1-hydroxynonan-4-one | 107841-11-2

• 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: 1-hydroxynonan-4-one
• CAS: 107841-11-2
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: DSRRWSQXJRQZMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  1-hydroxynonan-4-one 在 草酰氯 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (E)-1-phenylundec-2-ene-1,6-dione
  参考文献：
  名称：

  Structure–activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure

  摘要：

  In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro antimalarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.051
• 作为产物：
  描述：

  (E)-4-phenylsulfanylnon-4-en-1-ol 以70%的产率得到
  参考文献：
  名称：

  Matsumoto Kozo, Yokoo Toshiaki, Oshima Koichiro, Utimoto Kiitiro, Abd. Ra+, Bull. Chem. Soc. Jap, 67 (1994) N 6, S 1694-1700

  摘要：

  DOI：

文献信息

• Hg(OTf)2-Catalyzed Instantaneous Hydration of β- and δ-Hydroxy Internal Alkynes with Complete Regioselectivity
  作者：Mugio Nishizawa、Takayuki Takemoto、Ikuo Sasaki、Mayo Nakano、Elisabeth Ho、Kosuke Namba、Hirofumi Yamamoto、Hiroshi Imagawa

  DOI：10.1055/s-0028-1088153

  日期：2009.4

  The hydration of β- and δ-hydroxy internal alkynes catalyzed by Hg(OTf)2 took place instantaneously to give ketones with complete regioselectivity under mild conditions, whereas the hydration of internal alkyne without hydroxy moiety was very slow and gave a mixture of ketones. If the hydroxy group is located more than five carbons from the triple bond it has no significant effect upon the hydration reaction.

  在温和条件下，通过Hg(OTf)2催化的β-和δ-羟基内炔的水合反应可以瞬间完成，并且具有完全的区域选择性，生成酮类化合物，而没有羟基的内炔的水合反应则非常缓慢，且生成酮的混合物。如果羟基距离三键超过五个碳原子，那么它对水合反应几乎没有显著影响。
• 2,2-Dimethyl-1,3-oxathiane 3,3-Dioxide: A γ-Hydroxypropyl Anion Equivalent
  作者：Kaoru Fuji、Yoshihide Usami、Yoshimitsu Kiryu、Manabu Node

  DOI：10.1055/s-1992-26246

  日期：——

  The reaction of 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2, 2-dimethyl-1,3-oxathiane 3,3-dioxides which underwent desulfonation with silica gel to produce γ-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide was shown to be a useful synthetic equivalent of a γ-hydroxypropyl anion. Methyl esters proved to be the best acylating agents in this reaction. Synthetic utility of this carbon chain elongation was illustrated by the syntheses of dl-lanceol and dl-dihydrojasmone.

  4-锂-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物与各种电亲体的反应结果被呈现。对阴离子的酰化提供了不稳定的4-酰基-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物，这些化合物与硅胶脱磺反应，生成了具有三个碳单位延长的γ-羟基酮。因此，4-锂-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物被证明是一种有用的γ-羟基丙基阴离子的合成等价物。甲基酯在这个反应中被证明是最佳的酰化试剂。这种碳链延长的合成实用性通过合成dl-兰索尔和dl-二氢茉莉酮得到了说明。
• A new method for the preparation of γ-hydroxy ketones: a formal total synthesis of (±)-lanceol
  作者：Kaoru Fuji、Manabu Node、Yoshihide Usami、Yoshimitsu Kiryu

  DOI：10.1039/c39870000449

  日期：——

  The reaction of methyl esters with 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide followed by treatment with silica gel affords γ-hydroxy ketones.

  甲酯与2,2-二甲基-4-硫代-1,3-氧杂蒽3,3-二氧化物反应，然后用硅胶处理，得到γ-羟基酮。
• THE REACTION OF 2,2-DIMETHYL-4-LITHIO-1,3-OXATHIANE 3,3-DIOXIDE. GENERAL SYNTHESIS OF γ-HYDROXYKETONES
  作者：Kaoru Fuji、Manabu Node、Yoshihide Usami

  DOI：10.1246/cl.1986.961

  日期：1986.6.5

  Reactions of 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide (2) with alkyl halides and carbonyl compounds proceed smoothly to give 4-substituted heterocycles. A general synthesis of γ-hydroxyketones from aldehydes utilizing 2 is described.

  2,2-二甲基-4-锂-1,3-氧杂噻烷3,3-二氧化物(2)与卤代烷和羰基化合物的反应顺利进行，得到4-取代的杂环。描述了利用 2 从醛合成 γ-羟基酮的一般方法。
• Organoiridium Complexes Enhance Cellular Defense Against Reactive Aldehydes Species
  作者：Rahul D. Jana、Anh H. Ngo、Sohini Bose、Loi H. Do

  DOI：10.1002/chem.202300842

  日期：2023.6.27

  Although reactive aldehyde species (RASP) are associated with the pathogenesis of many major diseases, there are currently no clinically approved treatments for RASP overload. Conventional aldehyde detox agents are stoichiometric reactants that get consumed upon reacting with their biological targets, which limits their therapeutic efficiency. To achieve longer‐lasting detoxification effects, small‐molecule intracellular metal catalysts (SIMCats) were used to protect cells by converting RASP into non‐toxic alcohols. It was shown that SIMCats were significantly more effective in lowering cell death from the treatment with 4‐hydroxynon‐2‐enal than aldehyde scavengers over a 72 h period. Studies revealed that SIMCats reduced the aldehyde accumulation in cells exposed to the known RASP inducer arsenic trioxide. This work demonstrates that SIMCats offer unique benefits over stochiometric agents, potentially providing new ways to combat diseases with greater selectivity and efficiency than existing approaches.

  摘要尽管活性醛类（RASP）与许多重大疾病的发病机制有关，但目前还没有临床批准的治疗 RASP 超载的方法。传统的醛类解毒剂是化学计量反应物，与生物靶标发生反应后就会被消耗掉，这限制了它们的治疗效率。为了达到更持久的解毒效果，研究人员使用了小分子细胞内金属催化剂（SIMCats），通过将 RASP 转化为无毒的醇类来保护细胞。研究表明，在 72 小时内，SIMCats 在降低细胞因 4-hydroxynon-2-enal 处理而死亡方面的效果明显优于醛清除剂。研究表明，SIMCats 能减少暴露于已知 RASP 诱导剂三氧化二砷的细胞中的醛积累。这项工作表明，SIMCats 比测熵剂具有独特的优势，有可能提供比现有方法更具选择性和效率的新方法来防治疾病。