ethyl (-)-(3R)-3-hydroxyoctanoate | 118918-31-3

• 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: ethyl (-)-(3R)-3-hydroxyoctanoate
• 英文别名: ethyl (3R)-3-hydroxyoctanoate；ethyl (R)-3-Hydroxyoctanoate；ethyl 3-hydroxyoctanoate；r-Ethyl-3-hydroxyoctanoate
• CAS: 118918-31-3
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: VGWUJHSTGYCXQQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：

  ethyl (-)-(3R)-3-hydroxyoctanoate 在 sodium hydroxide 作用下， 以100%的产率得到(R)-3-hydroxyoctanoic acid
  参考文献：
  名称：

  Coupling of alkynyl organometallics with 4-acetoxy-1,3-dioxanes: Synthesis of propargylic and allylic anti-1,3-diols

  摘要：

  Alkynyl diethylalanes and stannanes couple with 4-acetoxy-1,3-dioxane 1 in the presence of BF3 . OEt2 to give acetal protected propargylic anti-1,3-diols 2 in high yield, with exquisite diastereoselectivity and little acetal epimerization. These propargylic dioxanes 2 are useful intermediates for further diastereoselective reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00512-7
• 作为产物：
  描述：

  3-氧代辛酸乙酯 在 氢气 作用下， 以 甲醇 为溶剂， 生成 ethyl (-)-(3R)-3-hydroxyoctanoate
  参考文献：
  名称：

  Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase

  摘要：

  Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report oil the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and arnino ester substitutions were altered and tile resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display all increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings Support the idea that all orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.

  DOI：

  10.1021/jm800321h

文献信息

• A Chiral 6-Membered <i>N</i>-Heterocyclic Carbene Copper(I) Complex That Induces High Stereoselectivity
  作者：Jin Kyoon Park、Hershel H. Lackey、Matthew D. Rexford、Kirill Kovnir、Michael Shatruk、D. Tyler McQuade

  DOI：10.1021/ol1021756

  日期：2010.11.5

  A chiral 6-membered annulated N-heterocyclic (6-NHC) copper complex that catalyzes β-borylations with high yield and enantioselectivity was developed. The chiral 6-NHC copper complex is easy to prepare on the gram scale and is very active, showing 10 000 turnovers at 0.01 mol % of catalyst without significant decrease of enantioselectivity and with useful reaction rates.

  开发了一种手性的六元环状N-杂环（6-NHC）铜络合物，它以高收率和对映选择性催化β-硼化。手性6-NHC铜络合物易于按克规模制备，并且非常活泼，在0.01 mol％的催化剂下显示出1万的周转率，而对映选择性没有显着降低，并且具有有用的反应速率。
• Kinetic resolution of aliphatic acyclic β-hydroxyketones by recombinant whole-cell Baeyer–Villiger monooxygenases—Formation of enantiocomplementary regioisomeric esters
  作者：Jessica Rehdorf、Alenka Lengar、Uwe T. Bornscheuer、Marko D. Mihovilovic

  DOI：10.1016/j.bmcl.2009.05.014

  日期：2009.7

  substrates in the enzymatic kinetic and regioselective Baeyer–Villiger oxidation catalyzed by 12 Baeyer–Villiger monooxygenases from different bacterial origin. Excellent enantioselectivities (E >100) could be observed with 4-hydroxy-2-ketones. After acyl migration, the ester undergoes hydrolysis followed by the formation of optically active 1,2-diols. Furthermore, resolution of 5-hydroxy-3-ketones gave

  研究了一组不同的线性脂族β-羟基酮作为底物，这些底物是由12种不同细菌来源的Baeyer-Villiger单加氧酶催化的酶动力学和区域选择性Baeyer-Villiger氧化作用的。用4-羟基-2-酮可以观察到极好的对映选择性（E > 100）。酰基迁移后，酯进行水解，然后形成光学活性的1,2-二醇。此外，通过5-羟基-3-酮的拆分，可以得到“异常”酯，从而扩大了这些酶在有机化学中的适用性。另外，注意到，几种底物被不同的酶以对映体互补的方式并具有高光学纯度被转化。
• Enantioselective Entry to theHomalium Alkaloid Hoprominol: Synthesis of an (R,R,R)-Hoprominol Derivative
  作者：Corinne Ensch、Manfred Hesse

