(R)-2-nonanol

• 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-nonanol
• 英文别名: (R)-nonan-2-ol；(2R)-Nonan-2-OL
• 化学式: C₉H₂₀O
• 分子量: 144.257
• InChiKey: NGDNVOAEIVQRFH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-nonanol 在 甲醇 、 copper(l) iodide 、 trans-[PdClMe(PPh₃)₂] 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 120.0h， 生成
  参考文献：
  名称：

  Lyotropic Chiral Nematic Liquid Crystalline Aliphatic Conjugated Polymers Based on Disubstituted Polyacetylene Derivatives That Exhibit High Dissymmetry Factors in Circularly Polarized Luminescence

  摘要：

  We synthesized disubstituted liquid crystalline polyacetylene (diLCPA) derivatives bearing 4-nonyloxy phenyl groups with lyotropic and thermotropic LC behavior. The poly(diphenylacetylene) main chain structure of the diLCPAs and the chirality induced with either chiral moieties or chiral dopants allow the formation of a highly ordered lyotropic N*-LC phase. Circular dichroism (CD) spectra of the diLCPAs imply that one-handed intrachain helical structures are formed in solution, while interchain helical pi-stacking between the polymer main chains are formed in cast film and in the N*-LC state. Absorption dissymmetry factors (g(abs)) in the N*-LC state show values on the order of 10(-1). The N*-LC state facilitates the formation of helically pi-stacked structures with a high degree of helical ordering of the diLCPA and is indispensable for the generation of circularly polarized luminescence (CPL) with high emission dissymmetry factors (g(em)) on the order of 10(-1). To the best of our knowledge, this is the highest reported value of CPL achieved for aliphatic, conjugated polymers. As an alternative to the thermotropic N*-LC phase, we have found that the lyotropic N*-LC phase of diLCPA could be promising materials possessing CPL functionality for use in next-generation pi-conjugated organic optoelectronic devices, displays, and sensors.

  DOI：

  10.1021/ja3086565
• 作为产物：
  描述：

  2-壬酮 在 NAD-dependent alcohol dehydrogenase 、 phosphate buffer pH 7.0 、 β-烟酰胺腺嘌呤二核苷酸 、 异丙醇 作用下， 生成 (R)-2-nonanol
  参考文献：
  名称：

  具有相反面部选择性的新型NAD依赖性酒精脱氢酶可用于不对称还原和辅因子再生

  摘要：

  从假单胞菌属物种分离出的一种新的NAD依赖性醇脱氢酶催化许多无环酮还原为旋光醇，其对映体选择性非常高（对映体过量90％至> 98％）；还原的立体化学过程被确定为所述的转移亲- （[R ）氢从NADH至硅的羰基，由一个进程不同为其他已知的醇脱氢酶的面。

  DOI：

  10.1039/c39900000677

文献信息

• Identification of key residues in Debaryomyces hansenii carbonyl reductase for highly productive preparation of (S)-aryl halohydrins
  作者：Guo-Chao Xu、Yue-Peng Shang、Hui-Lei Yu、Jian-He Xu

  DOI：10.1039/c5cc06796k

  日期：——

  Key residues were identified through combinatorial mutation of conserved residues with notably improved productivity in asymmetric reduction of α-chloroacetophenone.

  关键残基通过组合突变保守残基而被识别，这种突变显著提高了不对称还原α-氯乙酰苯的产率。
• Identification of an ε-Keto Ester Reductase for the Efficient Synthesis of an (<i>R</i> )-α-Lipoic Acid Precursor
  作者：Yu-Jun Zhang、Wen-Xia Zhang、Gao-Wei Zheng、Jian-He Xu

  DOI：10.1002/adsc.201500001

  日期：2015.5.26

  gave ethyl (R)‐8‐chloro‐6‐hydroxyoctanoate, a key precursor for the synthesis of (R)‐α‐lipoic acid, in high space‐time yield (530 g L−1 d−1) and with excellent enantiomeric excess (>99%). This bioprocess was shown to be viable on a 10‐L scale. This method provides a greener and more cost‐effective method for the industrial production of (R)‐α‐lipoic acid.

