(6-isopropoxy-2-naphthyl)methanol | 757230-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (6-isopropoxy-2-naphthyl)methanol
• 英文别名: (6-propan-2-yloxynaphthalen-2-yl)methanol
• CAS: 757230-58-3
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: KHNFJDRXIIMMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (6-isopropoxy-2-naphthyl)methanol 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  通过镍催化醚脱氧形成碳-碳键

  摘要：

  在这篇文章中，开发了一个成功的协议，通过在还原剂的存在下通过镍催化挤出醚的 O 原子来构建碳 - 碳键。该方法是通过具有良好官能团耐受性的醚的双 CO 活化来构建 sp3-sp3 CC 键的高度经济途径。

  DOI：

  10.1021/jacs.7b02326
• 作为产物：
  描述：

  6-isopropoxy-2-naphthaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以63%的产率得到(6-isopropoxy-2-naphthyl)methanol
  参考文献：
  名称：

  C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors

  摘要：

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.016