1-[4-Hydroxy-3-(hydroxymethyl)-2-methoxy-5-(2-methylpropyl)phenyl]-1-pentanone | 798559-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-Hydroxy-3-(hydroxymethyl)-2-methoxy-5-(2-methylpropyl)phenyl]-1-pentanone
• 英文别名: 1-[4-hydroxy-3-(hydroxymethyl)-2-methoxy-5-(2-methylpropyl)phenyl]pentan-1-one
• CAS: 798559-89-4
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: ZOISTHUVVDVVLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-Hydroxy-3-(hydroxymethyl)-2-methoxy-5-(2-methylpropyl)phenyl]-1-pentanone 在 manganese(IV) oxide 、 四氧化锇 、 三正丁胺 、 四氯化钛 、 N-甲基吗啉氧化物 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 生成
  参考文献：
  名称：

  Studies Toward the Synthesis of Luminacin D:  Assembly of Simplified Analogues Devoid of the Epoxide Displaying Antiangiogenic Activity

  摘要：

  [GRAPHICS]A series of structurally simplified luminacin analogues devoid of the epoxide ring are assembled in a stereocontrolled manner from 2,4-dimethoxybenzaldehyde using a syn-selective aldol reaction as the key step. The success of the approach is critically dependent on the nature and extent of the alcohol protecting groups. The synthetic analogues inhibit VEGF-stimulated angiogenesis in an in vitro assay indicating that the epoxide is not essential for biological activity in this compound class.

  DOI：

  10.1021/ol048462v
• 作为产物：
  描述：

  1-[2,4-Dihydroxy-5-(2-methylpropyl)phenyl]-1-pentanone 在 盐酸 、 氢氧化钾 、 potassium carbonate 、 对甲苯磺酸 、 calcium chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 146.0h， 生成 1-[4-Hydroxy-3-(hydroxymethyl)-2-methoxy-5-(2-methylpropyl)phenyl]-1-pentanone
  参考文献：
  名称：

  Studies Toward the Synthesis of Luminacin D:  Assembly of Simplified Analogues Devoid of the Epoxide Displaying Antiangiogenic Activity

  摘要：

  [GRAPHICS]A series of structurally simplified luminacin analogues devoid of the epoxide ring are assembled in a stereocontrolled manner from 2,4-dimethoxybenzaldehyde using a syn-selective aldol reaction as the key step. The success of the approach is critically dependent on the nature and extent of the alcohol protecting groups. The synthetic analogues inhibit VEGF-stimulated angiogenesis in an in vitro assay indicating that the epoxide is not essential for biological activity in this compound class.

  DOI：

  10.1021/ol048462v

文献信息

• Total synthesis of (±)-luminacin D
  作者：Daniel Oehlrich、Sandrine M.E. Vidot、Mark W. Davies、Guy J. Clarkson、Michael Shipman

  DOI：10.1016/j.tet.2007.03.096

  日期：2007.5

  A 15-step synthesis of (+/-)-luminacin D from ethyl pent-2-ynoate is reported. The pivotal step involves the formation of the central C-2'/C-3' bond of the natural product by condensation of the titanium enolate derived from aromatic ketone 1 with aldehyde 2a. A remote asymmetric centre in aldehyde 2a exerts control over the stereochemical course of this reaction, with the major adduct (3a, 54% yield) possessing the required (2'S*,3'R*,5R*)-stereochemistry. This assignment was unambiguously established by X-ray crystallography of late stage synthetic intermediate, 17. Further manipulation of 3a (six steps) yielded synthetic ()-luminacin D spectroscopically identical to material isolated from Streptomyces sp. Mer-VD1207 by Naruse et al. (C) 2007 Elsevier Ltd. All rights reserved.
• Studies Toward the Synthesis of Luminacin D:  Assembly of Simplified Analogues Devoid of the Epoxide Displaying Antiangiogenic Activity
  作者：Mark W. Davies、Lesley Maskell、Michael Shipman、Alexandra M. Z. Slawin、Sandrine M. E. Vidot、Jacqueline L. Whatmore

  DOI：10.1021/ol048462v

  日期：2004.10.1

  [GRAPHICS]A series of structurally simplified luminacin analogues devoid of the epoxide ring are assembled in a stereocontrolled manner from 2,4-dimethoxybenzaldehyde using a syn-selective aldol reaction as the key step. The success of the approach is critically dependent on the nature and extent of the alcohol protecting groups. The synthetic analogues inhibit VEGF-stimulated angiogenesis in an in vitro assay indicating that the epoxide is not essential for biological activity in this compound class.