3-hydroxy-5,9-dimethyl-dec-8-en-2-one | 367522-58-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-hydroxy-5,9-dimethyl-dec-8-en-2-one
• 英文别名: 3-hydroxy-5,9-dimethyldec-8-en-2-one
• CAS: 367522-58-5
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: MSHLNKCUNGPTTI-UHFFFAOYSA-N

物化性质

• 沸点：
  310.0±30.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5,9-dimethyl-dec-8-en-2-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以150 mg的产率得到5,9-dimethyl-8-decene-2,3-dione
  参考文献：
  名称：

  Inactivation of Protein Farnesyltransferase by Active-Site-Targeted Dicarbonyl Compounds

  摘要：

  Upon farnesylation by protein farnesyltransferase (FTase), key proteins become compartmentalized in cells. For example, cell membrane localization is essential for the mitogenic role of mutant Ras protein, which acts as a switch for cancer cell proliferation. We repel? that alpha -dicarbonyl compounds derived from the isoprenoid skeleton or other hydrophobic groups potently obstruct farnesylation of a Ras model peptide by human recombinant FTase in vitro. A geranyl-derived isoprenoid diketone, 5.9-dimethyl-8-decene-2,3-dione, at 17 muM caused a 62% reduction in FTase activity after 30 minutes. A farnesyl-derived isoprenoid diketone, 5,9,13-trimethyl-8,12-tetradecadiene-2,3-dione, at 93 muM caused a 94% reduction after 30 minutes. Other dicarbonyl:compounds found to be effective against FTase in vitro were (+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid, 4,4 ' -biphenyldiglyoxaldehyde, dehydroascorbic acid 6-palmitace, 2-oxododecanal, and phenylglyoxal. Higher concentrations of the alpha -dicarbonyl compound resulted in more rapid and more extensive inactivation. These findings demonstrate that ct-dicarbonyl compounds targeted to FTase interfere with protein farnesylation in vitro and may,lead to derivatives that have utility as chemotherapeutic agents.

  DOI：

  10.1002/1521-4184(200106)334:6<194::aid-ardp194>3.0.co;2-m
• 作为产物：
  描述：

  香茅醛 在 三乙胺 、 copper(I) bromide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-hydroxy-5,9-dimethyl-dec-8-en-2-one
  参考文献：
  名称：

  萜烯醛合成α-羟基酮

  摘要：

  摘要 从市售的萜醛合成了分子内具有类异戊二烯单元的不对称取代的 α-羟基酮。该合成适用于α,β-不饱和醛，并以总体良好的收率提供相应的α-羟甲基酮。这些产物的互变异构在反应条件下不发生，但在加热时观察到。非对映异构 α-羟基酮已被解析，对这些类似物之一的 X 射线分析允许阐明转化为其莰酸酯后的立体化学。

  DOI：

  10.1081/scc-200025618

文献信息

• US7344851B2
  申请人：——

  公开号：US7344851B2

  公开（公告）日：2008-03-18
• Synthesis of α‐Hydroxy Ketones from Terpene Aldehydes
  作者：Martin Schueler、Holger Zorn、Alexandra M. Z. Slawin、Ralf G. Berger

  DOI：10.1081/scc-200025618

  日期：2004.1.1

  reaction but was observed upon heating. Diastereoisomeric α‐hydroxy ketones have been resolved, and X‐ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

  摘要 从市售的萜醛合成了分子内具有类异戊二烯单元的不对称取代的 α-羟基酮。该合成适用于α,β-不饱和醛，并以总体良好的收率提供相应的α-羟甲基酮。这些产物的互变异构在反应条件下不发生，但在加热时观察到。非对映异构 α-羟基酮已被解析，对这些类似物之一的 X 射线分析允许阐明转化为其莰酸酯后的立体化学。
• Inactivation of Protein Farnesyltransferase by Active-Site-Targeted Dicarbonyl Compounds
  作者：Karl J. Okolotowicz、Wei-Jen Lee、Rosemarie F. Hartman、Ann Y. Kim、Steven R. Ottersberg、Dale E. Robinson, Jr.、Scott R. Lefler、Seth D. Rose

  DOI：10.1002/1521-4184(200106)334:6<194::aid-ardp194>3.0.co;2-m

  日期：2001.6

  Upon farnesylation by protein farnesyltransferase (FTase), key proteins become compartmentalized in cells. For example, cell membrane localization is essential for the mitogenic role of mutant Ras protein, which acts as a switch for cancer cell proliferation. We repel? that alpha -dicarbonyl compounds derived from the isoprenoid skeleton or other hydrophobic groups potently obstruct farnesylation of a Ras model peptide by human recombinant FTase in vitro. A geranyl-derived isoprenoid diketone, 5.9-dimethyl-8-decene-2,3-dione, at 17 muM caused a 62% reduction in FTase activity after 30 minutes. A farnesyl-derived isoprenoid diketone, 5,9,13-trimethyl-8,12-tetradecadiene-2,3-dione, at 93 muM caused a 94% reduction after 30 minutes. Other dicarbonyl:compounds found to be effective against FTase in vitro were (+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid, 4,4 ' -biphenyldiglyoxaldehyde, dehydroascorbic acid 6-palmitace, 2-oxododecanal, and phenylglyoxal. Higher concentrations of the alpha -dicarbonyl compound resulted in more rapid and more extensive inactivation. These findings demonstrate that ct-dicarbonyl compounds targeted to FTase interfere with protein farnesylation in vitro and may,lead to derivatives that have utility as chemotherapeutic agents.