1-(4-O-tert-butyldiphenylsilyl-1-butynyl)-(1R)-2-octynyl alcohol | 342902-95-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(4-O-tert-butyldiphenylsilyl-1-butynyl)-(1R)-2-octynyl alcohol
• 英文别名: (5R)-1-{[tert-Butyl(diphenyl)silyl]oxy}dodeca-3,6-diyn-5-ol；(5R)-1-[tert-butyl(diphenyl)silyl]oxydodeca-3,6-diyn-5-ol
• CAS: 342902-95-8
• 化学式: C₂₈H₃₆O₂Si
• 分子量: 432.678
• InChiKey: FIUCLEGIMKGGSW-RUZDIDTESA-N

物化性质

• 沸点：
  526.2±50.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 、 1-(4-O-tert-butyldiphenylsilyl-1-butynyl)-(1R)-2-octynyl alcohol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 以86%的产率得到tert-Butyl-[(R)-5-(4-methoxy-benzyloxy)-dodeca-3,6-diynyloxy]-diphenyl-silane
  参考文献：
  名称：

  Novel chiral lipoxygenase substrates: design and synthesis. Part 2

  摘要：

  A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl, aryl and hydroxyl groups. The key steps in the synthesis involved enzymatic transesterification of 1,3-propanediol derivatives and two consecutive cis-selective Wittig olefinations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00009-5
• 作为产物：
  描述：

  2-辛炔-1-醇 在 咪唑 、 正丁基锂 、 草酰氯 、 lipase from Candida rugosa 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 34.33h， 生成 1-(4-O-tert-butyldiphenylsilyl-1-butynyl)-(1R)-2-octynyl alcohol
  参考文献：
  名称：

  Design and synthesis of useful intermediates for novel lipoxygenase substrates through enzymatic resolution

  摘要：

  Unnatural lipoxygenase substrates carrying spacing modifiers with a non-ionic hydroxy terminus and with methylene (flanked by the cis,cis diene moiety) pro-(S)-hydrogen can be synthesized from the intermediates la-lc. These intermediates are conveniently synthesized via enzymatic resolution with lipase in organic solvents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00495-x

文献信息

• Novel chiral lipoxygenase substrates: design and synthesis. Part 2
  作者：J.S. Yadav、S. Nanda

  DOI：10.1016/s0957-4166(02)00009-5

  日期：2001.12

  A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl, aryl and hydroxyl groups. The key steps in the synthesis involved enzymatic transesterification of 1,3-propanediol derivatives and two consecutive cis-selective Wittig olefinations. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of useful intermediates for novel lipoxygenase substrates through enzymatic resolution
  作者：J.S. Yadav、S. Nanda、A.Bhaskar Rao

  DOI：10.1016/s0957-4166(00)00495-x

  日期：2001.2

  Unnatural lipoxygenase substrates carrying spacing modifiers with a non-ionic hydroxy terminus and with methylene (flanked by the cis,cis diene moiety) pro-(S)-hydrogen can be synthesized from the intermediates la-lc. These intermediates are conveniently synthesized via enzymatic resolution with lipase in organic solvents. (C) 2001 Elsevier Science Ltd. All rights reserved.