1-(4-bromobenzyl)-4-methyl-2,6,7-trioxabiyclo[2.2.2]octane | 251359-05-4

• 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-(4-bromobenzyl)-4-methyl-2,6,7-trioxabiyclo[2.2.2]octane
• 英文别名: 1-(4-Bromobenzyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane；1-[(4-bromophenyl)methyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 251359-05-4
• 化学式: C₁₃H₁₅BrO₃
• 分子量: 299.164
• InChiKey: BEGAZMIAWNNVNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-4-methyl-2,6,7-trioxabiyclo[2.2.2]octane 在 吡啶 、 盐酸 、 六甲基磷酰三胺 、 lithium hydroxide 、 正丁基锂 、 氯化亚砜 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 {4-[1-(3,4-Bis-difluoromethoxy-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-acetic acid 3-hydroxy-2-hydroxymethyl-2-methyl-propyl ester
  参考文献：
  名称：

  Discovery of L-791,943: A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor

  摘要：

  Structure-activity relationship studies directed toward improving the potency and metabolic stability of CDP-840 (3) resulted in the discovery of L-791,943 (1 In) as a potent (HWB TNF-alpha = 0.67 muM) and orally active phosphodiesterase type 4 (PDE4) inhibitor. This compound, which bears a stable bis-difluoromethoxy catechol and a pendant hexafluorocarbinol, exhibited a long half-life in rat and in squirrel monkey. It is well tolerated in ferret with an emetic threshold greater than 30 mg/kg (po) and was found to be active in the ovalbumin-induced bronchoconstriction model in guinea pig and in the ascaris-induced bronchoconstriction models in sheep and squirrel monkey. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00190-7
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(4-bromobenzyl)-4-methyl-2,6,7-trioxabiyclo[2.2.2]octane
  参考文献：
  名称：

  1-(4-溴苄基)-4-甲基-2,6,7-三氧杂双环[2.2.2]辛烷的合成及晶体结构

  摘要：

  摘要 1-(4-Bromobenzyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane, C13H15BrO3, 已由 4-溴苯乙酸氯通过氧杂环丁烷酯 (3-methyl-3-oxetanyl) 合成2-(4-溴苯基)乙酸甲酯。标题化合物的晶体结构已在低温 (120 K) 下通过 X 射线衍射法测定。该化合物在单斜空间群 P21/n (No. 14) 中结晶，Z = 4，晶格参数 a = 6.019(5), b = 20.990(5), c = 9.915(2) Å, β = 101.29( 1)°。

  DOI：

  10.1023/a:1009531514664

文献信息

• Discovery of L-791,943: A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor
  作者：Daniel Guay、Pierre Hamel、Marc Blouin、Christine Brideau、Chi Chung Chan、Nathalie Chauret、Yves Ducharme、Zheng Huang、Mario Girard、Tom R. Jones、France Laliberté、Paul Masson、Malia McAuliffe、Hanna Piechuta、José Silva、Robert N. Young、Yves Girard

  DOI：10.1016/s0960-894x(02)00190-7

  日期：2002.6

  Structure-activity relationship studies directed toward improving the potency and metabolic stability of CDP-840 (3) resulted in the discovery of L-791,943 (1 In) as a potent (HWB TNF-alpha = 0.67 muM) and orally active phosphodiesterase type 4 (PDE4) inhibitor. This compound, which bears a stable bis-difluoromethoxy catechol and a pendant hexafluorocarbinol, exhibited a long half-life in rat and in squirrel monkey. It is well tolerated in ferret with an emetic threshold greater than 30 mg/kg (po) and was found to be active in the ovalbumin-induced bronchoconstriction model in guinea pig and in the ascaris-induced bronchoconstriction models in sheep and squirrel monkey. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and crystal structure of 1-(4-bromobenzyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
  作者：Marianne Sveaas Løiten、Christian Gløgård、Jo Klaveness、Berit Fj\\sgmaelig;rtoft

  DOI：10.1023/a:1009531514664

  日期：1999.4

  Abstract1-(4-Bromobenzyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane, C13H15BrO3, has been synthesized from 4-bromophenylacetic acid chloride via the oxetan ester (3-methyl-3-oxetanyl)methyl-2-(4-bromophenyl)acetate. The crystal structure of the title compound has been determined at low temperature (120 K), by X-ray diffraction methods. This compound crystallizes in the monoclinic space group P21/n

  摘要 1-(4-Bromobenzyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane, C13H15BrO3, 已由 4-溴苯乙酸氯通过氧杂环丁烷酯 (3-methyl-3-oxetanyl) 合成2-(4-溴苯基)乙酸甲酯。标题化合物的晶体结构已在低温 (120 K) 下通过 X 射线衍射法测定。该化合物在单斜空间群 P21/n (No. 14) 中结晶，Z = 4，晶格参数 a = 6.019(5), b = 20.990(5), c = 9.915(2) Å, β = 101.29( 1)°。