dimethyl 5-oxononanedioate | 36596-53-9

• 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: dimethyl 5-oxononanedioate
• CAS: 36596-53-9
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: YSUOGWANLOPQRT-UHFFFAOYSA-N

物化性质

• 熔点：
  33-34 °C
• 沸点：
  318.5±17.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 5-oxononanedioate 在 manganese(IV) oxide 、 iron(III) chloride 、 sodium hypochlorite 、 Hoveyda-Grubbs catalyst second generation 、 2,2,6,6-四甲基哌啶氧化物 、 偶氮二异丁腈 、 异丙氧基三甲基硅烷 、 三氟甲磺酸三甲基硅酯 、 三(三甲基硅基)硅烷 、 氨 、 silica gel 、 lithium 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 potassium tri-sec-butyl-borohydride 、 potassium bromide 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 98.0h， 生成
  参考文献：
  名称：

  通过立体选择性自由基易位-环化反应的全合成（-）-Histrionicotoxin

  摘要：

  描述了（-）-histrionicotoxin和（-）-histrionicotoxin 235A的立体选择性全合成。1-azaspiro [5.5]十一烷骨架是通过涉及手性环缩醛的自由基易位环化反应非对映选择性地构建的；三（三甲基甲硅烷基）硅烷的使用对于高非对映选择性至关重要。通过含未保护内酰胺的衍生物的一锅部分还原烯丙基化反应，环化产物转化为（-）-histrionicotoxin 235A。最后，将两个末端烯烃转化为烯炔，并以1,3-氨基醇作为氧杂噻唑烷氧化物进行保护，以完成（-）-组蛋白毒素的全部合成。

  DOI：

  10.1002/anie.201609941
• 作为产物：
  描述：

  4-氯甲酰基丁酸甲酯 在 diiron nonacarbonyl 作用下， 生成 dimethyl 5-oxononanedioate
  参考文献：
  名称：

  酰基羰基二铁和羰基镍络合物偶合酰氯。对称的伯烷基酮的制备。

  摘要：

  DOI：

  10.1016/s0040-4039(01)83374-8

文献信息

• [EN] IONIZABLE AMINE LIPIDS AND LIPID NANOPARTICLES<br/>[FR] LIPIDES AMINÉS IONISABLES ET NANOPARTICULES LIPIDIQUES
  申请人：BEAM THERAPEUTICS INC

  公开号：WO2023121975A1

  公开（公告）日：2023-06-29

  The present disclosure describes compositions, preparations, nanoparticles (such as lipid nanoparticles), and/or nanomaterials and methods of their use.

  本公开介绍了组合物、制剂、纳米颗粒（如脂质纳米颗粒）和/或纳米材料及其使用方法。
• Design, Synthesis, Anti-HIV Activities, and Metabolic Stabilities of Alkenyldiarylmethane (ADAM) Non-nucleoside Reverse Transcriptase Inhibitors
  作者：Maximilian A. Silvestri、Muthukaman Nagarajan、Erik De Clercq、Christophe Pannecouque、Mark Cushman

  DOI：10.1021/jm049916x

  日期：2004.6.1

  The alkenyldiarylmethane (ADAM) HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) are effective anti-HIV agents in cell culture. However, the potential clinical utility of the ADAMs is expected to be limited by the presence of methyl ester moieties that are likely to be metabolized by nonspecific esterases in blood plasma to biologically inactive carboxylic acid derivatives. The present investigation was therefore undertaken to investigate the anti-HIV activities of the ADAMs versus HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells and the stabilities of the biologically active ADAMs in rat plasma. The ADAMs displayed a wide range of metabolic stabilities in rat plasma, with half-lives ranging from 0.9 to 76.6 min. A wide assortment of structural modifications was tolerated, with 18 of the 32 compounds tested displaying EC50 values between 0.3 and 3.7 muM versus HIV-1(IIIB) in MT-4 cells, 3 compounds in the EC50 = 13.2-35.4 muM range, and the remaining compounds inactive. Consistent with the mechanism of action of the ADAMs as NNRTIs, they were inactive or displayed comparatively low activity versus HIV-2ROD. The replacement of the two aromatic methyl ester substituents in one of the most active ADAMs (EC50 = 0.6 muM) with two methyl thioester groups resulted in an increase in plasma half-life from 5.8 to 55.3 min, while maintaining the antiviral potency at the EC50 = 1.8 muM level. At the same time, the bis(thioester) modification was less cytotoxic to uninfected MT-4 cells, with a CC50 of >224 muM versus 160 muM for the parent compound.
• v. Pechmann; Sidgwick, Chemische Berichte, 1904, vol. 37, p. 3819
  作者：v. Pechmann、Sidgwick

  DOI：——

  日期：——
• Synthesis of canthine/erythrinane alkaloid analogs
  作者：Josef Hájíček、Jan Trojánek

  DOI：10.1007/bf00798289

  日期：1985.1
• Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C
  作者：Mercedes Amat、Rosa Griera、Robert Fabregat、Joan Bosch

  DOI：10.1016/j.tetasy.2008.04.022

  日期：2008.5

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.