(R)-3-methyl-2-nonanone | 20659-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-methyl-2-nonanone
• 英文别名: (R)-3-methylnonan-2-one；(3R)-3-methylnonan-2-one
• CAS: 20659-77-2
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: BMLJPODSPMQJKF-SECBINFHSA-N

物化性质

• 沸点：
  199.3±8.0 °C(Predicted)
• 密度：
  0.817±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-壬酮 在 吗啉 、 baker's yeast Saccharomyces cerevisiae 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 120.0h， 生成 (R)-3-methyl-2-nonanone
  参考文献：
  名称：

  Baker's yeast reduction of α-methyleneketones

  摘要：

  The bioreduction of alpha -methyleneketones. (RC)-C-1(-O)C(-CH2)R-2 (R-1= Me, Et, Pr, iso-Bu, Ph. CH2CH2Ph: R-2 =Cl, Me, Et, n-Pr, iso-Pr. n-Bu, n-C6H13, Ph, CH2Ph), was mediated by baker's yeast (Saccharomyees cerevisiae) to obtain the corresponding alpha -methylkelones. The R-1 and R-2 groups had a significant influence on the rate and enantioselectivity of the reductions. The rate or C-C bond reduction was higher than that of C-O bond reduction. Only alpha -methyleneketones having R-1 = Me yielded alpha -methylketones in high enantioselectivity with e.e.s of 88-99%. (C) 2001 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00134-3

文献信息

• Bioreduction of α-Acetoxymethyl Enones: Proposal for an S_N2′ Mechanism Catalyzed by Enereductase
  作者：Bruno R. S. Paula、Davila Zampieri、J. Augusto R. Rodrigues、Paulo J. S. Moran

  DOI：10.1002/adsc.201600601

  日期：2016.11.17

  acylated Morita–Baylis–Hillman adduct 1‐acetoxy‐2‐methylene‐1‐phenylbutan‐3‐one produced a mixture of products, with and without the acetoxy group, via three different reaction pathways. In addition to experiments employing whole cells, those in which isolated enereductases were used suggested that the main pathway through which the loss of the acetoxy group occurs during the biocatalytic cascade is an SN2′‐type

  （Z）-3-乙酰氧基甲基-4-R-3-丁烯-2-酮（R =芳基，烷基）和（Z）-3-甲基-4-R-3-丁烯-2-丁烯（R =芳基）合成并通过酿酒酵母进行还原，分别产生（R）-和（S）-4-R-3甲基丁烷-2-。这种立体化学控制策略适用于对映体过量至中度过量的（R）-和（S）-Tropional®的合成。其他（Z）-3-酰氧基甲基-4-苯基-3-丁烯-2-酮的行为与（Z）-3-乙酰氧基甲基对应物和酰化的Morita-Baylis-Hillman加合物1-乙酰氧基-2-亚甲基-1-苯基丁烷-3-酮通过三种不同的反应途径生成了带有或不带有乙酰氧基的产物混合物。除了使用全细胞的实验外，使用分离的烯还原酶的实验还表明，在生物催化级联反应中发生乙酰氧基丢失的主要途径是S N 2'型反应，而不是正式的氢加成反应。消除乙酸。最后，相关的乙基烯酮被酵母白色念珠菌对映体选择性还原，产生（R）-和（S）还原产物，取决于起始原料中乙酰氧基的存在。
• Asymmetric Reduction of Carbon–Carbon Double Bonds of Conjugated Enones with Fermenting Bakers’ Yeast
  作者：Takashi Sakai、Syuji Matsumoto、Syukou Hidaka、Norihisa Imajo、Sadao Tsuboi、Masanori Utaka

  DOI：10.1246/bcsj.64.3473

  日期：1991.11

  Bakers’ yeast reduction of α-substituted or β,β-disubstituted α,β-unsaturated ketones gave saturated chiral ketones with excellent optical purity, while the β,β-disubstituted derivative remained intact.

  面包师酵母对 α-取代或 β,β-二取代 α,β-不饱和酮的还原得到具有优异光学纯度的饱和手性酮，而 β,β-二取代衍生物保持完整。
• Enantiopure Acetals of α-Alkynyl Carbonyl Compounds: Organoaluminum-Mediated 1,2-Shift of Cobalt-Complexed Alkynyl Group with Concomitant Capture by a Nucleophile
  作者：Kimiko Taya、Tetsuya Nagasawa、Keisuke Suzuki

  DOI：10.1055/s-1997-776

  日期：1997.3

  Upon treatment with the organoaluminum-based combination of Lewis acid and nucleophile, chiral mesyloxy acetal having a Co-complexed alkynyl group undergoes stereospecific 1,2-shift of the complexed alkynyl and the concomitant attack of te ligand R of the organoaluminum reagent. Decomplexation of the products with CAN gives the chiral acetals of α-alkynyl carbonyl compounds in enantiomerically pure form in high yields.

  在用路易斯酸和亲核试剂的基于有机铝的组合处理后，具有共络合炔基的手性甲磺酰氧基缩醛经历络合炔基的立体特异性1，2-位移以及有机铝试剂的配体R的伴随攻击。用 CAN 对产物进行解络，以高产率得到对映体纯形式的 α-炔基羰基化合物的手性缩醛。
• Process for production of lipstatin and microorganisms therefore
  申请人：KRKA, D.D., Novo Mesto

  公开号：EP2141236A1

  公开（公告）日：2010-01-06

  This invention relates to improved processes for the production of lipstatin and /or orlistat and means therefore. In particular, the invention relates to microorganisms characterized by abolished or reduced activity of the BKD complex, e.g. mutated branched-chain 2-oxo acid dehydrogenase (BKD) having reduced or abolished activity, nucleotide sequences suitable for achieving reduced or abolished BKD activity, and microorganisms having reduced or abolished BKD activity. The invention in particular relates to lipstatin-producing microorganisms of the genus Streptomyces. Furthermore, this invention relates to the use of these nucleotide sequences, microorganisms or BKD having reduced or abolished activity in the production of lipstatin and/or orlistat.

  本发明涉及脂肪司他汀和/或奥利司他的改进生产工艺及其方法。特别是，本发明涉及以 BKD 复合物活性减弱或丧失为特征的微生物，例如，活性减弱或丧失的突变支链 2-氧代酸脱氢酶（BKD）、适用于实现 BKD 活性减弱或丧失的核苷酸序列以及 BKD 活性减弱或丧失的微生物。本发明尤其涉及链霉菌属的产脂素微生物。此外，本发明还涉及在生产脂司他丁和/或奥利司他中使用这些核苷酸序列、微生物或活性降低或消失的BKD。
• Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
  作者：Bruno R.S. de Paula、Dávila S. Zampieri、J. Augusto R. Rodrigues、Paulo J.S. Moran

  DOI：10.1016/j.tetasy.2013.07.007

  日期：2013.9

  Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten-2-one (R = n-pentyl, phenyl, 2'- and 4'-chlorophenyl, 3'- and 4'-nitrophenyl, 4'-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae and Geotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.