(S)-1-(trimethylsilyl)pentadec-1-yn-3-ol | 619315-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(trimethylsilyl)pentadec-1-yn-3-ol
• 英文别名: (S)-1-trimethylsilyl-1-pentadecyn-3-ol；(3S)-1-trimethylsilylpentadec-1-yn-3-ol
• CAS: 619315-47-8
• 化学式: C₁₈H₃₆OSi
• 分子量: 296.569
• InChiKey: DBDWZPXZZYGCDK-SFHVURJKSA-N

物化性质

• 沸点：
  371.1±15.0 °C(Predicted)
• 密度：
  0.865±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-(trimethylsilyl)pentadec-1-yn-3-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 tert-Butyl-((S)-1-ethynyl-tridecyloxy)-diphenyl-silane
  参考文献：
  名称：

  Electrophilic selenocyclization in 2-ene-1,5-diol systems: unexpected oxetane vs. tetrahydrofuran formation

  摘要：

  Electrophile-induced cyclization of (E)- and (Z)-2-ene-1,5-diols to tetrahydrofurans and oxetanes is described. Significant differences between the present report and previous work have been noted. A tentative model is proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01134-7
• 作为产物：
  描述：

  十三酰氯 在 三氯化铝 、 (S)-alpine borane 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (S)-1-(trimethylsilyl)pentadec-1-yn-3-ol
  参考文献：
  名称：

  Electrophilic selenocyclization in 2-ene-1,5-diol systems: unexpected oxetane vs. tetrahydrofuran formation

  摘要：

  Electrophile-induced cyclization of (E)- and (Z)-2-ene-1,5-diols to tetrahydrofurans and oxetanes is described. Significant differences between the present report and previous work have been noted. A tentative model is proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01134-7

文献信息

• Synthesis and Absolute Configuration of 6-Hydroxylated New Ceramides in Human Skin, Ceramides B, 4, 7 and 8
  作者：Yui Masuda、Kenji Mori

  DOI：10.1002/ejoc.200500357

  日期：2005.11

  assigned to three new ceramides isolated from human skin such as ceramide B [1, (2S,3R,4E,6R)-6-hydroxy-N-(30′-hydroxytriacontanoyl)-4-sphingenine], ceramide 8 [2, (2S,3R,4E,6R)-6-hydroxy-N-(tetracosanoyl)-4-sphingenine] and ceramide 4 3, (2S,3R,4E,6R)-6-hydroxy-N-[(30′-linoleoyloxy)triacontanoyl]-4-sphingenine}. (6R,2′R)-Configuration was given to another ceramide in human skin, ceramide 7 [4, (2S,3R,4E

  6R-构型被分配给三种从人类皮肤中分离的新神经酰胺，如神经酰胺 B [1, (2S,3R,4E,6R)-6-羟基-N-(30'-羟基三十二酰基)-4-鞘氨醇]、神经酰胺 8 [2, (2S,3R,4E,6R)-6-羟基-N-(二十四烷酰基)-4-鞘氨醇]和神经酰胺43,(2S,3R,4E,6R)-6-羟基-N-[ (30'-亚油酰氧基)三十烷酰基]-4-鞘氨醇}。(6R,2'R)-构型赋予人类皮肤中的另一种神经酰胺，神经酰胺 7 [4, (2S,3R,4E,6R,2'R)-6-羟基-N-(2'-羟基二十烷酰基)- 4-鞘氨醇]。通过酶促制备 1-pentadecyn-3-ol 的对映异构体和 2-羟基二十二烷酸的对映异构体，使这些分配成为可能。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis and stereochemistry of ceramide B, (2S,3R,4E,6R)-N-(30-hydroxytriacontanoyl)-6-hydroxy-4-sphingenine, a new ceramide in human epidermis
  作者：Kenji Mori、Yui Masuda

  DOI：10.1016/j.tetlet.2003.10.025

  日期：2003.12

  pentadecan-15-olide, the enantiomers of 1-pentadecyn-3-ol, and (S)-Garner's aldehyde. Comparison of the 1H NMR spectra of the tetraacetyl derivatives of 1 and 1′ with that of ceramide B, a new protein-bound ceramide in human stratum corneum, revealed it to be (2S,3R,4E,6R)-1.

  以十五烷为原料合成（2 S，3 R，4 E，6 R）-N-（30-羟基三tri酰基）-6-羟基-4-鞘氨醇（1）及其（6 S）-异构体（1 '）。 -15-内酰胺，1-戊炔-3-醇的对映体和（S）-加纳醛。1和1 '的四乙酰基衍生物与人角质层中一种新的蛋白结合型神经酰胺神经酰胺B的1 H NMR光谱比较表明，其为（2 S，3 R，4 E，6 R） - 1。
• Synthesis of 6-hydroxyceramide using ruthenium-catalyzed hydrosilylation–protodesilylation. Unexpected formation of a long periodicity lamellar phase in skin lipid membranes
  作者：Andrej Kováčik、Lukáš Opálka、Michaela Šilarová、Jaroslav Roh、Kateřina Vávrová

  DOI：10.1039/c6ra16565f

  日期：——

  The synthesis of a ceramide with a 6-hydroxysphingosine base, a unique component of the human epidermal barrier, is reported. The key step involves a mild and selective trans-reduction of a triple bond using [Cp*Ru(CH3CN)3]PF6-catalyzed hydrosilylation followed by protodesilylation. The oxidation of sphingosine-based ceramide to 6-hydroxyceramide is also described. X-Ray powder diffraction on the model

  据报道，具有人皮肤表皮屏障的独特成分的6-羟基鞘氨醇碱的神经酰胺的合成。关键步骤涉及使用[Cp * Ru（CH 3 CN）3 ] PF 6催化的氢化硅烷化进行轻度和选择性的三键反式还原，然后进行原型去甲硅烷基化。还描述了基于鞘氨醇的神经酰胺氧化为6-羟基神经酰胺。在模型皮肤脂质膜上进行的X射线粉末衍射表明，6-羟基神经酰胺以10.6 nm的周期性促进层状相的形成，这也许可以解释为什么角质形成细胞在碳6处羟基化了一些神经酰胺。
• Electrophilic selenocyclization in 2-ene-1,5-diol systems: unexpected oxetane vs. tetrahydrofuran formation
  作者：Pierre Van de Weghe、Stéphane Bourg、Jacques Eustache

  DOI：10.1016/s0040-4020(03)01134-7

  日期：2003.9

  Electrophile-induced cyclization of (E)- and (Z)-2-ene-1,5-diols to tetrahydrofurans and oxetanes is described. Significant differences between the present report and previous work have been noted. A tentative model is proposed. (C) 2003 Elsevier Ltd. All rights reserved.