(S)-5-chloro-2-pentanol | 99212-19-8

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-chloro-2-pentanol
• 英文别名: (S)-(+)-5-chloropentan-2-ol；(S)-5-Chloropentan-2-ol；(2S)-5-chloropentan-2-ol
• CAS: 99212-19-8
• 化学式: C₅H₁₁ClO
• 分子量: 122.595
• InChiKey: FLSMMDCDBMBKCE-YFKPBYRVSA-N

物化性质

• 沸点：
  174.5±23.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  3
• 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：

  (S)-5-chloro-2-pentanol 在 对甲苯磺酸 、 magnesium 、 1,2-二溴乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 20.33h， 生成 (7S)-(+)-3-hydroxy-1-phenyl-7-(tetrahydropyranyl-2-oxy)oct-1-ene
  参考文献：
  名称：

  Organic synthesis with enzymes. 3. TBADH-catalyzed reduction of chloro ketones. Total synthesis of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid: a civet constituent

  摘要：

  DOI：

  10.1021/ja00272a051
• 作为产物：
  描述：

  (+)-(S)-4-(benzyloxy)pentan-1-ol 在 palladium on activated charcoal 草酰氯 、 氢气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-5-chloro-2-pentanol
  参考文献：
  名称：

  Enantioconvergent Formal Synthesis of Brefeldin A via Sakai-Catalyzed Cyclization

  摘要：

  DOI：

  10.1021/jo990507w

文献信息

• Asymmetric Reduction of Ketones by the Acetone Powder of <i>Geotrichum </i><i>c</i><i>andidum</i>
  作者：K. Nakamura、T. Matsuda

  DOI：10.1021/jo9812779

  日期：1998.11.1

  Aromatic ketones, beta-keto esters, and simple aliphatic ketones were reduced with excellent selectivity to the corresponding (S)-alcohols by using the acetone powder of Geotrichum candidum. This method is superior in reactivity and stereoselectivity to reduction by the whole-cell. The experimental conditions for the reduction system such as ratio of the biocatalyst to the substrate, kinds of coenzymes, alcohol for coenzyme regeneration, and buffer, pH, and reaction temperature were investigated, and stability and preservability of the biocatalyst were also examined. This method is very convenient for the synthesis of optically pure alcohols on a gram scale.
• Thermostable enzymes in organic synthesis. 2. Asymmetric reduction of ketones with alcohol dehydrogenase from Thermoanaerobium brockii
  作者：Ehud. Keinan、Eva K. Hafeli、Kamal K. Seth、Raphael. Lamed

  DOI：10.1021/ja00261a026

  日期：1986.1
• Practical Application of Recombinant Whole-Cell Biocatalysts for the Manufacturing of Pharmaceutical Intermediates Such as Chiral Alcohols
  作者：Akinobu Matsuyama、Hiroaki Yamamoto、Yoshinori Kobayashi

  DOI：10.1021/op025514s

  日期：2002.7.1

  We have developed efficient biocatalytic processes for the preparation of chiral alcohols, such as (R)-1,3-butanediol, ethyl (S)-4-chloro-3-hyroxybutanoate, ethyl (R)-4-chloro-3-hyroxybutanoate, (S)-5-chloro-2-pentanol, (R)-5-chloro-2-pentanol, and (S)-cyclopropylethanol by stereospecific enzymatic oxidoreduction on a practical level. These chiral alcohols are very important synthons for the synthesis of various pharmaceutical intermediates that lead to antibiotics and inhibitors of HMG-CoA reductase. Here, we present practical applications on biocatalysis using novel recombinant whole-cell biocatalysts that catalyzed enantioselective oxidation and asymmetric reduction with a coenzyme regeneration system.
• A Pseudomonas sp. alcohol dehydrogenase with broad substrate specificity and unusual stereospecificity for organic synthesis
  作者：Curt W. Bradshaw、Hong Fu、Gwo Jenn Shen、Chi Huey Wong

  DOI：10.1021/jo00031a036

  日期：1992.2

  A new alcohol dehydrogenase from Pseudomonas sp. strain PED has been isolated and characterized. The enzyme exhibits a broad substrate specificity, accepting aromatic, cyclic, and aliphatic compounds as substrates. The K(m) values were determined as 525-mu-M for NAD and 75-mu-M for 2-propanol with a specific activity of 36 U/mg. The kinetic mechanism is ordered bi-bi with the cofactor binding first and releasing last. The enzyme transfers the pro-R hydride of NADH to the si face of carbonyl compounds to yield (R) alcohols. Synthetic-scale reductions of a number of representative compounds were carried out in high enantiomeric excess with in situ regeneration of NADH using 2-propanol as the hydride source and the same enzyme as catalyst.
• KEINAN, EHUD, RAPP./INGENJORSVETENSKAPSAKAD,(1988) N46, C. 6-8
  作者：KEINAN, EHUD

  DOI：——

  日期：——