6-氧代-辛酸 | 4233-57-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 6-氧代-辛酸
• 中文别名: 6-氧代辛酸
• 英文名称: 6-oxooctanoic acid
• 英文别名: 6-Oxo-octanoic acid
• CAS: 4233-57-2
• 化学式: C₈H₁₄O₃
• mdl: MFCD01320160
• 分子量: 158.197
• InChiKey: PUOYTVHCFIDKJM-UHFFFAOYSA-N

物化性质

• 熔点：
  52 °C
• 沸点：
  311.1±25.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  6-氧代-辛酸 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 84.0h， 生成 N-(1'-(R)-phenyl-2'-hydroxyethyl)-2-(R)-ethylhexahydroazepine
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Alkyl-Perhydroazepines from [5,3,0]-Bicyclic Lactams

  摘要：

  The synthesis and utility of a novel class of [5,3,0]-bicyclic lactams are described. Produced by the cyclodehydration of (R)-phenylglycinol with omega -keto acids, lactams 4-6 were obtained as separable diastereomeric mixtures (similar to2:1) in low yields (similar to 40%). Higher chemical yield (up to 61%) was realized tia an alternate route involving ring closure metathesis of 2-allyl-N-acroyl oxazolidines, 8. Stereoselective reductions of the syn-bicyclic lactams, 4a and 5a, occurred with the use of alane or lithiumaluminum hydride, affording azepine alcohols, 11a and;15a, of the R configuration at the 2-position, in good to moderate yields (50-88%). High selectivity was also observed in the diisobutylaluminum hydride reduction of the epimeric anti lactams, 4b and 5b, affording azepine alcohols, 11b and 15b, of the S configuration at C-2. Hydrogenolytic cleavage of the N-benzyl moiety afforded chiral 2-substituted perhydroazepines, (R)- and (S)-12, in good yields and good enantiomeric excesses (84-94%).

  DOI：

  10.1021/jo001548r
• 作为产物：
  描述：

  2-乙基环己酮 在 cerium(IV) sulphate 、 氧气 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以85%的产率得到6-氧代-辛酸
  参考文献：
  名称：

  在醇和乙酸中用四水硫酸铈 (IV) 氧化 2-取代的环烷酮

  摘要：

  2-取代环烷酮与四水合硫酸铈 (CS) 在醇和乙酸中反应，分别通过氧化反应生成相应的含氧酸 (80-96%) 和含氧酸 (78-​​96%) 烷基酯C(R)–C=O 键的断裂。在甲醇中的 2-碘环烷酮的情况下，以良好的收率获得二甲酯。在甲醇中用 CS 处理 5α-cholestan-3-one 以良好的收率产生 2,3-seco 衍生物的 2-缩醛 3-酯。还讨论了铈 (IV) 和铜 (II) 盐的影响。

  DOI：

  10.1246/bcsj.72.2515

文献信息

• Selective C–C Bond Cleavage of Cycloalkanones by NaNO₂/HCl
  作者：Tianyu He、Dengfeng Chen、Shencheng Qian、Yu Zheng、Shenlin Huang

  DOI：10.1021/acs.orglett.1c02327

  日期：2021.8.20

  A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C–C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

  建立了一种新型的 NaNO 2 /HCl选择性裂解环烷酮的方法。C-C 键裂解反应在温和条件下顺利进行，选择性地提供通用的酮酸或肟酸。该方法可以简化从现成的原料中合成有价值的手性分子和异香豆素的过程。
• [EN] GRANZYME B INHIBITOR FORMULATIONS AND METHODS FOR THE TREATMENT OF BURNS<br/>[FR] FORMULATIONS INHIBITRICES DE GRANZYME B ET MÉTHODES DE TRAITEMENT DE BRÛLURES
  申请人：VIDA THERAPEUTICS INC

  公开号：WO2017132771A1

  公开（公告）日：2017-08-10

  Formulations for treating burns and burn wound healing comprising a Granzyme B inhibitor and a pharmaceutically acceptable carrier, and methods for treating burns and for burn wound healing using the formulations.

  治疗烧伤和烧伤愈合的配方包括一种Granzyme B抑制剂和一种药用可接受载体，以及使用这些配方进行治疗烧伤和烧伤愈合的方法。
• Direct and chemoselective conversion of carboxylic acids into aldehydes
  作者：Tamotsu Fujisawa、Toshiki Mori、Shoichi Tsuge、Toshio Sato

  DOI：10.1016/s0040-4039(00)81704-9

  日期：——

  A new method for the direct conversion of carboxylic acids to aldehydes using N,N-dimethylchloromethyleniminium chloride and lithium tri-t-butoxyaluminum hydride was established. This method provides a convenient way for the chemoselective reduction of carboxylic acids even with such a functional group as halide, ester, nitrile, olefin, and ketone.

  建立了一种使用N，N-二甲基氯甲基亚氯化铵和氢化三叔丁氧基铝锂将羧酸直接转化为醛的新方法。该方法提供了即使具有诸如卤化物，酯，腈，烯烃和酮之类的官能团也可用于化学选择还原羧酸的简便方法。
• HIGHLY CHEMOSELECTIVE SYNTHESIS OF KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS USING α-CHLOROENAMINES AS A CONDENSATION REAGENT
  作者：Tamotsu Fujisawa、Toshiki Mori、Kazunobu Higuchi、Toshio Sato

  DOI：10.1246/cl.1983.1791

  日期：1983.11.5

  α-Chloroenamines are found to be an effective condensation reagent of carboxylic acids and Grignard reagents under mild conditions to afford chemoselectively the corresponding ketones in high yields and in one-pot operation.

  α-氯烯胺被发现是一种有效的羧酸和格氏试剂在温和条件下的缩合试剂，以高产率和一锅法化学选择性地提供相应的酮。
• One-pot room-temperature conversion of cyclohexane to adipic acid by ozone and UV light
  作者：Kuo Chu Hwang、Arunachalam Sagadevan

  DOI：10.1126/science.1259684

  日期：2014.12.19

  Nitric acid oxidation of cyclohexane accounts for ~95% of the worldwide adipic acid production and is also responsible for ~5 to 8% of the annual worldwide anthropogenic emission of the ozone-depleting greenhouse gas nitrous oxide (N ₂ O). Here we report a N ₂ O-free process for adipic acid synthesis. Treatment of neat cyclohexane, cyclohexanol, or cyclohexanone with ozone at room temperature and 1 atmosphere of pressure affords adipic acid as a solid precipitate. Addition of acidic water or exposure to ultraviolet (UV) light irradiation (or a combination of both) dramatically enhances the oxidative conversion of cyclohexane to adipic acid.

  环己烷的硝酸氧化占全球己二酸产量的约95％，也占全球年人为排放的臭氧层破坏温室气体一氧化二氮（N2O）的5％至8％。我们报道了一种无N2O的己二酸合成工艺。在室温和1大气压下，对纯环己烷、环己醇或环己酮进行臭氧处理，生成己二酸作为固体沉淀。加入酸性水或暴露于紫外（UV）光照射（或两者结合）显著增强了环己烷氧化转化为己二酸。