1-(6-methoxy-2-naphthyl)-2-methyl-propanol | 757230-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(6-methoxy-2-naphthyl)-2-methyl-propanol
• 英文别名: 1-(6-methoxy-[2]naphthyl)-2-methyl-propan-1-ol；1-(6-Methoxynaphthalen-2-yl)-2-methylpropan-1-ol
• CAS: 757230-69-6
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: SEOXNUVMCLWCMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-methoxy-2-naphthyl)-2-methyl-propanol 在 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-methoxy-6-(3-methylbut-1-en-2-yl)naphthalene
  参考文献：
  名称：

  三取代甲烷和手性叔α-羟醛（四取代甲烷的可能中间体）的合成方法†

  摘要：

  据报道，一系列含有芳基和杂芳基环的三取代甲烷，以及在中心甲烷碳和苯环之间的硫间隔基。在一种具有高对映选择性的不对称四取代甲烷的方法中，通过在二取代烯烃上进行无尖锐的二羟基化反应，然后对伯醇进行化学选择性氧化，合成了手性叔α-羟基醛。

  DOI：

  10.1039/c3ra41826j
• 作为产物：
  描述：

  (6-methoxy-2-naphthyl) isopropyl ketone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以70%的产率得到1-(6-methoxy-2-naphthyl)-2-methyl-propanol
  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

文献信息

• Horeau; Ormancey, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1953, vol. 236, p. 826
  作者：Horeau、Ormancey

  DOI：——

  日期：——
• C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors
  作者：Nobuyuki Matsunaga、Tomohiro Kaku、Akio Ojida、Toshimasa Tanaka、Takahito Hara、Masuo Yamaoka、Masami Kusaka、Akihiro Tasaka

  DOI：10.1016/j.bmc.2004.06.016

  日期：2004.8

  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.
• Synthetic approach towards trisubstituted methanes and a chiral tertiary α-hydroxyaldehyde, a possible intermediate for tetrasubstituted methanes
  作者：Priyanka Singh、Subal Kumar Dinda、Shagufta、Gautam Panda

  DOI：10.1039/c3ra41826j

  日期：——

  spacer between the central methano-carbon and benzene ring, is reported. In an approach towards asymmetric tetrasubstituted methane with high enantioselectivity, chiral tertiary α-hydroxyaldehyde has been synthesized through a Sharpless dihydroxylation on a disubstituted olefin, followed by the chemoselective oxidation of the primary alcohol.

  据报道，一系列含有芳基和杂芳基环的三取代甲烷，以及在中心甲烷碳和苯环之间的硫间隔基。在一种具有高对映选择性的不对称四取代甲烷的方法中，通过在二取代烯烃上进行无尖锐的二羟基化反应，然后对伯醇进行化学选择性氧化，合成了手性叔α-羟基醛。