2-(bromomethyl)-7-methoxynaphthalene | 103143-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(bromomethyl)-7-methoxynaphthalene
• CAS: 103143-23-3
• 化学式: C₁₂H₁₁BrO
• 分子量: 251.123
• InChiKey: OUUFWZKNTSSFAO-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  349.6±17.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险类别：
  6.1
• 危险性防范说明：
  P201,P202,P261,P264,P270,P271,P280,P302+P352,P304+P340,P308+P313,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331,H341
• 包装等级：
  III

反应信息

• 作为反应物：
  描述：

  2-(bromomethyl)-7-methoxynaphthalene 在 sodium hydroxide 、 氢氟酸 、 sodium ethanolate 作用下， 反应 109.75h， 生成 8-methoxy-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-one
  参考文献：
  名称：

  新的环戊[a]萘衍生物。合成2-（氨基甲酰基甲基）-8-羟基-3H-环戊[a]萘作为可能的脱氧核糖核酸粘合剂。

  摘要：

  通过在乙酸钠存在下用草酸二乙酯处理，将8-甲氧基-1-氧代-2,3-二氢-1H-环戊[a]萘（4）转化为草酰衍生物（7）。将钠盐形式的化合物7用溴乙酸乙酯在DMF中烷基化为2-（碳乙氧基甲基）-8-甲氧基-1-氧代-2,3-二氢-1H-环戊[a]萘（8）。用甲醇氨处理8，得到相应的酰胺（9）。8用48％HBr脱烷基并随后酯化，得到化合物10。10的氨解反应生成酰胺11，在还原并随后将还原的产物脱水后，得到所需的化合物2-（氨基甲酰基甲基）-8-羟基-3H-环戊[a]萘（2）。发现化合物2对培养物中的L1210和CCRF-CEM白血病细胞具有轻度生长抑制作用。根据热转变温度研究，

  DOI：

  10.1021/jm00179a008
• 作为产物：
  描述：

  (7-甲氧基萘-2-基)三氟甲磺酸酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 为溶剂， 反应 50.17h， 生成 2-(bromomethyl)-7-methoxynaphthalene
  参考文献：
  名称：

  A Rationally Designed Prototype of a Molecular Motor

  摘要：

  A proof of principle of the first rationally designed, chemically powered, molecular-scale motor is described. The thermodynamic considerations leading to the choice of 6a and 7a as the initial prototypes are provided, and the synthesis of 6a and 7a and the separation of them from their atropisomers are detailed. The phosgene-powered unidirectional rotation of 6a to its rotamer 6b is demonstrated. It is further established that shortening the length of the tether (-->7a) changes the rate-limiting step and accelerates the speed of rotation.

  DOI：

  10.1021/ja001048f

文献信息

• Cycloalkyl Lactam Derivatives As Inhibitors Of 11-Beta-Hydroxysteroid Dehydrogenase 1
  申请人：Aicher Thomas Daniel

  公开号：US20080214621A1

  公开（公告）日：2008-09-04

  The present invention provides compounds of formula I that are useful as potent and selective inhibitors of 11-beta hydroxysteroid dehydrogenase 1. The present invention further provides a pharmaceutical composition which comprises a compound of Formula I, or a pharmaceutical salt thereof, and a pharmaceutically acceptable carrier, diluent, or excipient. In addition, the present invention compositions containing these compounds for the treatment of metabolic syndrome, diabetes, hyperglycemia obesity, hypertension, hyperlipidemia, other symptoms associated with hyperglycemia, and related disorders. Formula I wherein G 1 is methylene or ethylene; L is —(C 1 -C 4 )alkylene-, —S—, —CH(OH)—, or —O—; R 0 is Formula II or Formula III and the other substituents are as defined in the claims.

  本发明提供了I式化合物，其作为11-β羟基类固醇脱氢酶1的有效且选择性抑制剂。本发明还提供了一种制药组合物，其包括I式化合物或其药物盐以及药学上可接受的载体、稀释剂或赋形剂。此外，本发明还提供了含有这些化合物的组合物，用于治疗代谢综合征、糖尿病、高血糖、肥胖症、高血压、高脂血症、与高血糖相关的其他症状和相关疾病。其中，式中G1为亚甲基或乙烯基；L为—(C1-C4)烷基、—S—、—CH(OH)—或—O—；R0为II式或III式，其他取代基在权利要求中定义。
• Synthesis and Insecticidal Activity of Spinosyns with C9-<i>O</i>-Benzyl Bioisosteres in Place of the 2′,3′,4′-Tri-<i>O</i>-methyl Rhamnose
  作者：M. Paige Oliver、Gary D. Crouse、David A. Demeter、Thomas C. Sparks

  DOI：10.1021/acs.jafc.5b01987

  日期：2015.6.17

  The spinosyns are fermentation-derived natural products active against a wide range of insect pests. They are structurally complex, consisting of two sugars (forosamine and rhamnose) coupled to a macrocyclic tetracycle. Removal of the rhamnose sugar results in a >100-fold reduction in insecticidal activity. C9-O-benzyl analogues of spinosyn D were synthesized to determine if the 2',3',4'-tri-O-methyl rhamnose moiety could be replaced with a simpler, synthetic bioisostere. Insecticidal activity was evaluated against larvae of Spodoptera exigua (beet arrayworm) and Helicoverpa zea (corn earworm). Whereas most analogues were far less active than spinosyn D, a few of the C9-O-benzyl analogues, such as 4-CN, 4-Cl, 2-isopropyl, and 3,5-diOMe, were within 3-15 times the activity of spinosyn D for larvae of S. exigua and H. zea. Thus, although not yet quite as effective, synthetic bioisosteres can substitute for the naturally occurring 2',3',4'-tri-O-methyl rhamnose moiety.
• Mukerjee, Y. N.; Gaur, S. P.; Jain, P. C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 985 - 987
  作者：Mukerjee, Y. N.、Gaur, S. P.、Jain, P. C.、Anand, Nitya

  DOI：——

  日期：——
• MUKERJEE Y. N.; GAUR S. P.; JAIN P. C. (LATE); ANAND NITYA, INDIAN J. CHEM., 24,(1985) N 9, 985-987
  作者：MUKERJEE Y. N.、 GAUR S. P.、 JAIN P. C. (LATE)、 ANAND NITYA

  DOI：——

  日期：——
• CYCLOALKYL LACTAM DERIVATIVES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE 1
  申请人：ELI LILLY AND COMPANY

  公开号：EP1830841B1

  公开（公告）日：2008-07-02