(3S,5S)-hepta-1,6-diene-3,5-diol | 185549-47-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5S)-hepta-1,6-diene-3,5-diol
• CAS: 185549-47-7
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: PEPISENPCDEXJK-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (3S,5S)-hepta-1,6-diene-3,5-diol 在 三乙烯二胺 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 8.67h， 生成 (1S,6S,8S)-8-vinyl-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
  参考文献：
  名称：

  P -Stereogenic双环[4.3.1]亚磷酸硼烷：可调P -Tether系统的合成和对C 2-对称的1,3-抗-Diol的去对称化作用

  摘要：

  报道了用于C 2对称二烯二醇去对称化的P-立体异构双环[4.3.1]亚磷酸硼烷系链系统的开发。该报告重点介绍了初步研究，包括系链的安装和去除以及通过二酰亚胺还原或交叉复分解实现的环外烯烃的化学选择性官能化。最值得注意的是，发散的氧化策略允许将双环亚磷酸酯硼烷络合物转化为相应的磷酸盐或硫代磷酸盐系统，从而突出了该P-系链系统的电子衰减。

  DOI：

  10.1021/acs.orglett.7b00851
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 正丁基锂 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (3S,5S)-hepta-1,6-diene-3,5-diol
  参考文献：
  名称：

  Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

  摘要：

  Protected 4-hydroxycyclopentenones (4-HCPs) constitute an important class of intermediates in chemical synthesis. A route to this class of compound has been developed. Key steps include Noyori reduction (which establishes the stereochemistry of the product), ring-closing metathesis, and simple functional group conversions to provide a set of substituted 4-HCPs in either enantiomeric form.

  DOI：

  10.1021/jo402539p

文献信息

• Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries
  作者：Gurpreet Singh、Jeffrey Aubé

  DOI：10.1039/c6ob00598e

  日期：——

  A series of 1,3-diols has been synthesized and used to create a pilot library of spatially diverse compounds.

  一系列1,3-二醇已经合成并用于创建一个空间多样化化合物的试验库。
• Flexible molecules with defined shape. Part 3. Conformational analysis of bis(tetrahydropyran-2-yl)methanes
  作者：Reinhard W. Hoffmann、B. Colin Kahrs、Jan Schiffer、J�rg Fleischhauer

  DOI：10.1039/p29960002407

  日期：——

  (R,R)-Bis(tetrahydropyran-2-yl)methane 4 along with its racemate have been synthesized. MM3 calculations suggest that the conformer 4a should be populated to ca. 85% in the conformer equilibrium. Analysis of the 1H NMR coupling constants show that one conformer predominates by about 9 : 1. That this is the conformer 4a is shown by various NMR techniques, as well as by comparison of calculated with measured CD spectroscopic data. The study is extended to the methyl-substituted bis(tetrahydropyranyl)methanes 21 and 23 which show, as predicted from MM3 calculations, essentially mono-conformational behaviour.

  (R,R)-双(四氢吡喃-2-基)甲烷4及其外消旋体已经合成。 MM3 计算表明构象异构体 4a 应填充到大约。 85%处于构象异构体平衡。 1H NMR耦合常数的分析表明，一种构象异构体占主导地位，比例约为9:1。通过各种NMR技术以及通过计算的CD光谱数据与测量的CD光谱数据的比较，表明这是构象异构体4a。该研究扩展到甲基取代的双（四氢吡喃基）甲烷 21 和 23，正如 MM3 计算所预测的那样，它们基本上显示出单构象行为。
• 10.1021/0l1002913
  作者：Venukadasula, Phanindra K. M.、Chegondi, Rambabu、Maitra, Soma、Hanson, Paul R.

  DOI：10.1021/0l1002913

  日期：——
• Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach
  作者：Paul R. Hanson、Rambabu Chegondi、John Nguyen、Christopher D. Thomas、Joshua D. Waetzig、Alan Whitehead

  DOI：10.1021/jo2003506

  日期：2011.6.3

  The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.
• Multivalent Activation in Temporary Phosphate Tethers:  A New Tether for Small Molecule Synthesis
  作者：Alan Whitehead、Matthew D. McReynolds、Joel D. Moore、Paul R. Hanson

  DOI：10.1021/ol0512886

  日期：2005.7.1

  A new tether for small molecule synthesis is reported. This functionally active tether mediates the desymmetrization of a pseudo-C-2-symmetric tris-allylic phosphate triester to generate a P-chiral bicyclo[4.3.1]phosphate containing ample steric and stereoelectronic differentiation for investigating chemo-, regio-, and stereoselective transformations. Overall, the method reported herein demonstrates a fundamentally new role of phosphates in synthesis and provides differentiated polyol building blocks for use in natural product synthesis.