(5S,6S)-5,6-dihydroxydeca-1,9-diene | 221467-95-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5S,6S)-5,6-dihydroxydeca-1,9-diene
• 英文别名: (5S,6S)-1,9-decadiene-5,6-diol；(5S,6S)-deca-1,9-diene-5,6-diol
• CAS: 221467-95-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: UCQXMRCBVKGCOE-UWVGGRQHSA-N

物化性质

• 沸点：
  279.7±40.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5,6-dihydroxydeca-1,9-diene 在 palladium on activated charcoal 、 Co(modp)2 叔丁基过氧化氢 、 草酰氯 、 copper(I) bromide dimethylsulfide complex 、 potassium tert-butylate 、 氢气 、 氧气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， -78.0~60.0 ℃ 、101.33 kPa 条件下， 反应 53.0h， 生成
  参考文献：
  名称：

  Bulladecin 型乙酰生成素的简便途径 - 阿西米洛宾的全合成及其四氢呋喃段的构型校正

  摘要：

  建立了合成反式/苏式/反式-双（四氢呋喃）（THF）环单元的最有效方法，然后分十二步和十四步完成了（-）-阿西米洛宾及其非对映体的首次全合成，分别从反式 1,5,9-癸三烯，通过收敛路线，以 Wittig 反应为关键步骤。凭借这些合成结果，天然存在的阿西洛宾中双 (THF) 单元的绝对构型应该得到纠正。

  DOI：

  10.1002/(sici)1099-0690(200001)2000:2<349::aid-ejoc349>3.0.co;2-j
• 作为产物：
  描述：

  1,5,9-decatriene 以57%的产率得到(5S,6S)-5,6-dihydroxydeca-1,9-diene
  参考文献：
  名称：

  立体选择性合成的顺式-2,5-二取代的THF：在产丙酮酸甘油酯的相邻双THF核中的应用

  摘要：

  在甲硅烷基烯醇醚的存在下，γ，δ-不饱和醇的碘环化通过甲硅烷氧基中间体在一个罐中产生了顺式-2,5-二取代的四氢呋喃。N-碘代琥珀酰亚胺（NIS）有效地用作底物和甲硅烷基烯醇醚中双键的活化剂。还描述了用于具有顺/苏/顺/顺相对立体化学的壬基产乙酸原的相邻双-四氢呋喃核的合成的应用。

  DOI：

  10.1021/ol203425p

文献信息

• Stereocontrolled construction of the trans-tetrahydrofuran units in Annonaceous acetogenins
  作者：Shi-Kai Tian、Zhi-Min Wang、Jian-Kang Jiang、Min Shi

  DOI：10.1016/s0957-4166(99)00259-1

  日期：1999.7

  the construction of trans-tetrahydrofuran (THF) unit from trans-1,5,9-decatriene was successfully developed by means of Sharpless AD reactions and oxidative cyclizations catalyzed by Co(modp)2 under an oxygen atmosphere. Based on this new synthetic strategy, the trans-mono-THF unit, trans-bis-THF unit and trans-tris-THF unit in Annonaceous acetogenins were smoothly obtained.

  借助Sharpless AD反应和氧气氛下Co（modp）2催化的氧化环化反应，成功开发了由反式-1,5,9-癸三烯构建反式四氢呋喃（THF）单元的有效合成方法。基于这种新的合成策略，顺利地获得了无水醋酸原素中的反式-单-THF单元，反式-双-THF单元和反式-tris-THF单元。
• Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines
  作者：Stefano Nicolai、Jérôme Waser

  DOI：10.1021/ol2029383

  日期：2011.12.2

  The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of acetylenes is further exploited to access key building blocks for the synthesis of bioactive natural products.
• A facile route to the total synthesis of gigantetrocin A
  作者：Zhi-Min Wang、Shi-Kai Tian、Min Shi

  DOI：10.1016/s0957-4166(99)00039-7

  日期：1999.2

  A highly efficient synthetic method of the trans-mono-tetrahydrofuran (THF) ring building block was established and the title compound synthesized in 19 steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.
• The synthesis of asimilobin and the correction of its tetrahydrofuran segment's configuration
  作者：Zhi-Min Wang、Shi-Kai Tian、Min Shi

  DOI：10.1016/s0040-4039(98)02577-5

  日期：1999.1

  A highly efficient synthetic method for the trans/threo/trans- bis-tetrahydrofuran (THF) ring building block was established. The title compound was synthesized in thirteen steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step. The absolute configuration of the THF segment of naturally occurring asimilobin should be corrected. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity
  作者：Subhash C. Sinha、Zhiyong Chen、Zheng-Zheng Huang、Eiko Nakamaru-Ogiso、Halina Pietraszkiewicz、Matthew Edelstein、Frederick Valeriote

  DOI：10.1021/jm801028c

  日期：2008.11.27

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.