(S,S)-4,5-dihydroxy-1,7-octadiyne | 171866-06-1

• 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: (S,S)-4,5-dihydroxy-1,7-octadiyne
• 英文别名: (4S,5S)-octa-1,7-diyne-4,5-diol
• CAS: 171866-06-1
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: OEMJPZULRMXSNJ-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S,S)-4,5-dihydroxy-1,7-octadiyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二氯二茂锆 sodium hydroxide 、 正丁基锂 、 十六烷基三甲基溴化铵 作用下， 以 四氢呋喃 、 二乙胺 为溶剂， 生成 (5S,6S)-1,3-Bis-(4-bromo-phenyl)-5,6-bis-octyloxy-4,5,6,7-tetrahydro-benzo[c]thiophene
  参考文献：
  名称：

  Zr-promoted cyclization of diynes bearing C2-chirality: synthesis and properties of new chiral conjugated molecules

  摘要：

  Conjugated oligomers bearing 4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene as a central linkage were synthesized by Negishi's reagent (n-Bu2ZrCp2) promoted intramolecular cyclization of a diyne and subsequent Suzuki coupling reactions. The chirality in the central linkage originated from tartaric acid, which induced the conjugated backbone of oligomers to exhibit interesting optical activity. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00520-8
• 作为产物：
  描述：

  (2S)-2-[(2S)-环氧乙烷-2-基]环氧乙烷 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以57%的产率得到(S,S)-4,5-dihydroxy-1,7-octadiyne
  参考文献：
  名称：

  过渡金属在有机合成中促进的乙炔异构化反应：（+）-（4S，5S）-多卡他霉素的合成

  摘要：

  乙炔-亚乙烯基重排已被用作（+）-（4S，5S）-多卡他霉素的对映体特异性合成中的关键步骤。

  DOI：

  10.1016/0040-4039(95)01681-7

文献信息

• Regioselective Cyclopolymerization of 1,7-Octadiynes
  作者：Stefan Naumann、Jörg Unold、Wolfgang Frey、Michael R. Buchmeiser

  DOI：10.1021/ma201749n

  日期：2011.11.8

  The regioselective cyclopolymerization of two structurally different 1,7-octadiynes, i.e. of 1,4-dihexyloxy-2,3-dipropargylbenzene (M1) and (R,R)/(S,S)-4,5-bis(trimethylsilyloxy)-1,7-octadiyne (M2) has been achieved with the modified Grubbs-Hoveyda-type metathesis initiator Ru(NCO)(2) (IMesH(2))(=CH-(2-(2-PrO)C6H4)) (I1, IMesH(2) = 1,3-dimesitylimidazolidin-2-ylidene) and with a series of Schrock initiators in the presence of quinuclidine, yielding conjugated polymers consisting virtually exclusively of 1,2-cyclohex-1-enylenvinylene units. In contrast to I1, Mo(N-2,6-(2-Pr)(2)C6H3) (CHCMe2Ph)(OCHMe2)(2) (I3) allows for establishing a living polymerization with M2 in the presence of quinuclidine. The structure of the polymers, which represent highly soluble and stable poly(acetylene) analogues, Was confirmed by comparing the C-13 NMR shifts of model compounds with those of the corresponding polymer. Poly(ene)s that are virtually solely based on six-membered repeat units show a bathochromic shift in UV-absorption compared to poly(ene)s based on six- and seven-membered rings.