tert-butyl 6-(hydroxymethyl)-2-naphthylcarbamate | 372149-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 6-(hydroxymethyl)-2-naphthylcarbamate
• 英文别名: tert-butyl N-[6-(hydroxymethyl)naphthalen-2-yl]carbamate
• CAS: 372149-43-4
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: WMPBUPBWTKINSR-UHFFFAOYSA-N

物化性质

• 沸点：
  407.3±20.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-(hydroxymethyl)-2-naphthylcarbamate 在 manganese dioxide 异丙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以to obtain tert-butyl 6-formyl-2-naphthylcarbamate (889 mg) as a white powder的产率得到tert-butyl 6-formylnaphthalen-2-ylcarbamate
  参考文献：
  名称：

  Melanin-concentrating hormone antagonist

  摘要：

  一种黑色素浓集激素拮抗剂，包括式(I)的化合物：其中Ar1是可以被取代的环状基团；X和Y相同或不同，是具有1至6个原子的主链间隔基团；Ar是可以被取代的紧凑多环芳香环；R1和R2相同或不同，是氢原子或可以被取代的碳氢基团；或者R1和R2，与相邻的氮原子一起，可以形成可以被取代的含氮杂环；或者R2，与相邻的氮原子和Y一起，可以形成可以被取代的含氮杂环；或者R2，与相邻的氮原子、Y和Ar一起，可以形成紧凑环；或其盐，可用作预防或治疗肥胖症等的药物。

  公开号：

  US06930185B2
• 作为产物：
  描述：

  2,6-萘二羧酸二甲酯 在 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 tert-butyl 6-(hydroxymethyl)-2-naphthylcarbamate
  参考文献：
  名称：

  Melanin-Concentrating Hormone Receptor 1 Antagonists. Synthesis and Structure–Activity Relationships of Novel 3-(Aminomethyl)quinolines

  摘要：

  It was found that 3-(aminomethyl)quinoline derivatives showed high binding affinities for melanin-concentrating hormone receptor 1 (MCHR1) with reduced affinity for serotonin receptor 2c (5-HT2c) when the dihydronaphthalene nucleus of compound 1 (human MCHR1, IC50 = 1.9 nM; human 5-HT2c receptor, IC50 = 0.53 nM) was replaced by other bicyclic core scaffolds. Among the synthesized compounds, 8-methylquinoline derivative 5v especially showed high binding affinity (IC50 = 0.54 nM), potent in vitro antagonistic activity (IC50 = 2.8 nM) for MCHR1, and negligible affinity for 5-HT2c receptor (IC50 > 1000 nM). Oral administration of 5v significantly and dose-dependently suppressed nocturnal food intake in diet-induced obese rats and did not affect food intake in MCHR1-deficient mice. These results and rat pharmacokinetic study findings suggested that compound 5v is a highly potent, orally bioavailable, and centrally acting nonpeptide MCHR1 antagonist.

  DOI：

  10.1021/jm201596h

文献信息

• Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis
  作者：Zhi-Chao Cao、Da-Gang Yu、Ru-Yi Zhu、Jiang-Bo Wei、Zhang-Jie Shi

  DOI：10.1039/c4cc10084k

  日期：——

  A direct arylation to furnish diarylmethanes from benzyl alcohols was realized through Pd(PPh₃)₄-catalyzed Suzuki–Miyaura coupling via benzylic C–O activation in the absence of any additives. The arylation is compatible with various functional groups. This development provides an atom- and step-economic way to approach a diarylmethane scaffold under mild and environmentally benign conditions.

  通过Pd(PPh3)4催化的Suzuki–Miyaura偶联反应，利用苯甲醇直接芳基化制备二芳基甲烷，通过对苄基C–O活化，无需任何添加剂。这种芳基化反应与多种官能团兼容。该研究开发了一种原子经济、步骤经济的方法，在温和环保的条件下制备二芳基甲烷骨架。
• MELANIN CONCENTRATING HORMONE ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1285651B1

  公开（公告）日：2010-09-01
• US6930185B2
  申请人：——

  公开号：US6930185B2

  公开（公告）日：2005-08-16
• Melanin-Concentrating Hormone Receptor 1 Antagonists. Synthesis and Structure–Activity Relationships of Novel 3-(Aminomethyl)quinolines
  作者：Makoto Kamata、Toshiro Yamashita、Toshihiro Imaeda、Toshio Tanaka、Shinichi Masada、Masahiro Kamaura、Shizuo Kasai、Ryoma Hara、Shigekazu Sasaki、Shiro Takekawa、Asano Asami、Tomoko Kaisho、Nobuhiro Suzuki、Shuntaro Ashina、Hitomi Ogino、Yoshihide Nakano、Yasutaka Nagisa、Koki Kato、Kaneyoshi Kato、Yuji Ishihara

  DOI：10.1021/jm201596h

  日期：2012.3.8

  It was found that 3-(aminomethyl)quinoline derivatives showed high binding affinities for melanin-concentrating hormone receptor 1 (MCHR1) with reduced affinity for serotonin receptor 2c (5-HT2c) when the dihydronaphthalene nucleus of compound 1 (human MCHR1, IC50 = 1.9 nM; human 5-HT2c receptor, IC50 = 0.53 nM) was replaced by other bicyclic core scaffolds. Among the synthesized compounds, 8-methylquinoline derivative 5v especially showed high binding affinity (IC50 = 0.54 nM), potent in vitro antagonistic activity (IC50 = 2.8 nM) for MCHR1, and negligible affinity for 5-HT2c receptor (IC50 > 1000 nM). Oral administration of 5v significantly and dose-dependently suppressed nocturnal food intake in diet-induced obese rats and did not affect food intake in MCHR1-deficient mice. These results and rat pharmacokinetic study findings suggested that compound 5v is a highly potent, orally bioavailable, and centrally acting nonpeptide MCHR1 antagonist.
• Melanin-concentrating hormone antagonist
  申请人：——

  公开号：US20040077628A1

  公开（公告）日：2004-04-22

  A melanin-concentrating hormone antagonist comprising a compound of the formula (I): 1 wherein Ar 1 is a cyclic group which may be substituted; X and Y are the same or different and are a spacer having a main chain of 1 to 6 atoms; Ar is a condensed polycyclic aromatic ring which may be substituted; R 1 and R 2 are the same or different and are hydrogen atom or a hydrocarbon group which may be substituted; or R 1 and R 2 , together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic ring which may be substituted; or R 2 , together with the adjacent nitrogen atom and Y, may form a nitrogen-containing heterocyclic ring which may be substituted; or R 2 , together with the adjacent nitrogen atom, Y and Ar, may form a condensed ring; or a salt thereof is useful as an agent for preventing or treating obesity, etc.

  一种黑色素浓集激素拮抗剂，包括化合物(I)的一种，其中Ar1是一个可以被取代的环状基团；X和Y相同或不同，是具有1至6个原子的主链间隔物；Ar是一个可以被取代的紧凑多环芳香环；R1和R2相同或不同，是氢原子或可以被取代的碳氢基团；或者R1和R2与相邻的氮原子一起可以形成一个可以被取代的含氮杂环；或者R2与相邻的氮原子和Y一起可以形成一个可以被取代的含氮杂环；或者R2与相邻的氮原子、Y和Ar一起可以形成一个紧凑环；或其盐，可用作预防或治疗肥胖等药物。