6-(trimethylsilyl)-5-hexynyl methanesulfonate | 131353-19-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6-(trimethylsilyl)-5-hexynyl methanesulfonate
• 英文别名: 6-(trimethylsilyl)hex-5-ynyl methanesulfonate；6-Trimethylsilylhex-5-ynyl methanesulfonate
• CAS: 131353-19-0
• 化学式: C₁₀H₂₀O₃SSi
• 分子量: 248.418
• InChiKey: USUDCUJMMXDMBN-UHFFFAOYSA-N

物化性质

• 沸点：
  116-117 °C(Press: 0.4 Torr)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(trimethylsilyl)-5-hexynyl methanesulfonate 在 zinc(II) chloride 四丁基氟化铵 、 碘 、 magnesium 、 1,2-二溴乙烷 、 lithium bromide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 102.0h， 生成 (E)-4-methylundec-4-en-10-yn-1-ol
  参考文献：
  名称：

  [2+2+2]-4-羟基取代的烯二炔环加成成2-羟基取代的十氢菲

  摘要：

  从 4-戊炔-1-醇 (5) 开始，分七步制备烯二炔 rac-4，总产率为 31%。钴介导的这些烯二炔的 [2+2+2]-环加成和随后去除金属碎片以 37-56% 的产率提供了十氢菲 rac-3/13。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300432
• 作为产物：
  描述：

  6-<(trimethylsilyl)oxy>-1-(trimethylsilyl)-1-hexyne 在 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 2.0h， 生成 6-(trimethylsilyl)-5-hexynyl methanesulfonate
  参考文献：
  名称：

  Strong base-induced intramolecular cycloaddition of homophthalic anhydrides: an efficient synthesis of polycyclic peri-hydroxy aromatic compounds

  摘要：

  A strong-base-induced intramolecular cycloaddition reaction of homophthalic anhydrides has been examined as a method for preparing nonlinear polycyclic peri-hydroxy aromatic compounds.

  DOI：

  10.1021/jo00001a024

文献信息

• [EN] E-SELECTIN ANTAGONISTS<br/>[FR] ANTAGONISTES DE L'E-SÉLECTINE
  申请人：GLYCOMIMETICS INC

  公开号：WO2012037034A1

  公开（公告）日：2012-03-22

  Compounds, compositions and methods are provided for inhibiting in vitro and in vivo processes mediated by E-selectin binding. More specifically, particular glycomimetic compounds are described, wherein the compounds are E- selectin antagonists.

  提供了抑制E-选择素结合介导的体内外过程的化合物、组合物和方法。更具体地，描述了特定的糖类拟态化合物，其中这些化合物是E-选择素拮抗剂。
• The Scope of Catalytic Enantioselective Tandem Carbonyl Ylide Formation−Intramolecular [3 + 2] Cycloadditions
  作者：David M. Hodgson、Agnès H. Labande、Françoise Y. T. M. Pierard、María Á. Expósito Castro

  DOI：10.1021/jo0343735

  日期：2003.8.1

  Catalytic enantioselective tandem carbonyl ylide formation-intramolecular 1,3-dipolar cycloaddition reactions of 2-diazo-3,6-diketoesters show promising scope in terms of asymmetric induction as the tethered alkene/alkyne dipolarophile component is varied. Cycloadditions were found to occur in moderate to very good yields, with a difference in ee exhibited by the electronically different 2-diazo-3,6-diketoesters 1, 25 and 33, 34. Values for ee of up to 90% for alkene dipolarophiles and up to 86% for alkyne dipolarophiles were obtained.
• Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach
  作者：Jonas Egger、Céline Weckerle、Brian Cutting、Oliver Schwardt、Said Rabbani、Katrin Lemme、Beat Ernst

  DOI：10.1021/ja4029582

  日期：2013.7.3

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.
• KITA, YASUYUKI;OKUNAKA, RYUICHI;HONDA, TAKAO;SHINDO, MIKI;TANIGUCHI, MIYA+, J. ORG. CHEM., 56,(1991) N, C. 119-125
  作者：KITA, YASUYUKI、OKUNAKA, RYUICHI、HONDA, TAKAO、SHINDO, MIKI、TANIGUCHI, MIYA+

  DOI：——

  日期：——
• [2+2+2]-Cycloaddition of 4-Hydroxy-Substituted Enediynes to 2-Hydroxy-Substituted Decahydrophenanthrenes
  作者：Ulrich Groth、Norbert Richter、Aris Kalogerakis

  DOI：10.1002/ejoc.200300432

  日期：2003.12

  Enediynes rac-4 were prepared in seven steps with an overall yield of 31% starting from 4-pentyn-1-ol (5). A cobalt mediated [2+2+2]-cycloaddition of these enediynes and subsequent removal of the metal fragment afforded the decahydrophenanthrenes rac-3/13 in 37−56% yield. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  从 4-戊炔-1-醇 (5) 开始，分七步制备烯二炔 rac-4，总产率为 31%。钴介导的这些烯二炔的 [2+2+2]-环加成和随后去除金属碎片以 37-56% 的产率提供了十氢菲 rac-3/13。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)