((2E,6E)-8-(benzyloxy)-2,6-dimethylocta-2,6-dienyl)(phenyl)sulfane | 141245-02-5

• 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: ((2E,6E)-8-(benzyloxy)-2,6-dimethylocta-2,6-dienyl)(phenyl)sulfane
• 英文别名: [(2E,6E)-2,6-dimethyl-8-phenylmethoxyocta-2,6-dienyl]sulfanylbenzene
• CAS: 141245-02-5
• 化学式: C₂₃H₂₈OS
• 分子量: 352.541
• InChiKey: ZZOYMVWQWSUJNG-BJKXBBROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((2E,6E)-8-(benzyloxy)-2,6-dimethylocta-2,6-dienyl)(phenyl)sulfane 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三丁基膦 、 三正丁基氢锡 、 lithium 、 乙胺 、 naphthalen-1-yl-lithium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 10.0h， 生成 ((2E)-5-(1,2,3,4,4a,5,8,8a-octahydro-1,1,4a,6-tetramethylnaphthalen-5-yl)-3-methylpent-2-enyl)(phenyl)sulfane
  参考文献：
  名称：

  Reinforcing effect of bi- and tri-cyclopolyprenols on ‘primitive’ membranes made of polyprenyl phosphates

  摘要：

  Cholesterol plays the role of membrane reinforcer in eukaryotes, whereas hopanoids play the same role in bacteria. Which components could have reinforced 'primitive' membranes? We describe here an efficient biomimetic synthesis of bi- and tri-cyclopolyprenols and demonstrate that these compounds reinforce the membranes of polyprenyl phosphate, which we speculated as 'primitive' membranes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.076
• 作为产物：
  描述：

  (E,E)-8-acetoxy-1-benzyloxy-3,7-dimethylocta-2,6-diene 、 二苯二硫醚 在 吡啶 、 三丁基膦 作用下， 以75%的产率得到((2E,6E)-8-(benzyloxy)-2,6-dimethylocta-2,6-dienyl)(phenyl)sulfane
  参考文献：
  名称：

  Reinforcing effect of bi- and tri-cyclopolyprenols on ‘primitive’ membranes made of polyprenyl phosphates

  摘要：

  Cholesterol plays the role of membrane reinforcer in eukaryotes, whereas hopanoids play the same role in bacteria. Which components could have reinforced 'primitive' membranes? We describe here an efficient biomimetic synthesis of bi- and tri-cyclopolyprenols and demonstrate that these compounds reinforce the membranes of polyprenyl phosphate, which we speculated as 'primitive' membranes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.076

文献信息

• Synthesis of (±)-Isopiperitenol by Fluoride Ion Mediated Cyclization of Allylsilane Moiety Incorporated in Terpene Aldehydes
  作者：Hideshi Nakamura、Toyohisa Oya、Akio Murai

  DOI：10.1246/bcsj.65.929

  日期：1992.3

  Fluoride ion mediated cyclization of aldehydes (1 and 2) having regioisomeric allylsilane functionalities give a mixture of cis- and trans-isopiperitenol (3). The aldehydes (1) reacted faster and showed better stereoselectivity than the regioisomeric aldehydes (2) regardless of geometry of the double bond at an unsaturated aldehyde.

  在氟离子介导下，具有烯丙基硅烷官能团异构体的醛（1 和 2）发生环化反应，生成顺式和反式异哌啶醇（3）的混合物。无论不饱和醛双键的几何形状如何，醛（1）的反应速度和立体选择性均优于醛（2）的 Regioisomeric。
• Synthesis of Allylsilanes by Reductive Lithiation of Thioethers
  作者：Stéphane Streiff、Nigel Ribeiro、Laurent Désaubry

  DOI：10.1021/jo049237u

  日期：2004.10.1

  Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.