(R)-2-methyloctanoic acid

• 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: (R)-2-methyloctanoic acid
• 英文别名: (2~{R})-2-methyloctanoic acid；(2R)-2-methyloctanoic acid
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: YSEQNZOXHCKLOG-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (R)-2-methyloctanoic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以81%的产率得到(R)-2-methyloctan-1-ol
  参考文献：
  名称：

  Probing the Limits of the Majority-Rules Principle in a Dynamic Supramolecular Polymer

  摘要：

  By systematic variation of the chemical structure of benzene-1,3,5-tricarboxamide (BTA) derivatives, the effect of chemical structure on the amplification of chirality was studied and quantified. In combination with temperature-dependent amplification experiments, the limits of the majority-rules principle were also investigated. For all BTA derivatives a high, constant helix reversal penalty was determined, which is related to the intermolecular hydrogen bonds that are present in all studied derivatives. For asymmetrically substituted BTA derivatives an odd-even effect was found in the degree of chiral amplification when changing the position of the stereogenic center with respect to the amide functionality. It was found that the mismatch penalty could be directly related to the number of stereocenters present in the molecules. Increasing this number from one to three resulted in an increase in this energy penalty while leaving the helix reversal penalty unaffected. For the majority-rules principle this implies that a single stereocenter present in the molecule contains sufficient chiral information at the molecular level to result in a chirally amplified state at the supramolecular level. Further evidence that the mismatch penalty is directly related to the number of stereocenters was obtained from mixed majority-rules experiments where two BTA derivatives with different numbers of stereocenters with opposite stereoconfiguration were studied in a majority-rules experiment. Finally, the ultimate limits of chiral amplification for the majority-rules principle were investigated, revealing that, given a certain helix reversal penalty, there is an optimum to which the mismatch penalty can be reduced while also enhancing the degree of chiral amplification. Temperature-dependent majority-rules experiments could indeed confirm these simulations. These findings show the relevance of both energy penalties when trying to enhance the degree of chiral amplification for the majority-rules principle in a one-dimensional helical supramolecular polymer.

  DOI：

  10.1021/ja9080875
• 作为产物：
  描述：

  山梨酸 在 potassium permanganate 、 sodium periodate 、 氯化亚砜 、 copper(I) bromide dimethylsulfide complex 、 (R,S)-Josiphos 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 30.91h， 生成 (R)-2-methyloctanoic acid
  参考文献：
  名称：

  共轭二烯基酰胺的催化区域和对映选择性烷基化

  摘要：

  已开发出一种共轭二烯基酰胺催化不对称烷基化的方法，该方法可以将各种范围的聚共轭酰胺高效高效地转化为相应的手性产物。由于路易斯酸和手性铜基催化剂的互补作用，可以将有机镁试剂平稳地添加到具有极好的1,6和1,4,4选择性以及相对于90％以上的对映体的相对无反应性的二烯基酰胺中。

  DOI：

  10.1002/anie.201808392

文献信息

• Enantioselective Hydrogenation of α-Substituted Acrylic Acids Catalyzed by Iridium Complexes with Chiral Spiro Aminophosphine Ligands
  作者：Shou-Fei Zhu、Yan-Bo Yu、Shen Li、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1002/anie.201204363

  日期：2012.8.27

  Highly active: Iridium complexes with chiral spiro aminophosphine ligands were synthesized and applied as catalysts for the asymmetric hydrogenation of α‐substituted acrylic acids (see scheme). The complexes were highly active catalysts, showing turnover frequencies of up to 6000 h−1, and catalyst loadings could be reduced to 0.01 mol %.

  高活性：与手性螺环氨基膦配体的铱络合物的合成和作为催化剂用于α-取代的丙烯酸的不对称氢化（参见方案）施用。该复合物具有高活性的催化剂，显示出6000 h最多的周转频率-1，并且催化剂载量可减少到0.01％（摩尔）。
• Bifunctional Doscadenamides Activate Quorum Sensing in Gram-Negative Bacteria and Synergize with TRAIL to Induce Apoptosis in Cancer Cells
  作者：Xiao Liang、Qi-Yin Chen、Gustavo M. Seabra、Susan Matthew、Jason C. Kwan、Chenglong Li、Valerie J. Paul、Hendrik Luesch

  DOI：10.1021/acs.jnatprod.0c01003

  日期：2021.3.26

  sensing (QS) activator in Pseudomonas aeruginosa, characterized by dual acylation of the pyrrolinone core structure and the pendant side chain primary amine to form an imide/amide hybrid are reported. The identities of doscadenamides B–J were confirmed through total synthesis and a strategic focused library with different acylation and unsaturation patterns was created. Key molecular interactions for

