有用的中间体中，可以合成不同的克林宁生物碱，例如克林宁，布芬尼辛，福西宁和奥古斯丁。该四环螺二烯酮的二烯酚/苯或二烯酮/苯酚重排提供了阿朴加兰他敏类似物。
• Enantioselective Synthesis of<i>Amaryllidaceae</i>Alkaloids (+)-Vittatine, (+)-<i>epi</i>-Vittatine, and (+)-Buphanisine
  作者：Meng-Xue Wei、Cheng-Tao Wang、Ji-Yuan Du、Hu Qu、Pei-Rong Yin、Xu Bao、Xiao-Yan Ma、Xian-He Zhao、Guo-Biao Zhang、Chun-An Fan

  DOI：10.1002/asia.201300595

  日期：2013.9

  Cat. on a hot tin roof: Enantioselective catalytic Michael addition of α-cyanoketones to acrylates under bifunctional organocatalysis was used to construct the unique arylic all-carbon quaternary stereocenter, which is synthetically crucial in the chemical synthesis of optically pure cis-aryl hydroindole alkaloids. The protocol offers an asymmetric route to (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine.