1-Bromo-3-(3-nonynyloxymethyl)benzene | 152123-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Bromo-3-(3-nonynyloxymethyl)benzene
• 英文别名: 1-bromo-3-(non-3-ynoxymethyl)benzene
• CAS: 152123-77-8
• 化学式: C₁₆H₂₁BrO
• 分子量: 309.246
• InChiKey: WRWRCXHBBBUNRE-UHFFFAOYSA-N

物化性质

• 沸点：
  372.9±27.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Bromo-3-(3-nonynyloxymethyl)benzene 在 sodium hydroxide 、 四(三苯基膦)钯 、 N,N-二甲基乙酰胺 、 铜 、 锌 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 3-(3-Non-3-ynyloxymethyl-phenyl)-propionic acid
  参考文献：
  名称：

  (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases

  摘要：

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.

  DOI：

  10.1021/jm9606047
• 作为产物：
  描述：

  1-[(tetrahydropyran-2-yl)oxy]non-3-yne 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.58h， 生成 1-Bromo-3-(3-nonynyloxymethyl)benzene
  参考文献：
  名称：

  (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases

  摘要：

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.

  DOI：

  10.1021/jm9606047

文献信息

• Aryl aliphatic acids
  申请人：Board of Governors of Wayne State University

  公开号：US05238832A1

  公开（公告）日：1993-08-24

  Novel aryl aliphatic acids or derivatives thereof of the general formula R--(C.sub.x --C.sub.y)--(C.sub.m H.sub.2m)--G--C(R.sup.1).sub.2 --Ar--(C.sub.n H.sub.2n)--COOR.sup.2 are described which exhibit inhibiting activity against 12-lipoxygenase. The compounds are characterized by having a low level of toxicity. Also included are salts and esters of the aliphatic acids.

  题目描述了一种具有抑制12-脂氧合酶活性的新型芳基脂肪羧酸或其衍生物，具有低毒性，还包括这些脂肪酸的盐和酯。
• US5238832A
  申请人：——

  公开号：US5238832A

  公开（公告）日：1993-08-24
• [EN] ARYL ALIPHATIC ACIDS<br/>[FR] ACIDES ALIPHATIQUES D'ARYLE
  申请人：BOARD OF GOVERNORS OF WAYNE STATE UNIVERSITY

  公开号：WO1993025521A1

  公开（公告）日：1993-12-23

  (EN) Novel aryl aliphatic acids or derivatives thereof of the general formula: R-(Cx-Cy)-(CmH2m)-G-C(R1)2-Ar-(CnH2n)-COOR2 are described which exhibit inhibiting activity against 12-lipoxygenase. The compounds are characterized by having a low level of toxicity. Also included are salts and esters of the aliphatic acids.(FR) L'invention se rapporte à de nouveaux acides aliphatiques d'aryle, ou à des dérivés de ceux-ci, répondant à la formule générale: R-(Cx-Cy)-(CmH2m)-G-C(R1)2-Ar-(CnH2n)-COOR2 et agissant comme inhibiteurs de 12-lipoxygénase. Ces composés sont caractérisés par un faible niveau de toxicité. Des sels et esters de ces acides aliphatiques sont également décrits.