(2R,6R)-2-(3-bromopropyl)-1,7-dioxaspiro[5.5]undecane | 606942-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,6R)-2-(3-bromopropyl)-1,7-dioxaspiro[5.5]undecane
• CAS: 606942-38-5
• 化学式: C₁₂H₂₁BrO₂
• 分子量: 277.202
• InChiKey: CFPDVOGPJYFBBU-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,6-二甲氧基吲哚 、 (2R,6R)-2-(3-bromopropyl)-1,7-dioxaspiro[5.5]undecane 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 以75%的产率得到2-(3'-(4,6-dimethoxy-1H-indol-1-yl)prop-1-yl)-1,7-dioxaspiro[5.5]undecane
  参考文献：
  名称：

  Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015

  摘要：

  The naturally occurring phthalide-containing antibiotics spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108, have been reported to exhibit anti-H. pylori activity. However, the exact stereochemistry of spirolaxine methyl ether, CJ-12,954 or CJ-13,013, contributing to this observed activity has not been confirmed. The anti-H. pylori activity of several analogues of spirolaxine methyl ether, CJ-12,954 and CJ-13,013 of defined stereochemistry together with the anti-H. pylori activity of several indole analogues of the simpler phthalide-containing antibiotics CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015 is reported herein. A 1:1 mixture of spiroacetals 5b and 6b in which the phthalide substituent exhibited (3R)-stereochemistry was sixty times more active than the corresponding 1:1 mixture of spiroacetals with (3S)-stereochemistry. Notably, the unnatural (2 '' S)-diastereomer of spirolaxine methyl ether exhibited more potent anti-H. pylori activity than the natural product spirolaxine methyl ether. The 4,6-dimethoxyindoles 9, 10, 11 and 13 were all found to be less active than their parent compounds 1, 2, 3 and 4, respectively. Chain-shortened 4,6-dimethoxyindole analogue 12 of CJ-13,108 3 and 4,6-dimethoxyindole-spiroacetal 13 exhibited weak anti-H. pylori activity thus providing future opportunity for drug discovery programs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.037