all-trans-2,4,6,8-decatetraene | 64550-72-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: all-trans-2,4,6,8-decatetraene
• 英文别名: 2,4,6,8-Decatetraene；decatetraene；deca-2t,4t,6t,8t-tetraene；Deca-2t,4t,6t,8t-tetraen；(2E,4E,6E,8E)-2,4,6,8-decatetraene；(2E,4E,6E,8E)-deca-2,4,6,8-tetraene
• CAS: 64550-72-7
• 化学式: C₁₀H₁₄
• 分子量: 134.221
• InChiKey: ASZYCCVVQCKBIH-MIIZMDLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  反-2-丁烯 、 all-trans-2,4,6,8-decatetraene 生成 2,4-已二烯
  参考文献：
  名称：

  WOERLEE, E. F. G.;BOSMA, R. H. A.;EIJL, J. M. M. VAN;MOL, J. C., APPL. CATAL., 1984, 10, N 2, 219-229

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E,8E)-Deca-2,8-dien-5-yne-4,7-diol 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 all-trans-2,4,6,8-decatetraene
  参考文献：
  名称：

  Investigation of a Mechanism for Accelerated Breakdown of Immune Tolerance to the Primary Biliary Cirrhosis–Associated Autoantigen, Pyruvate Dehydrogenase Complex

  摘要：

  Primary biliary cirrhosis (PBC) is an autoimmune liver disease characterized by autoreactive T- and B-cell responses to the highly conserved enzyme pyruvate dehydrogenase complex (PDC). In this study we have examined the breakdown of T-cell tolerance to self-PDC using a mouse model. Female SJL/J mice were sensitized intraperitoneally with foreign-PDC (bovine) and/or self-PDC (murine) in complete Freund's adjuvant, and serum, spleen, and liver tissue was taken 8 weeks later. Animals sensitized with foreign-PDC produced IgG antibodies that were reactive with both foreign and self-PDC, but splenic T cells from these animals only responded to stimulation with foreign PDC. Sensitization with self-PDC elicited neither antibodies nor reactive T cells. Significantly, cosensitization with mixed self-PDC and foreign-PDC resulted in a full breakdown of self-tolerance, with generation of both antibody and T-cell responses to self-PDC of the type seen exclusively in human PBC patients. Mild bile duct lesions deficient in CD8(+) T cells were seen 8 weeks after sensitization with either foreign or self-PDC. However, after sensitization with mixed self-PDC and foreign-PDC, these lesions were significantly larger and heavily infiltrated by CD8(+) T cells. Liver-infiltrating T cells derived from the self-PDC and foreign-PDC cosensitized but not from control animals showed reactivity with self-PDC, suggesting a possible role for autoreactive PDC-specific T-cell responses in the pathogenesis of the observed histologic changes. It is likely that B-cell cross-reactivity between foreign and self-PDC enhances the potential for breakdown of T-cell self-tolerance by allowing efficient presentation of self-antigens in the inoculum. This model may provide a useful system for investigating the etiology and treatment of PBC.

  DOI：

  10.1038/labinvest.3780413

文献信息

• Pentadienyl dithiocarbamate as a 1,5-dianion equivalent. Versatile reagent for polyene synthesis
  作者：Toshio Hayashi、Isaburo Hori、Takeshi Oishi

  DOI：10.1021/ja00347a072

  日期：1983.5
• Domino pericyclic reactions of acyclic conjugated (E,Z,E,E)-tetraenes
  作者：Danielle Skropeta、Rodney W. Rickards

  DOI：10.1016/j.tetlet.2007.03.011

  日期：2007.4

  Acyclic conjugated (E,Z,E,E)-tetraenes, upon thermolysis, undergo a domino pericyclic process involving 6 pi electrocyclisation of the (E,Z,E)-triene moiety to give the corresponding cis-disubstituted 5-vinyl-1,3-cyclohexadienes, followed by an intramolecular Diels-Alder reaction with the vinyl side chain to give tricyclo[3.2.1.0(2,7)]oct-3-enes. (c) 2007 Elsevier Ltd. All rights reserved.
• Spectroscopic and dynamical studies of the <i>S</i>₁ and <i>S</i>₂ states of decatetraene in supersonic molecular beams
  作者：Hrvoje Petek、Andrew J. Bell、Keitaro Yoshihara、Ronald L. Christensen

