(6E)-8-methylenetridec-6-ene | 1044536-19-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (6E)-8-methylenetridec-6-ene
• 英文别名: (E)-8-methylidenetridec-6-ene
• CAS: 1044536-19-7
• 化学式: C₁₄H₂₆
• 分子量: 194.36
• InChiKey: HCMDLAUIZBRXNY-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (6E)-8-methylenetridec-6-ene 、 N-(2,6-diisopropylphenyl)-2-phenacylthioacetamide 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 7.0h， 以64%的产率得到
  参考文献：
  名称：

  ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes

  摘要：

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.

  DOI：

  10.1016/0968-0896(96)00143-5
• 作为产物：
  描述：

  1-庚炔 在 mercury(II) diacetate 、 三乙胺 、 copper dichloride 、 palladium dichloride 、 儿萘酚硼烷 作用下， 生成 (6E)-8-methylenetridec-6-ene
  参考文献：
  名称：

  ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes

  摘要：

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.

  DOI：

  10.1016/0968-0896(96)00143-5

文献信息

• Ti(OiPr)4/nBuLi: an attractive reagent system for [2+2+2] cyclotrimerisation reactions
  作者：V. A. Rassadin、E. Nicolas、Y. Six

  DOI：10.1039/c4cc02698e

  日期：——

  A convenient method for the [2+2+2] cyclotrimerisation of alkynes using Ti(OiPr)4/nBuLi is presented. Homotrimerisation of arylacetylenes proceeds within minutes with excellent regioselectivity. Moreover, the intermolecular construction of ABB heterotrimers can be achieved selectively from two different alkynes with similar electronic properties. The method is also suitable for the synthesis of pyridines.

  本文介绍了一种使用Ti(OiPr)4/nBuLi进行[2+2+2]环三聚化的便捷方法。芳基炔烃的同聚三聚在几分钟内进行，并且具有优异的区域选择性。此外，可以选择性地从两种具有相似电子特性的不同炔烃中合成ABB异聚三聚物。该方法也适用于吡啶的合成。
• Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions
  作者：Scott E. Denmark、Zhigang Wang

  DOI：10.1021/ol0156751

  日期：2001.4.1

  [GRAPHICS]The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.
• Reduction of Cp₂ZrCl₂ with Mischmetall:  A New Method for Generating an Efficient “Cp₂Zr” Equivalent
  作者：Clément Denhez、Sédami Médégan、Florence Hélion、Jean-Louis Namy、Jean-Luc Vasse、Jan Szymoniak

  DOI：10.1021/ol060712f

  日期：2006.7.1

  A "Cp2Zr" equivalent is generated under mild conditions (THF, room temperature) by reducing Cp2ZrCl2 with cheap and readily available mischmetall (an alloy of Ce, La, Nd, and Pr). Coupling reactions, including those of terminal alkynes, can efficiently be achieved by using this reagent.
• ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes
  作者：Richard G. Wilde、Jeffrey T. Billheimer、Sandie J. Germain、Elizabeth A. Hausner、Paul C. Meunier、Deborah A. Munzer、Janet K. Stoltenborg、Peter J. Gillies、Deborah L. Burcham、Shiew-Mai Huang、John D. Klaczkiewicz、Soo S. Ko、Ruth R. Wexler

  DOI：10.1016/0968-0896(96)00143-5

  日期：1996.9

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.