  报道了源自蓝藻的新型双功能多卡登酰胺 A 类似物，多卡登酰胺 A 是铜绿假单胞菌中一种 LasR 依赖性群体感应 (QS) 激活剂，其特征是吡咯啉酮核心结构和侧链伯胺双酰化，形成酰亚胺/酰胺杂化物。通过全合成确认了多斯卡登酰胺 B–J 的特性，并创建了具有不同酰化和不饱和模式的战略重点库。通过突变研究和分子对接确定了与 LasR 结合的关键分子相互作用和功能反应。在包括铜绿假单胞菌和哈维氏弧菌在内的各种革兰氏阴性细菌中探讨了结构-活性关系（SAR），表明吡咯啉酮-N酰基链对于完全激动剂活性至关重要，而其他酰基链是可有可无的或可能导致拮抗剂活性，取决于细菌系统。由于高丝氨酸内酯 (HSL) 群体感应激活剂已被证明与 TRAIL 协同作用以诱导癌细胞凋亡，因此在正交真核筛选系统中测试了选定的多卡登酰胺。最有效的 QS 激动剂多卡登酰胺 S10-S12，以及酰基侧链部分或完全饱和的多卡登酰胺 F
• [EN] METHOD FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID<br/>[FR] METHODE SERVANT A PREPARER UN ACIDE CARBOXYLIQUE POSSEDANT UNE ACTIVITE OPTIQUE
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2004087632A1

  公开（公告）日：2004-10-14

  A method for producing a desired optically active carboxylic acid with a high optical purity, wherein a complex catalyst used can be recovered and reused as an aqueous solution. The method contains the step of subjecting an α,β-unsaturated carboxylic acid in water or a mixed solvent of water and a water-insoluble organic solvent in the presence of a sulfonated BINAP-Ru complex represented by the formula [3]: [RuX(arene)(SO?3#191M)?2#191-BINAP}]X [3]wherein X represents a chlorine atom, a bromine atom or an iodine atom, arene represents a benzene or an alkyl-substituted benzene,M represents an alkaline metal atom, and BINAP represents 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl to an asymmetric hydrogenation. The sulfonated BINAP-Ru complex can be recycled.

  一种用于生产具有高光学纯度的所需光学活性羧酸的方法，其中所使用的复合催化剂可以作为水溶液被回收和重复使用。该方法包括在水中或水和水不溶性有机溶剂的混合溶剂中，在存在由公式[3]表示的磺化BINAP-Ru复合物的情况下，使α，β-不饱和羧酸经历不对称氢化的步骤：[RuX(arene)(SO?3#191M)?2#191-BINAP}]X [3]，其中X代表氯原子、溴原子或碘原子，arene代表苯或烷基取代的苯，M代表碱金属原子，BINAP代表2,2'-联苯二膦基-1,1'-联萘基。磺化BINAP-Ru复合物可以回收利用。
• [EN] DISCOVERY, TOTAL SYNTHESIS, AND BIOACTIVITY OF DOSCADENAMIDES<br/>[FR] DÉCOUVERTE, SYNTHÈSE TOTALE ET BIOACTIVITÉ DE DOSCADENAMIDES
  申请人：UNIV FLORIDA

  公开号：WO2021021629A1

  公开（公告）日：2021-02-04

  The invention is directed towards compounds (e.g., Formulae (I)-(IX)), their mechanism of action, processes to prepare the compounds, methods of activating quorum sensing signaling activity, and methods of treating diseases and disorders using the compounds described herein (e.g., Formulae (I)-(IX)).

  这项发明涉及化合物（例如，式（I）-（IX）），它们的作用机制，制备这些化合物的方法，激活群体感应信号活性的方法，以及利用本文描述的化合物治疗疾病和疾病的方法（例如，式（I）-（IX））。
• A Synthetic Approach to Diverse 3-Acyltetramic Acids via <i>O</i>- to <i>C</i>-Acyl Rearrangement and Application to the Total Synthesis of Penicillenol Series
  作者：Tetsuya Sengoku、Yuta Nagae、Yasuaki Ujihara、Masaki Takahashi、Hidemi Yoda

  DOI：10.1021/jo300527f

  日期：2012.5.4

  efficient approach to medicinally important α-branched 3-acyltetramic acids, the key reaction of O- to C- acyl rearrangement using α-amino-acid-derived 4-O-acyltetramic acids was extensively examined in the presence of various metal salts. Use of CaCl2 or NaI dramatically changed the results in the reaction efficiency and rapidly brought about the desired α-branched 3-acyltetramic acids in markedly

  为了有效地利用具有重要医学意义的α-支链3-酰基四酸，在各种金属盐存在下，广泛研究了使用α-氨基酸衍生的4- O-酰基四酸对O-进行C酰基重排的关键反应。。CaCl 2或NaI的使用显着改变了反应效率的结果，并以显着提高的产率迅速产生了所需的α-支化的3-酰基四酸。我们还讨论了重排条件下C5立体中心的差向异构化以及C3和C5的结构变异耐受性。除了先前在成功合成新的细胞毒性四酸青霉素A 1方面的成功之外，，这种方法也可以应用于青霉素A 2的第一次全合成。