(R)-5-氯-2-戊醇 | 76188-95-9

• 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
• 中文名称: (R)-5-氯-2-戊醇
• 英文名称: (R)-5-Chloro-2-pentanol
• 英文别名: (2R)-5-chloropentan-2-ol
• CAS: 76188-95-9
• 化学式: C₅H₁₁ClO
• 分子量: 122.595
• InChiKey: FLSMMDCDBMBKCE-RXMQYKEDSA-N

物化性质

• 沸点：
  174.5±23.0 °C(Predicted)
• 密度：
  1.094 g/mL at 20 °C(lit.)

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

安全信息

• 安全说明：
  S23,S24/25
• 危险类别码：
  R10
• 海关编码：
  2905590090
• 危险品运输编号：
  UN 1987 3/PG 3

反应信息

• 作为产物：
  描述：

  5-氯-2-戊酮 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)-5-氯-2-戊醇
  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

• A new NAD-dependent alcohol dehydrogenase with opposite facial selectivity useful for asymmetric reduction and cofactor regeneration
  作者：Gwo-Jenn Shen、Yi-Fong Wang、Curt Bradshaw、Chi-Huey Wong

  DOI：10.1039/c39900000677

  日期：——

  A new NAD-dependent alcohol dehydrogenase isolated from a Pseudomonas species catalysed the reduction of many acyclic ketones to optically active alcohols with very high enantioselectivity (90 to >98% enantiomeric excess); the stereochemical course of the reduction was determined to be the transfer of the pro-(R) hydrogen from NADH to the Si face of the carbonyl group, a process different from that

  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。
• 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.
• Lactobacillus kefir alcohol dehydrogenase: a useful catalyst for synthesis
  作者：Curt W. Bradshaw、Werner Hummel、Chi Huey Wong

  DOI：10.1021/jo00031a037

  日期：1992.2

  The alcohol dehydrogenase from Lactobacillus kefir simultaneously catalyzes carbonyl reductions and NADPH regeneration in the presence of 2-propanol. Representative synthesis of a number of chiral alcohols was accomplished in good yield and high enantiomeric excess (94-99%). This NADPH-requiring enzyme transfers the pro-R hydride from the cofactor to the si face of carbonyls to give (R) alcohols. The enzyme exhibits a very broad substrate specificity and high enantioselectivity for the synthesis of chiral aromatic, cyclic, polycyclic, and aliphatic alcohols.
• US5225339A
  申请人：——

  公开号：US5225339A

  公开（公告）日：1993-07-06
• US5342767A
  申请人：——

  公开号：US5342767A

  公开（公告）日：1994-08-30