2,2,3,6,7,7-hexamethyl-oct-4-yne-3,6-diol | 89762-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,3,6,7,7-hexamethyl-oct-4-yne-3,6-diol
• 英文别名: 2,2,3,6,7,7-Hexamethyl-oct-4-in-3,6-diol；rac-1,4-Dimethyl-1,4-dipseudobutyl-butin-(2)-diol-(1,4)；1,4-Dimethyl-1,4-dipseudobutyl-butin-(2)-diol-(1,4)；4-Octyne-3,6-diol, 2,2,3,6,7,7-hexamethyl-；2,2,3,6,7,7-hexamethyloct-4-yne-3,6-diol
• CAS: 89762-84-5
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: QDCJURCJXBBNBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  2,2,3,6,7,7-hexamethyl-oct-4-yne-3,6-diol 在 三溴化磷 作用下， 生成 3,6-Dibromo-2,2,3,6,7,7-hexamethyl-oct-4-yne
  参考文献：
  名称：

  SYNTHESIS OF SUBSTITUTED BUTATRIENES AND NOVEL STRUCTURES OF THEIR O₂-OXIDATION PRODUCTS

  摘要：

  介绍了三种 2,3-二碘-1,3-二烯的合成以及将这些二烯转化为丁三烯的过程。2,5-二甲基六-2,3,4-三烯在暴露于空气中时发生聚合，生成聚合过氧化物 (C6H12O2)n，该过氧化物被重新分配为包含乙炔和过氧化物单元的结构。

  DOI：

  10.1246/cl.1984.131
• 作为产物：
  描述：

  acetylene-bis-magnesium bromide 、 频哪酮 在 乙醚 作用下， 生成 2,2,3,6,7,7-hexamethyl-oct-4-yne-3,6-diol
  参考文献：
  名称：

  Gwerdziteli; Mikadse, Sb. Statei Obshch. Khim., 1953, p. 960

  摘要：

  DOI：

文献信息

• (8-Naphthalen-1-ylmethyl-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-yl)-acetic acid methyl ester (NNC 63-0532) is a novel potent nociceptin receptor agonist
  作者：Christian Thomsen、Rolf Hohlweg

  DOI：10.1038/sj.bjp.0703661

  日期：2000.11

  Spiroxatrine was identified as a moderately potent (Ki=118 nM) but non‐selective agonist at the human nociceptin/orphanin FQ receptor, ORL1. This compound was subject to chemical modification and one of the resulting compounds, (8‐naphthalen‐1‐ylmethyl‐4‐oxo‐1‐phenyl‐1,3,8‐triaza‐spiro[4.5]dec‐3‐yl)‐acetic acid methyl ester (NNC 63‐0532) was shown to have high affinity for ORL1 (Ki=7.3 nM). NNC 63‐0532 showed only moderate affinity for the following receptors (Ki values in parentheses): μ‐opioid (140 nM), κ‐opioid (405 nM), dopamine D2S (209 nM), dopamine D3 (133 nM) and dopamine D4.4 (107 nM) out of 75 different receptors, ion‐channels and transporters. In functional assays, NNC 63‐0532 was shown to be an agonist at ORL1 (EC50=305 nM), a much weaker agonist at the μ‐opioid receptor (EC50>10 μM) and an antagonist or weak partial agonist at dopamine D2S (IC50=2830 nM). Thus, NNC 63‐0532 is a novel non‐peptide agonist with ∼12 fold selectivity for ORL1 and may be useful for exploring the physiological roles of this receptor owing to its brain‐penetrating properties. British Journal of Pharmacology (2000) 131, 903–908; doi:10.1038/sj.bjp.0703661

  Spiroxatrine被鉴定为一种中等效力的( Ki = 118 nM)且非选择性的nociceptin/orphanin FQ受体（ORL1）激动剂。该化合物进行了化学修饰，其中一种产物，(8-naphthalen-1-ylmethyl-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dEC-3-yl)-acetic acid methyl ester（NNC 63-0532）显示出对ORL1的高亲和力（Ki = 7.3 nM）。 NNC 63-0532仅对以下受体显示出中等亲和力（括号中的Ki值）：μ-阿片受体（140 nM），κ-阿片受体（405 nM），多巴胺D2S（209 nM），多巴胺D3（133 nM）和多巴胺D4.4（107 nM），在总共75种不同的受体、离子通道和转运体中。 在功能测定中，NNC 63-0532被证明是对ORL1的激动剂（EC50 = 305 nM），是对μ-阿片受体的较弱激动剂（EC50 > 10 μM），而对多巴胺D2S则是拮抗剂或弱的部分激动剂（IC50 = 2830 nM）。 因此，NNC 63-0532是一种新型的非肽类激动剂，对ORL1的选择性约为12倍，因其具有穿透脑的能力，可能有助于探索该受体的生理作用。 British Journal of Pharmacology (2000) 131, 903–908; doi:10.1038/sj.bjp.0703661
• Jozitsch, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1902, vol. 34, p. 243
  作者：Jozitsch

  DOI：——

  日期：——
• Sung, Annales de Chimie (Cachan, France), 1924, vol. <10>1, p. 364
  作者：Sung

  DOI：——

  日期：——
• Comparative phytotoxicity of four monoterpenes against Cassia occidentalis
  作者：H P SINGH、DAIZY R BATISH、S KAUR、H RAMEZANI、R K KOHLI

  DOI：10.1111/j.1744-7348.2002.tb00202.x

  日期：2002.10

  SummaryThe effect of four monoterpenes ‐ citronellol, citronellal, cineole and linalool ‐ on the germination, growth and physiology of Cassia occidentalis was investigated. All four monoterpenes reduced germination of C. occidentalis seeds but to varying extents. Citronellal and linalool completely inhibited germination beyond the concentrations of 55 and 110 μM, respectively, whereas in response to treatment of citronellol no germination was observed beyond 330 μM. Further, the growth of seedlings, measured in terms of seedling length and biomass, was also adversely affected. A reduction in chlorophyll content of the cotyledonary leaves of C. occidentalis was also noticed, indicating an adverse effect on photosynthesis. Likewise, respiratory ability of growing seeds was also impaired in response to all four monoterpenes, clearly indicating that monoterpenes affect energy metabolism. On the basis of overall phytotoxicity, potency of monoterpenes was in the order of citronellal > linalool > citronellol > cineole. The results from this study suggest that both citronellal and linalool possess strong phytotoxic potential and can thus serve as lead molecules for the synthesis of bioherbicides.
• Rupe; Giesler, Helvetica Chimica Acta, 1928, vol. 11, p. 666
  作者：Rupe、Giesler

  DOI：——

  日期：——