7-(benzyloxy)heptanoic acid | 124267-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(benzyloxy)heptanoic acid
• 英文别名: 7-Benzyloxyheptanoic acid；7-phenylmethoxyheptanoic acid
• CAS: 124267-23-8
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: AHSCDCVZBOWTAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)heptanoic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 氢气 、 双氧水 、 sodium hexamethyldisilazane 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 62.25h， 生成 (S)-2-[Methyl-((S)-3-methyl-2-{methyl-[(S)-3-methyl-2-(methyl-{(S)-3-methyl-2-[methyl-((R)-2-methyl-oct-7-ynoyl)-amino]-butyryl}-amino)-butyryl]-amino}-butyryl)-amino]-3-phenyl-propionic acid tert-butyl ester
  参考文献：
  名称：

  龙酰胺的立体化学的全合成与重分配

  摘要：

  据报道，首次合成了龙酰胺。合成导致该分子的带有炔的片段上的立体中心的构型重新分配。

  DOI：

  10.1016/j.tet.2005.09.040
• 作为产物：
  描述：

  1,7-庚二醇 在 Jones reagent 、 silver(l) oxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 15.5h， 生成 7-(benzyloxy)heptanoic acid
  参考文献：
  名称：

  Enhanced Spacer Length between Mannose Mimicking Shikimoyl and Quinoyl Headgroups and Hydrophobic Region of Cationic Amphiphile Increases Efficiency of Dendritic Cell Based DNA Vaccination: A Structure–Activity Investigation

  摘要：

  In the field of dendritic cell based genetic immunization, previously we showed that liposomes of cationic amphiphiles containing mannose-mimicking shikimoyl headgroup are promising DNA vaccine carriers for dendritic cell (DC) transfection. The present structure activity study reports on the influence of spacer length (between mannose-mimicking headgroups and quaternary nitrogen centers) in modulating the DC-transfection efficiencies. Further, we report on the anti melanoma immune response inducing properties of the promising cationic amphiphiles in syngeneic CS7BL/6J mice under prophylactic settings.

  DOI：

  10.1021/acs.jmedchem.6b01556

文献信息

• Nickel-Catalyzed Carboxylation of Organozinc Reagents with CO₂
  作者：Hidenori Ochiai、Minsul Jang、Koji Hirano、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol800764u

  日期：2008.7.3

  An efficient nickel catalyst system for the carboxylation of organozinc reagents with CO(2) under very mild conditions has been developed. The catalyst system complements the conventional methods and enables the direct synthesis of various saturated carboxylic acid derivatives from the corresponding alkylzinc reagents and CO(2).

  已经开发了一种在非常温和的条件下将有机锌试剂与CO（2）羧化的有效镍催化剂体系。该催化剂体系是对常规方法的补充，可以从相应的烷基锌试剂和CO（2）直接合成各种饱和羧酸衍生物。
• Palladium-Catalyzed C(sp³)–H Nitrooxylation with <i>tert</i>-Butyl Nitrite and Molecular Oxygen
  作者：Bo Li、Ye-Qiang Han、Xu Yang、Bing-Feng Shi

  DOI：10.1021/acs.orglett.0c03794

  日期：2020.12.18

  Herein, we report a Pd(II)-catalyzed nitrooxylation of unactivated methyl C(sp3)–H bonds using commercial available and easily manageable tert-butyl nitrite as the precursor of ONO2 radical under aerobic conditions. Environmentally benign molecular oxygen is used to initiate the generation of active radical reactant; it is also used as the terminal oxidant. A broad range of nitrooxylated aliphatic

  在这里，我们报告了P​​d（II）催化未活化的甲基C（sp 3）-H键的Pd（II）硝基氧化，使用有氧条件下可商购获得且易于操作的亚硝酸叔丁酯作为ONO 2自由基的前体。使用环境无害的分子氧来引发活性自由基反应物的产生。它也用作末端氧化剂。在温和的条件下，以中等至良好的收率制备了多种硝基氧化脂肪族羧酰胺。
• Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO₂
  作者：Marino Börjesson、Toni Moragas、Ruben Martin

  DOI：10.1021/jacs.6b04088

  日期：2016.6.22

  A catalytic carboxylation of unactivated primary, secondary, and tertiary alkyl chlorides with CO2 at atmospheric pressure is described. This protocol represents the first intermolecular cross-electrophile coupling of unactivated alkyl chlorides, thus leading to new knowledge in the cross-coupling arena.

  描述了未活化的伯、仲和叔烷基氯化物在大气压下与 CO2 的催化羧化。该协议代表了未活化烷基氯化物的第一个分子间交叉亲电偶联，从而导致交叉偶联领域的新知识。
• Composition and its use for imparting water repellency to leather or furskins, textiles and other fibrous materials
  申请人：Eigen Peter

  公开号：US20050148702A1

  公开（公告）日：2005-07-07

  Compositions comprising a mineral oil or wax and a liquid polysiloxane substituted by functional groups, an anionic surfactant and additionally a molecular mono- or polycarboxylic acid and optionally any emulsifiable, hydrophilic or amphiphilic polymer comprising carboxyl groups are outstanding water repellents for leather, furskins, textiles and fibrous materials.

  由矿物油或蜡和被官能团取代的液态聚硅氧烷、阴离子表面活性剂以及单羧酸或多羧酸分子和可选的包含羧基的任何可乳化的亲水或两性聚合物组成的复合物是皮革、毛皮、纺织品和纤维材料的出色防水剂。
• Inhibition of Matrix Metalloproteinases by Hydroxamates Containing Heteroatom-Based Modifications of the P1' Group
  作者：Madhusudhan R. Gowravaram、Jeffrey S. Johnson、Daniel Delecki、Ewell R. Cook、Bruce E. Tomczuk、Arup K. Ghose、Alan M. Mathiowetz、John C. Spurlino、Byron Rubin、Douglas L. Smith、Tricia Pulvino、Robert C. Wahl

  DOI：10.1021/jm00014a010

  日期：1995.7

  In this study, structure-based drug design of matrix metalloproteinase inhibitors [human fibroblast collagenase (HFC), human fibroblast stromelysin (HFS), and human neutrophil collagenase (HNC)] was utilized in the development of potent hydroxamates which contain novel, heteroatom-based modifications of the P-1' group. A series containing a P-1' butyramide group resulted in a nanomolar potent and selective HNC inhibitor as well as a dual HFS/HNC inhibitor. Benzylic others with a four- or five-carbon methylene linker in the P-1' position also produced nanomolar potent HFS/HNC inhibition and micromolar potent HFC inhibition as expected. Surprisingly, the phenolic ethers of the same overall length as the benzylic ethers showed nanomolar potencies against HFC, as well as HFS and HNC. The potency profile of the phenolic ethers was optimized by structure-activity relationships of the phenolic group and the C-terminal amide. These inhibitors may help elucidate the in vivo roles of matrix metalloproteinases in normal and disease states.