  从副产念珠菌中分离出了一种新型的还原酶（Cp AR2），该酶对ε-酮酯（8-氯-6-氧代辛酸乙酯）具有异常高的活性。共表达Cp AR2和葡萄糖脱氢酶基因的大肠杆菌细胞对8-氯-6-氧代辛酸乙酯的不对称还原产生了（R）-8-氯-6-羟基辛酸乙酯，这是合成（R）-α-的关键前体硫辛酸，时空产率高（530 g L -1  d -1），对映体过量极佳（> 99％）。该生物过程显示出在10 L规模上可行。这种方法为工业生产（R）-α-硫辛酸
• Asymmetric reduction of ketones by Geotrichum candidum in the presence of AmberliteTM XAD, a solid organic solvent
  作者：Kaoru Nakamura、Mikio Fujii、Yoshiteru Ida

  DOI：10.1039/b005204n

  日期：——

  A hydrophobic polymer, Amberlite™ XAD, was used as material to control the stereochemical course of microbial reductions. In the presence of XAD, simple aliphatic and aromatic ketones were reduced to the corresponding (S)-alcohols in excellent enantiomeric excess (ee) while low enantioselectivities were observed in the absence of the polymer.

  疏水的 聚合物，Amberlite ™ XAD被用作控制微生物减少的立体化学过程的材料。在XAD存在下，简单的脂肪族和芳香族酮类在极佳的对映体过量（ee）下被还原为相应的（S）醇，而在不存在对映体的情况下观察到低对映选择性聚合物。
• Biocatalytic Asymmetric Hydrogen Transfer Employing <i>Rhodococcus ruber</i> DSM 44541
  作者：Wolfgang Stampfer、Birgit Kosjek、Kurt Faber、Wolfgang Kroutil

  DOI：10.1021/jo026216w

  日期：2003.1.1

  the corresponding ketone using 2-propanol as hydrogen donor or by enantioselective oxidation through kinetic resolution of the rac-alcohol using acetone as hydrogen acceptor employing whole lyophilized cells of Rhodococcus ruber DSM 44541. The microbial oxidation/reduction system exhibits not only excellent stereo- and enantioselectivity but also a broad substrate spectrum. Due to the exceptional tolerance

  具有相对绝对构型的非外消旋仲醇，可通过使用2-丙醇作为氢供体进行不对称还原相应的酮，或通过使用丙酮作为氢受体的外消旋醇的动力学拆分，并利用红球菌DSM的整个冻干细胞，通过对映体选择性氧化获得44541.微生物氧化/还原系统不仅具有出色的立体选择性和对映选择性，而且还具有广泛的底物谱。由于生物催化剂对高浓度的有机材料（溶剂，底物和共底物）具有出色的耐受性，因此该工艺非常高效。生物催化剂的简单制备及其易于处理，使该系统成为用于有机合成的多功能工具。
• Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid
  作者：Jun-ichi Matsuo、Yu Hattori、Mio Hashizume、Hiroyuki Ishibashi

  DOI：10.1016/j.tet.2010.06.012

  日期：2010.8

  Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99%

  通过使用抗-1,3-二醇和催化量的苯中的2,4-二硝基苯磺酸（DNBSA），在回流下将脂肪族酮还原为相应的仲醇。在该介质中加入1-辛硫醇可提高还原效率。通过使用手性抗戊烷-2,4-二醇进行脂族酮的不对称还原，并且在叔烷基酮的还原中观察到高度不对称的诱导作用（最高> 99％ee）。在不存在辛硫醇的情况下，使用手性抗戊烷-2,4-二醇和DNBSA进行的酰基硅烷的不对称还原有效地进行，并以高收率和高ee收率获得了相应的α-甲硅烷基醇。