  DOI：10.1002/hlca.200390016

  日期：2003.1

  the chiral β-amino acid portions 10a and 10b, respectively, by application of a set of reactions (e.g., N-alkylation of 10a,b and Sb(OEt)3-assisted cyclization of the resulting open-chain intermediates) already known. In comparison with the total syntheses of homaline (1) and homoprine (2), the newness of the described synthesis lies in the asymmetric approach to the difunctionalized fatty acid derivative

  描述了N-和O-保护的hoprominol衍生物（R，R，R）-6的非对映选择性合成。通过环化制备两个基本手性氮杂内酰胺单元7a和7b并随后通过已知方法进行它们的迭代连接，成功构建了双环O-甲硅烷基化和二（N-甲苯磺酰基化）不对称支架6（方案5）。由手性β制备4-烷基-六氢-1，5-重氮星-2（1 H）-酮7a和7b。α-氨基酸部分10A和10B分别，由一组反应（应用例如，N的烷基化10A，b和Sb（OET）3已经知道所得到的开链中间体的环化-assisted）。与homaline（1）和homoprine（2）的总合成相比，所述合成的新颖之处在于从（-）-（S）-苹果酸（9）开始的双官能化脂肪酸衍生物10b的不对称方法。（方案3和4）。制备10b的关键步骤是光学纯的非对映胺化α，β不饱和δ -羟基高烯丙基酯14经由共轭分子内氮杂迈克尔非环的环化δ - （氨基甲酰氧基）中间体11。
• Triptycene-Based Chiral and<i>meso</i>-N-Heterocyclic Carbene Ligands and Metal Complexes
  作者：Roman Savka、Marvin Bergmann、Yuki Kanai、Sabine Foro、Herbert Plenio

  DOI：10.1002/chem.201601474

  日期：2016.7.4

  metal complexes [(NHC)MX] (M=Cu, Ag, Au; X=Cl, Br) and [(NHC)MCl(cod)] (M=Rh, Ir; cod=1,5‐cyclooctadiene) in good yields. The new azolium salts and metal complexes suffer from limited solubility in common organic solvents. Consequently, the introduction of solubilizing groups (such as 2‐ethylhexyl or 1‐hexyl by O‐alkylation) is essential to render the complexes soluble. The triptycene unit infers special

  基于1-氨基-4-羟基三茂碳烯，从乙二醛衍生的二亚胺合成了新的饱和和不饱和的三茂碳NHC（N杂环卡宾）配体。将各自的羧化物转化为金属络合物[（NHC）MX]（M = Cu，Ag，Au; X = Cl，Br）和[（NHC）MCl（cod）]（M = Rh，Ir; cod = 1， 5-环辛二烯）的收率很高。新的偶氮盐和金属络合物在普通有机溶剂中的溶解度有限。因此，引入增溶基团（例如通过O-烷基化作用的2-乙基己基或1-己基）对于使复合物可溶至关重要。三并茂单元可对金属络合物产生特殊的空间位阻特性，从而可以对靠近金属中心的选定区域进行空间位阻。接下来，手性和介观制备了基于三茂基的N杂环卡宾配体。合成手性配体的关键步骤是用（1 S，2 S）-1,2-二苯基-1,2-二氨基乙烷将1-溴-4-丁氧基三茂烯进行布赫瓦尔德-哈特维格胺的胺化反应，然后环化与HC（OEt）3形成的唑啉鎓盐。与内消旋-1,2-二苯基-1
• Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds
  作者：Gary A. Molander、Steven R. Wisniewski、Mona Hosseini-Sarvari

  DOI：10.1002/adsc.201300640

  日期：2013.10.11

  Enantioenriched potassium beta-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)diboron to alpha,beta-unsaturated amides. These dibora reagents provide access to the desired organotrifluoroborates using effective and atom economical sources of boron. The copper-catalyzed beta-boration is extended to

  Enantioenriched 钾β-trifluoroboratoamides 已通过不对称、 铜催化1,4-加成四羟基二硼(BBA) 和四(二甲氨基) 二硼合成α，β-不饱和酰胺。这些二硼试剂使用有效且原子经济的硼源提供了获得所需有机三氟硼酸盐的途径。铜催化的 β-硼酸化扩展到 α,β-不饱和酮和酯。合成的有机三氟硼酸钾的产率高达 92%，对映体比例高达 98:2。当金属转移通过 SE2 机制通过开放过渡态进行时，富含对映体的 β-三氟硼酰胺钾与一系列芳基和杂芳基氯化物成功交叉偶联，具有完全立体化学保真度。