(1S,2R)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydroindene-1,2-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2R)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydroindene-1,2-diol
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: GHXAPGZKFGFNTM-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydroindene-1,2-diol 在 N,N-二甲基丙烯基脲 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 8.0h， 生成 1-[2-(2-Bromo-5-methoxy-phenyl)-allyl]-7-methoxy-1-(3-methoxy-phenyl)-indan-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
• 作为产物：
  描述：

  (3-methoxyphenyl)magnesium bromide 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 9.5h， 生成 (1S,2R)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydroindene-1,2-diol
  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

• Total synthesis of haouamine A: the indeno-tetrahydropyridine core
  作者：Noah Z. Burns、Mikkel Jessing、Phil S. Baran

  DOI：10.1016/j.tet.2009.05.075

  日期：2009.8

  A full account of synthetic efforts toward the indeno-tetrahydropyridine core of haouamine A is presented. initial failed strategies led to the unexpected discovery of a mild abnormal Chichibabin pyridine synthesis and provided knowledge and inspiration for the development of a cascade annulation that has enabled rapid and scalable access to the core in either racemic or enantiopure form. (C) 2009 Elsevier Ltd. All rights reserved.
• On the Origin of the Haouamine Alkaloids
  作者：Noah Z. Burns、Phil S. Baran

  DOI：10.1002/anie.200704576

  日期：2008.1
• 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.