2-(2-bromoethyl)-2,5,7,8-tetramethylchroman-6-yl acetate | 130266-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(2-bromoethyl)-2,5,7,8-tetramethylchroman-6-yl acetate
• 英文别名: 3,4-Dihydro-2-(2-bromoethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-yl acetate；3,4-dihydro-2-(2-bromoethyl)-2,5,7,8-tetramethyl-2H-2-benzopyran-6-yl acetate；3,4-dihydro-2-(2-bromoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate；[2-(2-bromoethyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] acetate
• CAS: 130266-63-6
• 化学式: C₁₇H₂₃BrO₃
• 分子量: 355.272
• InChiKey: VXMLCAVRCWKVJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  424.2±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-bromoethyl)-2,5,7,8-tetramethylchroman-6-yl acetate 在 盐酸 、 basic resin AG-1-X₂ 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 3,4-dihydro-6-hydroxy-N,N,N,2,5,7,8-heptamethyl-2H-1-benzopyran-2-ethanaminium chloride
  参考文献：
  名称：

  A cardioselective, hydrophilic N,N,N-trimethylethanaminium .alpha.-tocopherol analog that reduces myocardial infarct size

  摘要：

  The alpha-tocopherol analogue 3,4-dihydro-6-hydroxy-N,N,N,2,5,7,8-heptamethyl-2H-1-benzopyran-2-ethanaminium 4-methylbenzenesulfonate (1a, MDL 73404) and its O-acetate 1b (MDL 74270) were synthesized. Compound 1a was found to be hydrophilic (log P = -0.60) and to prevent lipid autoxidation in rat brain homogenate with an IC50 of 1.7 +/- 0.9-mu-M. Tissue distribution studies with [C-14]-1b in rats (1 mg/kg iv) showed that radioactivity accumulates in the heart (ratio 20:1 vs blood after 1 h). Infusion of 1 mg/kg per h of 1b bromide reduced infarct size by 54% in rats subjected to coronary artery occlusion for 60 min followed by reperfusion for 30 min, compared to saline-infused controls. By comparison, the tertiary amine analogue 5 was found not to accumulate in heart tissue, to be an equally effective free-radical scavenger in vitro, but to require a higher dose to reduce infarct size in rats. This shows that the cardioselectivity of compound 1 contributes to its potency in salvaging myocardial tissue in rats after ischemia and reperfusion.

  DOI：

  10.1021/jm00105a040
• 作为产物：
  描述：

  2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol 在 乙酸酐 作用下， 以 2,3-二甲基吡啶 、 水 为溶剂， 生成 2-(2-bromoethyl)-2,5,7,8-tetramethylchroman-6-yl acetate
  参考文献：
  名称：

  Cardioprotective tocopherol analogs

  摘要：

  这项发明涉及某些2H-1-苯并吡喃的烷基化膦銨烯衍生物，以及用于它们的制备的中间体和过程，以及它们的自由基清除剂和心脏保护特性，以及它们作为治疗剂的最终应用。

  公开号：

  EP0535283A1

文献信息

• Defunctionalization of sp³ C–Heteroatom and sp³ C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts
  作者：Yiting Gu、Hongfei Yin、Matthew Wakeling、Juzeng An、Ruben Martin

  DOI：10.1021/acscatal.1c05329

  日期：2022.1.21

  defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence

  公开了一种使用三线态酮催化剂和联吡啶添加剂实现 sp 3 C-杂原子和 sp 3 C-C 键的光诱导去功能化的一般策略。该协议的特点是其范围广泛，无需使用过渡金属催化剂或化学计量外源还原剂，从而为激活 σ sp 3 C-C（杂原子）键提供了一种补充技术。初步机理研究表明，2,2'-联吡啶的存在提高了酮基自由基中间体的寿命。
• Cholesterol-lowering tocopherol analogs
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05135945A1

  公开（公告）日：1992-08-04

  This invention relates to alkylamino alkylene derivatives of certain 2H-1-benzopyrans useful as plasma cholesterol lowering agents and to their end-use application as therapeutic agents.

  这项发明涉及某些2H-1-苯并吡喁酮的烷基氨基烷基衍生物，可用作降低血浆胆固醇的药物，并涉及它们作为治疗剂的最终应用。
• Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO₂
  作者：Yu Liu、Josep Cornella、Ruben Martin

  DOI：10.1021/ja5064586

  日期：2014.8.13

  A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atmospheric pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids.
• GRISAR, J. MARTIN;PETTY, MARGARET A.;BOLKENIUS, FRANK N.;DOW, JAMES;WAGNE+, J. MED. CHEM., 34,(1991) N, C. 257-260
  作者：GRISAR, J. MARTIN、PETTY, MARGARET A.、BOLKENIUS, FRANK N.、DOW, JAMES、WAGNE+

  DOI：——

  日期：——
• GRISAR, J. MARTIN;PETTY, MARGARET;BOLKENIUS, FRANK
  作者：GRISAR, J. MARTIN、PETTY, MARGARET、BOLKENIUS, FRANK

  DOI：——

  日期：——