2-hydroxymethyl-3-methylnaphthalene | 31554-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxymethyl-3-methylnaphthalene
• 英文别名: 3-methyl-2-naphthylmethyl alcohol；(3-methylnaphthalen-2-yl)methanol；2-Hydroxymethyl-3-methylnaphthalin；2-Methyl-3-hydroxymethyl-naphthalin；3-methyl-2-hydroxymethylnaphthalene；3-Methyl-2-naphthalenemethanol
• CAS: 31554-16-2
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: DOZSTMNNHWFGOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-3-methylnaphthalene 在 氯化亚砜 、 盐酸羟胺 、 sodium methylate 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 21.17h， 生成
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006
• 作为产物：
  描述：

  2-<(Dimethylamino)methyl>-3-methylnaphthalene 在 氢氧化钾 作用下， 生成 2-hydroxymethyl-3-methylnaphthalene
  参考文献：
  名称：

  摘要：

  The example of the rearrangement-cleavage under the action of 25% aqueous potassium hydroxide at 90-92degreesC of ammonium salts containing both 3-methyl-2-naphthylmethyl and 2-bromoethyl, allyl, 4 methallyl, 2-bromoallyl, 3-phenylallyl, 2-propynyl, or 3-phenylphenyl-2-propynyl groups was used to show that the reaction always involves the aromatic ring of the 3-methyl-2-naphthylmethyl group. Along with rearrangement-cleavage, nucleophilic substitution of the 2-naphthylmethyl group takes place.

  DOI：

  10.1023/a:1026365104706

文献信息

• Novel naphthalenyl-3H-1,2,3,5-oxathiadiazole 2-oxides useful as
  申请人：American Home Products Corporation

  公开号：US04895861A1

  公开（公告）日：1990-01-23

  This invention relates to novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides, processes for their preparation, to methods for using the compounds, and to pharmaceutical preparations thereof. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  这项发明涉及新型取代的3H-1,2,3,5-噁硫二唑-2-氧化物，其制备方法，以及使用这些化合物的方法，以及其药物制剂。这些化合物具有药理特性，使它们对于治疗糖尿病及相关疾病有益。
• Novel naphthalenylalkyl-3H-1,2,3,5-oxathiadiazole 2-oxides useful as
  申请人：American Home Products Corporation

  公开号：US04897405A1

  公开（公告）日：1990-01-30

  This invention relates to novel [(substituted naphthalenyl)alkyl]-3H-1,2,3,5-oxathiadiazole 2-oxides, to the processes for their preparation, to methods for using the compounds, and to pharmaceutical compositions thereof. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  这项发明涉及新型[(取代萘基)烷基]-3H-1,2,3,5-噻二唑二氧化物，以及它们的制备方法、化合物的使用方法和相关的药物组合物。这些化合物具有药理特性，使它们对于治疗糖尿病及相关疾病有益。
• An Improvement of the Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Carbonates with Alkenes
  作者：Ryoichi Kuwano、Yushu Jin、Kentaro Ishizuka

  DOI：10.1055/s-0034-1379014

  日期：——

  complex, which is generated in situ from Pd(η 3-C3H5)Cp and tris(4-methoxy-3,5-dimethylphenyl)phosphine, catalyzed the [4+2] cycloaddition of o-(silylmethyl)benzyl carbonates with alkenes. The reaction of the benzyl esters with methyl crotonate gave methyl 3-methyltetralin-2-carboxylate in 84% yield with 2% catalyst loading.

  钯配合物由 Pd(η 3-C3H5)Cp 和三（4-甲氧基-3,5-二甲基苯基）膦原位生成，催化邻（甲硅烷基甲基）苄基碳酸酯与烯烃。苄酯与巴豆酸甲酯的反应以84%的收率和2%的催化剂负载得到3-甲基四氢化萘-2-羧酸甲酯。
• LACTAM-CONTAINING COMPOUNDS AND DERIVATIVES THEREOF AS FACTOR XA INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：US20170050964A1

  公开（公告）日：2017-02-23

  The present application describes lactam-containing compounds and derivatives thereof of Formula I: P 4 —P-M-M 4 I or pharmaceutically acceptable salt forms thereof, wherein ring P, if present is a 5-7 membered carbocycle or heterocycle and ring M is a 5-7 membered carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I中含有内酰胺的化合物及其衍生物：P4—P-M-M4I或其药用盐形式，其中环P（如果存在）是一个5-7成员的碳环或杂环，环M是一个5-7成员的碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是因子Xa。
• Diastereoselective Synthesis of CF₃-Substituted Spiroisochromans by [1,5]-Hydride Shift/Cyclization/Intramolecular Friedel–Crafts Reaction Sequence
  作者：Risa Tamura、Eriko Kitamura、Ryosuke Tsutsumi、Masahiro Yamanaka、Takahiko Akiyama、Keiji Mori

  DOI：10.1021/acs.orglett.9b00668

  日期：2019.4.5

  Developed herein is a diastereoselective synthesis of CF3-substituted spiroisochromans via C(sp3)–H bond functionalization involving sequential transformations ([1,5]-hydride shift/cyclization/elimination of MeOH/intramolecular Friedel–Crafts reaction).

  本文开发的是通过C（sp 3）-H键官能化涉及顺序转换（[[1,5]-氢化物转移/环化/消除MeOH /分子内Friedel-Crafts反应）的CF 3取代的螺二硫代非对映异构体的非对映选择性合成。