methyl (R)-3-hydroxynonanoate | 28941-56-2

• 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: methyl (R)-3-hydroxynonanoate
• 英文别名: Methyl (3r)-3-hydroxynonanoate
• CAS: 28941-56-2
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: KHCQOQFCKCGHHU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  methyl (R)-3-hydroxynonanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以80%的产率得到(R)-(-)-1,3-壬烷二醇
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2
• 作为产物：
  描述：

  (R)-(-)-3-羟基壬醛二甲基缩醛 在 盐酸 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 以49%的产率得到methyl (R)-3-hydroxynonanoate
  参考文献：
  名称：

  蓖麻油酸和3-羟基壬酸的手性酰胺衍生物的合成及细胞毒活性

  摘要：

  在这项研究中，使用各种化学和生化方法合成了一系列手性蓖麻油酸和3-羟基壬酸衍生物。提出了一种通过臭氧分解和氧化从蓖麻油或蓖麻油酸酯中制备3-羟基壬酸甲酯的有效方法。应用简单，快速和有效的程序来获得不同的伯和仲，环状和无环酰胺，包括异羟肟酸。在蓖麻油酸和3-羟基壬酸的24种合成衍生物（即甲酯，酰胺和异羟肟酸）中，首次获得并描述了16种化合物。合成的化合物对被测癌细胞具有活性，但对3-羟基壬酸衍生的异羟肟酸具有最佳的细胞毒性作用（11）对抗HeLa细胞。通常，大多数测试化合物对HT29的毒性都比HeLa癌细胞高。结果还表明，特定衍生物的（R）-和（S）-对映体的活性之间没有显着差异。

  DOI：

  10.1007/s00044-019-02348-y

文献信息

• Ozonolytic transformations of olefinic derivatives of L-menthol and ricinolic acid
  作者：G. Yu. Ishmuratov、M. P. Yakovleva、A. Kh. Shayakhmetova、L. P. Botsman、G. V. Nasibullina、R. R. Muslukhov、G. A. Tolstikov

  DOI：10.1007/s10600-006-0240-1

  日期：2006.11

  Ozonolysis and reduction of olefinic derivatives of ricinolic acid and L-menthol were studied using hydroxylamine hydrochloride and sodium trisacetoxyborohydride to reduce the peroxide products.

  研究了蓖麻醇酸和L-薄荷醇的烯烃衍生物的臭氧化和还原反应，使用盐酸羟胺和三乙酰氧基硼氢化钠对过氧化物产物进行了还原。
• Over 98% Optical Yield Achieved by a Heterogeneous Catalysis. Substrate Design and Analysis of Enantio-Differentiating Factors of Tartaric Acid-Modified Raney Nickel Hydrogenation
  作者：Takashi Sugimura、Satoshi Nakagawa、Akira Tai

  DOI：10.1246/bcsj.75.355

  日期：2002.2

  Tartaric acid-modified Raney nickel (TA-MRNi) is a chiral heterogeneous catalyst for the hydrogenation of prochiral ketones. An optical yield (OY) of 86% with methyl acetoacetate (1) as a substrate was improved to 94–96% by employing β-keto esters having a proper bulkiness at the γ -position. The γ -bulkiness effect contributes to a high intrinsic enantio-differentiating ability (factor-i) of the TA-MRNi catalysis. Through the study, we found the best substrate, γ -cyclopropyl-β-keto ester, the hydrogenation of which resulted in 98.6% OY. This further improvement in the OY was ascribed to a smaller contribution of non-enantio-differentiating hydrogenation (N-site catalysis) due to the substrate-specific activation of the enantio-differentiating hydrogenation by the chiral modifier. The OY of the hydrogenation of 1 was analyzed by comparing with well-behaved β-keto esters, and the contribution of the factor-i and the N-site to the OY value was evaluated to deduce the origin of the enantiodifferentiation.

