methyl (R)-2-hydroxydodecanoate | 76835-66-0

• 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)-2-hydroxydodecanoate
• 英文别名: (R)-methyl 3-hydroxydodecanoate；(R)-β-hydroxydodecanoic acid methyl ester；methyl (3R)-3-hydroxydodecanoate；(R)-hydroxydodecyl acid methyl ester；D(-)-3-Hydroxy-laurinsaeure-methylester；methyl (R)-3-hydroxydodecanoate
• CAS: 76835-66-0
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: OZXCINYANGIBDB-GFCCVEGCSA-N

物化性质

• 熔点：
  28-29 °C
• 沸点：
  327.7±15.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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)-2-hydroxydodecanoate 在 zinc p-tert-butylbenzoate lithium hydroxide 、 2-甲基-2-丁烯 、 4 A molecular sieve 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 (3R)-3-[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxydodecanoic acid
  参考文献：
  名称：

  Total synthesis of arthrobacilin A

  摘要：

  Novel cyclic glycolipids, arthrobacilin A and its analogues, have been synthesized by means of unique DCC/DMAP.HCl promoted oligomerization/cyclization, zinc salt catalyzed beta-selective glycosylation, and Noyori's BINAP/Ru catalyzed asymmetric reduction.

  DOI：

  10.1016/s0040-4039(00)76898-5
• 作为产物：
  描述：

  3-oxo-dodecanoic acid 在 potassium dihydrogenphosphate 、 baker's yeast 、 葡萄糖 作用下， 以 乙醚 、 水 为溶剂， 反应 12.0h， 生成 methyl (R)-2-hydroxydodecanoate
  参考文献：
  名称：

  Asymmetric reduction of aliphatic short- to long-chain .beta.-keto acids by use of fermenting bakers' yeast

  摘要：

  DOI：

  10.1021/jo00299a041

文献信息

• Asymmetric Synthesis of Sphinganine and Clavaminol H
  作者：Ramzi Ait-Youcef、Xavier Moreau、Christine Greck

  DOI：10.1021/jo1003899

  日期：2010.8.6

  An efficient enantioselective synthesis of sphinganine and clavaminol H is reported. These sphingoid-type bases were obtained from commercially available fatty acids using highly enantioselective Ru-catalyzed hydrogenation and organocatalytic electrophilic amination reactions to create the stereogenic centers.

  报道了一种有效的对映体选择性合成斯潘加宁和卡瓦米酚H的方法。这些鞘氨醇型碱是通过使用高度对映选择性的Ru催化的氢化反应和有机催化的亲电胺化反应从立体异构中心获得的，可从市售脂肪酸中获得。
• Asymmetric synthesis of long chain β-hydroxy fatty acid methyl esters as new elastase inhibitors
  作者：Belma Hasdemir、Hülya Çelik Onar、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2012.07.004

  日期：2012.7

  methyl esters with an even carbon chain length of 12–20 1b–5b were synthesized by three different asymmetric reduction methods I, II III from their corresponding β-keto methyl esters 1a–5a with the aim of determining their elastase activities. In method I, chiral catalyst A was prepared from chiral ligand (R)-binaphthol 1, while in method II, chiral catalyst B was synthesized from (2R,3R)-diisopropyl tartrate

  本文中，通过三种不同的不对称还原方法I，II III，由相应的β-酮甲基酯1a - 5a合成了碳链长度为12-20 1b - 5b的β-羟基甲基酯，以测定其弹性蛋白酶。活动。在方法I，手性催化剂甲从手性配体（其制备- [R ）-联萘酚1，而在方法II中，手性催化剂乙从（2合成[R，3 - [R ）-二异丙酒石酸2。手性催化剂B以前未曾用于硼烷的不对称还原或手性β-羟基甲基酯的不对称合成中。在方法III中，通过（R）-Me-CBS恶唑硼烷3催化不对称还原。在所有这些方法中，氢化物转移都是通过BH 3 ·SMe 2进行的。用方法I和（R）合成具有（S）构型的手性羟甲基酯。）-通过方法II和III进行配置。通过手性HPLC分析获得的手性羟基甲基酯的ee％值。方法I，II和III首次应用于长链β-酮甲基酯。根据反应的收率和对映体过量，根据碳链长度和手性催化剂与β-酮甲基酯的可变比例，对还原方法I，
• Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
  作者：Andrew Giltrap、Katie Cergol、Angel Pang、Warwick Britton、Richard Payne

  DOI：10.3390/md11072382

  日期：——

  The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative

  报告了海洋衍生的脂肽天然产物 flutamide B 和脱氧 fellutamides B、C 和 D 的全合成。这些化合物是通过使用 Weinreb 酰胺衍生树脂的新型固相合成策略获得的。作为合成的一部分，利用布朗烯丙基化反应和氧化裂解-氧化序列作为关键步骤开发了一种新的 (3R)-羟基月桂酸的对映选择性路线。这些天然产物和天然产物类似物的活性也在体外针对结核分枝杆菌进行了评估。
• 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。
• The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII.
  作者：Masaaki Nakahata、Motomasa Imaida、Hiroshi Ozaki、Tadao Harada、Akira Tai

  DOI：10.1246/bcsj.55.2186

  日期：1982.7

  acid–NaBr–modified Raney nickel catalyst ((R,R)-TA–NaBr–MRNi) gave methyl (R)-3-hydroxyalkanoate (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12) in an average optical yield of 85%. After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (R)-3-hydroxyalkanoic acid (CH

  3-氧代链烷酸甲酯 (CH3(CH2)nCOCH2COOCH3, n=0, 6, 8, 10, 12) 在 (R,R)-酒石酸-NaBr-改性阮内镍催化剂（(R, R)-TA-NaBr-MRNi) 生成 (R)-3-羟基链烷酸甲酯 (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12)，平均光学产率为 85%。在甲酯转化为 3-羟基链烷酸的二环己基铵盐后，该盐从乙腈中重结晶 3 次，然后用酸处理得到光学纯的 (R)-3-羟基链烷酸 (CH3(CH2)nCH(OH) CH2COOH，n=0, 6, 8, 10, 12) 以合理的产率。从与 (S,S)-TA-NaBr-MRNi 的氢化产物中，通过与上述相同的方法获得光学纯的 (S)-3-羟基链烷酸。