1-Brom-4,8,12-trimethyl-tridecan | 88591-64-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-Brom-4,8,12-trimethyl-tridecan
• 英文别名: 1-Bromo-4,8,12-trimethyltridecane
• CAS: 88591-64-4
• 化学式: C₁₆H₃₃Br
• 分子量: 305.342
• InChiKey: YHEWNVRAEHESEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(2-benzylselenenyl-5-methoxy-3,4,6-trimethylphenyl)ethyl methyl ketone 、 1-Brom-4,8,12-trimethyl-tridecan 在 magnesium 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以48%的产率得到1-(2-benzylselenenyl-5-methoxy-3,4,6-trimethylphenyl)-3,7,11,15-tetramethyl-3-hexadecanol
  参考文献：
  名称：

  Synthesis and Antioxidant Profile of all-rac-α-Selenotocopherol

  摘要：

  all-rac-alpha-Selenotocopherol (6c) has been synthesized in 11 steps in 6.6% total yield. Key steps include chloromethylation to approach the persubstituted aromatic 9b and cyclization of alcohol precursor 10 by radical homolytic substitution at selenium to form the selenotocopherol heterocycle. Determination of the OH bond dissociation enthalpy (BDE) of 6c by electron paramagnetic resonance (EPR) equilibration techniques gave a value of 78.1 +/- 0.3 kcal mol(-1), approximately I kcal mol(-1) higher than that of a-tocopherol. Kinetic studies performed by measuring oxygen uptake of the induced oxidation of styrene in the presence of an antioxidant showed that selenotocopherol (6c) was a slightly poorer inhibitor than (x-tocopherol, in agreement with the BDE values. In contrast to simpler setenotocopherol analogues, 6c was not regenerable in the presence of a stoichiometric coreductant in a two-phase lipid peroxidation model.

  DOI：

  10.1021/jo052133e
• 作为产物：
  描述：

  假紫罗兰酮 在 乙醚 、 氢溴酸 、 镍 、 magnesium 作用下， 50.0~180.0 ℃ 、13.73 MPa 条件下， 生成 1-Brom-4,8,12-trimethyl-tridecan
  参考文献：
  名称：

  Smith; Sprung, Journal of the American Chemical Society, 1943, vol. 65, p. 1280

  摘要：

  DOI：

文献信息

• Intermediate phenolic compounds for the catalytic synthesis of chromans
  申请人：Hoffmann-La Roche Inc.

  公开号：US04598160A1

  公开（公告）日：1986-07-01

  A catalytic synthesis of chromans in racemic or optically active forms, including intermediates thereto; the synthesis employs an asymmetric palladium (II) catalyzed oxidative cyclization of a 2-homoallylphenol and provides intermediates useful in making chromans, especially vitamin E in racemic or optically active forms.

  一种催化合成光学活性或外消旋的香豆素，包括其中间体；该合成采用不对称钯（II）催化的氧化环化反应，反应物为2-同烯基苯酚，提供了制备香豆素的有用中间体，特别是制备光学活性或外消旋的维生素E。
• Long chain aliphatic halides and method of preparing same
  申请人：UNIV MINNESOTA

  公开号：US02421090A1

  公开（公告）日：1947-05-27
• Karrer et al., Helvetica Chimica Acta, 1948, vol. 31, p. 1510
  作者：Karrer et al.

  DOI：——

  日期：——
• Intramolecular Homolytic Substitution at Selenium:  Synthesis of Novel Selenium-Containing Vitamin E Analogues
  作者：Nawaf Al-Maharik、Lars Engman、Jonas Malmström、Carl H. Schiesser

  DOI：10.1021/jo010274k

  日期：2001.9.1

  Treatment of 1-(benzylselenenyl)-5-butyl-5-nonanoI (10) with oxalyl chloride followed by the sodium salt of N-hydroxypyridine-2-thione afforded the corresponding pyridine-2-thione-N-oxycarbonyI (PTOC) oxalate ester which was not isolated but immediately heated to provide 2,2-dibutylselenane (7). This transformation presumably involves a tertiary alkyl radical that undergoes intramolecular homolytic substitution at selenium with loss of the benzyl radical to provide the selenium-containing ring system (7). A similar protocol, when applied to 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl3-heptanol (18) and 1-(2-benzylselenenyl-5-methoxyphenyl)-3,7,11,15-tetramethyl-3-hexadecanoI (19), followed by deprotection, afforded the selenium-containing alpha -tocopherol analogues 4 and 1f, respectively, in moderate yields. To the best of our knowledge, these transformations represent the first examples of tertiary radicals involved in homolytic substitution chemistry at selenium.td2
• Smith; Rouault, Journal of the American Chemical Society, 1943, vol. 65, p. 748
  作者：Smith、Rouault

  DOI：——

  日期：——