  DOI：10.1063/1.461749

  日期：1991.10

  Fluorescence and fluorescence excitation spectra of all-trans-2,4,6,8-decatetraene have been obtained in free jets and in inert-gas clusters. In isolated decatetraene, excitation into 1 1Bu (S2) results in emission from both S2 (1 1Bu→1 1Ag) and S1 (2 1Ag→1 1Ag) on time scales that are faster than the 10 ns experimental resolution. In clusters, rapid electronic and vibrational relaxation leads to long-lived (360 ns) emission from thermally relaxed levels of S1. Direct excitation of low-lying, S1 vibronic levels in cold, isolated molecules also results in long-lived S1→S0 fluorescence, as expected for this symmetry-forbidden transition. The detection of S1 emission in free decatetraene has permitted the first detailed study of the vibronic structure and kinetics of the 2 1Ag state of an isolated, all-trans linear polyene. The S1←S0 fluorescence excitation spectrum is rich in low-frequency vibronic progressions. Analysis of this spectrum suggests that the transition not only is made allowed by vibronic coupling involving low-frequency bu skeletal modes (Herzberg–Teller coupling), as for polyenes in condensed phases, but also gains intensity from interactions between the electronic motion and the hindered rotations (torsions) of the terminal methyl groups. Preliminary analysis suggests that the barriers to internal rotation of the methyl groups must be substantially reduced in the 2 1Ag (S1) state. For isolated decatetraene, the 2 1Ag fluorescence lifetimes show a monotonic decrease with increasing vibrational energy, presumably due to increased mixing with the 1 1Bu state.
• HAYASHI, TOSHIO;HORI, ISABURO;OISHI, TAKESHI, J. AMER. CHEM. SOC., 1983, 105, N 9, 2909-2911
  作者：HAYASHI, TOSHIO、HORI, ISABURO、OISHI, TAKESHI

  DOI：——

  日期：——
• Investigation of a Mechanism for Accelerated Breakdown of Immune Tolerance to the Primary Biliary Cirrhosis–Associated Autoantigen, Pyruvate Dehydrogenase Complex
  作者：David E J Jones、Jeremy M Palmer、Kate Bennett、Amanda J Robe、Stephen J Yeaman、Helen Robertson、Margaret F Bassendine、Alastair D Burt、John A Kirby

  DOI：10.1038/labinvest.3780413

  日期：2002.2

  Primary biliary cirrhosis (PBC) is an autoimmune liver disease characterized by autoreactive T- and B-cell responses to the highly conserved enzyme pyruvate dehydrogenase complex (PDC). In this study we have examined the breakdown of T-cell tolerance to self-PDC using a mouse model. Female SJL/J mice were sensitized intraperitoneally with foreign-PDC (bovine) and/or self-PDC (murine) in complete Freund's adjuvant, and serum, spleen, and liver tissue was taken 8 weeks later. Animals sensitized with foreign-PDC produced IgG antibodies that were reactive with both foreign and self-PDC, but splenic T cells from these animals only responded to stimulation with foreign PDC. Sensitization with self-PDC elicited neither antibodies nor reactive T cells. Significantly, cosensitization with mixed self-PDC and foreign-PDC resulted in a full breakdown of self-tolerance, with generation of both antibody and T-cell responses to self-PDC of the type seen exclusively in human PBC patients. Mild bile duct lesions deficient in CD8(+) T cells were seen 8 weeks after sensitization with either foreign or self-PDC. However, after sensitization with mixed self-PDC and foreign-PDC, these lesions were significantly larger and heavily infiltrated by CD8(+) T cells. Liver-infiltrating T cells derived from the self-PDC and foreign-PDC cosensitized but not from control animals showed reactivity with self-PDC, suggesting a possible role for autoreactive PDC-specific T-cell responses in the pathogenesis of the observed histologic changes. It is likely that B-cell cross-reactivity between foreign and self-PDC enhances the potential for breakdown of T-cell self-tolerance by allowing efficient presentation of self-antigens in the inoculum. This model may provide a useful system for investigating the etiology and treatment of PBC.