  酒石酸改性的Raney镍(TA-MRNi)是一种手性非均相催化剂，用于前手性酮的氢化反应。以乙酰乙酸甲酯(1)为底物，光学收率(OY)为86%，当采用在γ位置具有适当体积的β-酮酯时，OY提高至94-96%。γ体积效应有助于TA-MRNi催化剂具有高固有的手性区分能力(因子-i)。通过研究，我们发现最佳底物，即γ-环丙基-β-酮酯，其氢化反应的光学收率达到了98.6%。这一光学收率的进一步提升归因于底物特定的手性修饰剂激活手性区分氢化反应，从而减少了非手性区分氢化(N-位点催化)的贡献。通过与表现良好的β-酮酯进行比较，分析了1氢化反应的OY，并评估了因子-i和N-位点对OY值的贡献，从而推导出手性区分的起源。
• Process for producing optically active 3-halogenocarboxylic acid ester and 3-azidocarboxylic acid ester
  申请人：——

  公开号：US20030225301A1

  公开（公告）日：2003-12-04

  A process for producing an optically active 3-azide-carboxylic acid ester by reacting an optically active 3-hydroxycarboxylic acid ester and a thionyl halide in the presence of a basic substance in an organic solvent to produce an optically active 3-halogenocarboxylic acid ester which is then reacted with an azide salt represented by the formula: MN 3 (wherein M is an alkaline metal) in water or a mixture of water and a water soluble organic solvent.

  通过在有机溶剂中，在碱性物质存在下，将光学活性的3-羟基羧酸酯和硫酰卤在一起反应，产生光学活性的3-卤代羧酸酯，然后将其与由公式表示的偶氮盐（其中M是碱性金属）在水或水和水溶性有机溶剂的混合物中反应，从而生产光学活性的3-偶氮基羧酸酯的方法。
• Chemical Synthesis of a Glycolipid Library by a Solid-Phase Strategy Allows Elucidation of the Structural Specificity of Immunostimulation by Rhamnolipids
  作者：Jörg Bauer、Klaus Brandenburg、Ulrich Zähringer、Jörg Rademann

  DOI：10.1002/chem.200600482

  日期：2006.9.18

  variations in the carbohydrate part, the lipid components, and the stereochemistry of the 3-hydroxy fatty acids was designed and synthesized. The enantioselective synthesis of the 3-hydroxy fatty acid building blocks was achieved by employing asymmetric hydrogenation of 3-oxo fatty acids. Glycolipids were prepared by this approach without any intermediary isolation steps, mostly in excellent yields. Final

  描述了通过疏水辅助开关相（HASP）合成的糖脂文库的首次合成。HASP合成可在溶液相步骤和与附着在疏水性二氧化硅载体上的分子进行的固相支持反应之间灵活切换。设计并合成了衍生自先导化合物1-a强免疫刺激鼠李糖脂的糖脂库-碳水化合物部分，脂质成分和3-羟基脂肪酸的立体化学存在差异。通过使用3-氧代脂肪酸的不对称氢化来实现3-羟基脂肪酸结构单元的对映选择性合成。糖脂是通过这种方法制备的，无需任何中间分离步骤，大部分收率都很高。通过酶促酯裂解完成对羧酸的最终脱保护。通过测定细胞因子肿瘤坏死因子α（TNFα）向培养基中的分泌，测试所有制备的鼠李糖脂对人单核细胞的免疫刺激特性。观察到的鼠李糖脂的构效关系表明了一种特定的，基于识别的作用方式，鼠李糖脂的结构变化很小，从而在低微摩尔浓度下对鼠李糖脂的免疫刺激活性产生了强烈影响。
• Synthesis of Rhamnolipid Derivatives Containing Ester Isosteres
  作者：Lei Wang、Todd L. Lowary

  DOI：10.1021/acs.orglett.0c03670

  日期：2020.12.18

  Rhamnolipids are biosurfactants with many applications, arising from their inherent biological activity and their potential as bioremediation agents. Herein, we report the synthesis of four rhamnolipid derivatives in which the ester linkage connecting the two lipid chains in the natural compound is replaced with amide, ketone, ether, or hydrocarbon functional groups. Such compounds are anticipated to

  鼠李糖脂是具有许多应用的生物表面活性剂，这归因于其固有的生物活性和其作为生物修复剂的潜力。本文中，我们报道了四种鼠李糖脂衍生物的合成，其中连接天然化合物中两个脂质链的酯键被酰胺，酮，醚或烃官能团取代。预期此类化合物具有增强的水解稳定性，因此是鼠李糖脂介导的生物学和生物技术的有用探针。