4-{2-[(4aS,9aS)-1-But-3-ynyl-5-methoxy-4a-(3-methoxy-phenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridin-3-yl]-4-methoxy-phenyl}-3-methoxy-pyran-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-{2-[(4aS,9aS)-1-But-3-ynyl-5-methoxy-4a-(3-methoxy-phenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridin-3-yl]-4-methoxy-phenyl}-3-methoxy-pyran-2-one
• 英文别名: 4-[2-[(4aS,9aS)-1-but-3-ynyl-5-methoxy-4a-(3-methoxyphenyl)-9,9a-dihydro-2H-indeno[2,1-b]pyridin-3-yl]-4-methoxyphenyl]-3-methoxypyran-2-one
• 化学式: C₃₇H₃₅NO₆
• 分子量: 589.688
• InChiKey: HCMRGNNUNLAHKY-DYKQPOOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{2-[(4aS,9aS)-1-But-3-ynyl-5-methoxy-4a-(3-methoxy-phenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridin-3-yl]-4-methoxy-phenyl}-3-methoxy-pyran-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis of (±)-Haouamine A

  摘要：

  The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.

  DOI：

  10.1021/ja0602997
• 作为产物：
  描述：

  (3-methoxyphenyl)magnesium bromide 在 N,N-二甲基丙烯基脲 、 indium 、 sodium tetrahydroborate 、 四氧化锇 、 四(三苯基膦)钯 、 四溴环己二烯-1-酮 、 盐酸羟胺 、 sodium acetate 、 六甲基二锡 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 氯化铵 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 67.0h， 生成 4-{2-[(4aS,9aS)-1-But-3-ynyl-5-methoxy-4a-(3-methoxy-phenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridin-3-yl]-4-methoxy-phenyl}-3-methoxy-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (±)-Haouamine A

  摘要：

  The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.

  DOI：

  10.1021/ja0602997

文献信息

• Formal total synthesis of (−)-haouamine A
  作者：Alois Fürstner、Jens Ackerstaff

  DOI：10.1039/b805295f

  日期：——

  A largely catalysis based approach to optically active haouamine A (−)-1 is presented, which provides the hexacyclic compound 25 previously used to construct this cytotoxic marine alkaloid.

  本文介绍了一种基于催化作用的光活性吡咯里西啶生物碱(-1)的合成方法，该方法提供了先前用于构建这种细胞毒性海洋生物碱的六环化合物25。
• Total Synthesis of (±)-Haouamine A
  作者：Phil S. Baran、Noah Z. Burns

  DOI：10.1021/ja0602997

  日期：2006.3.1

  The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.