(S)-6-(tert-Butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)hex-1-ene | 334972-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-6-(tert-Butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)hex-1-ene
• 英文别名: (S)-tert-butyl((2-((4-methoxybenzyl)oxy)hex-5-en-1-yl)oxy)dimethylsilane；(S)-(2-(4-methoxybenzyloxy)hex-5-enyloxy)(tert-butyl)dimethylsilane；tert-butyl-[(2S)-2-[(4-methoxyphenyl)methoxy]hex-5-enoxy]-dimethylsilane
• CAS: 334972-54-2
• 化学式: C₂₀H₃₄O₃Si
• 分子量: 350.574
• InChiKey: JLLYPJXZMRQPJI-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-6-(tert-Butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)hex-1-ene 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 18-冠醚-6 、 potassium tert-butylate 、 sodium hexamethyldisilazane 、 二甲基氯化铝 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium bromide 、 叔丁醇 、 甲基磺酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 生成 (1S,1'S,2R,2'R,5R,5'R)-2,2'-{5,5'-[Butane-1,4-diylidene]bis[(2R,5Z)-tetrahydropyran-2-yl]}bis[1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane]
  参考文献：
  名称：

  Synthesis of (+)-testudinariol A, a triterpene metabolite of the marine mollusc Pleurobrancus testudinarius

  摘要：

  Testudinariol A (1) is an ichthyotoxic and structurally unusual triterpene alcohol isolated from the skin and the mucus of the marine mollusc Pleurobrancus testudinarius. A stereoselective synthesis of (+)-1 was achieved by starting from (R)-glycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02179-1
• 作为产物：
  描述：

  (S)-hex-5-ene-1,2-diol 在 4-二甲氨基吡啶 、 三氟甲磺酸 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-6-(tert-Butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)hex-1-ene
  参考文献：
  名称：

  三萜全合成。第6部分。海洋软体动物Pleurobrancus testudinarius的三萜代谢产物-睾丸甾醇A和B的合成

  摘要：

  Testudinariols A（1）和B（1'）具有鱼毒力，结构不寻常。三萜 酒类从海洋软体动物胸腔胸ran的皮肤和粘液中分离出来的。（+）- 1和（+）- 1'的第一个合成是通过从（R）-缩水甘油。

  DOI：

  10.1039/b100777g

文献信息

• Formal synthesis of pinolide via l-proline-catalyzed sequential α-aminooxylation, Horner–Wadsworth–Emmons olefination and Sharpless asymmetric dihydroxylation
  作者：Anil M. Shelke、Gurunath Suryavanshi

  DOI：10.1016/j.tetasy.2016.01.005

  日期：2016.2

  A convergent, formal enantioselective synthesis of pinolide, a new nonenolide, has been achieved with high enantiomeric purity (99% ee) starting from readily available raw materials. The main highlight of the synthetic strategy is the application of L-proline catalyzed sequential alpha-aminooxylation and Horner-Wadsworth-Emmons olefination of an aldehyde, Sharpless asymmetric dihydroxylation and Steglich esterification as the key steps for the construction of a key chiral intermediate of the target molecule. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation
  作者：Nicolaas A. Vermeulen、Jared H. Delcamp、M. Christina White

  DOI：10.1021/ja104826g

  日期：2010.8.18

  A highly general, predictably selective C H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (1 6 examples, EIZ L- 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C H oxidation vs C C bond-forming methods are evaluated and discussed in four "case studies".
• Triterpenoid total synthesis. Part 6. Synthesis of testudinariols A and B, triterpene metabolites of the marine mollusc Pleurobrancus testudinarius.
  作者：Masao Yoshida、Hirosato Takikawa、Kenji Mori

  DOI：10.1039/b100777g

  日期：——

  Testudinariols A (1) and B (1′) are ichthyotoxic and structurally unusual triterpene alcohols isolated from the skin and the mucus of the marine mollusc Pleurobrancus testudinarius. The first synthesis of (+)-1 and (+)-1′ was achieved by starting from (R)-glycidol.

  Testudinariols A（1）和B（1'）具有鱼毒力，结构不寻常。三萜 酒类从海洋软体动物胸腔胸ran的皮肤和粘液中分离出来的。（+）- 1和（+）- 1'的第一个合成是通过从（R）-缩水甘油。
• Synthesis of (+)-testudinariol A, a triterpene metabolite of the marine mollusc Pleurobrancus testudinarius
  作者：Hirosato Takikawa、Masao Yoshida、Kenji Mori

  DOI：10.1016/s0040-4039(00)02179-1

  日期：2001.2

  Testudinariol A (1) is an ichthyotoxic and structurally unusual triterpene alcohol isolated from the skin and the mucus of the marine mollusc Pleurobrancus testudinarius. A stereoselective synthesis of (+)-1 was achieved by starting from (R)-glycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.