(S)-γ-Hydroxycaproic acid | 97189-67-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-γ-Hydroxycaproic acid
• 英文别名: (4S)-4-hydroxyhexanoic acid
• CAS: 97189-67-8
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: ABIKNKURIGPIRJ-YFKPBYRVSA-N

物化性质

• 沸点：
  280.4±23.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-γ-Hydroxycaproic acid 在 盐酸 作用下， 生成 (S)-4-hexanolide
  参考文献：
  名称：

  Enzymatic resolution of racemic lactones

  摘要：

  DOI：

  10.1016/s0040-4039(00)82077-8
• 作为产物：
  描述：

  4-氧代己酸 在 sodium hydroxide 、 葡萄糖 、 硫酸 作用下， 反应 29.0h， 生成 (S)-γ-Hydroxycaproic acid
  参考文献：
  名称：

  Naoshima, Yoshinobu; Ozawa, Hiroshi; Kondo, Hirokiyo, Agricultural and Biological Chemistry, 1983, vol. 47, # 6, p. 1431 - 1434

  摘要：

  DOI：

文献信息

• Selective Reductions. 59. Effective Intramolecular Asymmetric Reductions of α-, β-, and γ-Keto Acids with Diisopinocampheylborane and Intermolecular Asymmetric Reductions of the Corresponding Esters with <i>B</i>-Chlorodiisopinocampheylborane
  作者：P. Veeraraghavan Ramachandran、Sangeeta Pitre、Herbert C. Brown

  DOI：10.1021/jo025594y

  日期：2002.7.1

  stereochemistry of the products obtained from the intramolecular asymmetric reduction of a series of keto acids with (-)-diisopinocampheylborane and intermolecular asymmetric reduction of the corresponding series of keto esters with (-)-B-chlorodiisopinocampheylborane ((-)-DIP-Chloride) has been made. The stereochemistry of the hydroxy acids from the reduction of keto acids is dependent only on the enantiomer

  分子内不对称还原一系列酮酸用（-）-二异硫代樟脑硼烷和分子间不对称还原相应系列的酮酯与（-）-B-氯二异硫代樟脑硼烷（（-已制成DIP-氯化物。酮酸还原产生的羟基酸的立体化学仅取决于所用试剂的对映异构体。除脂肪族α-酮酯外，由酮酯还原得到的产物的立体化学也是一致的。α-，β-和γ-酮酸在77-98％ee中提供相应的羟基酸，而α-和γ-酮基酯在82->或= 99％ee中提供羟基酯。β-酮酸酯不进行还原。尽管在相同反应条件下不会进行δ-酮酸的还原，但是δ-酮基酯的还原是容易的。将来自γ-酮酸和酯以及δ-酮酯的还原的所有产物转化为相应的内酯。这项研究表明，DIP-氯化物是在低温下还原α-酮酸酯的有效试剂。
• Efficient Intramolecular Asymmetric Reductions of α-, β-, and γ-Keto Acids with Diisopinocampheylborane¹
  作者：P. Veeraraghavan Ramachandran、Herbert C. Brown、Sangeeta Pitre

  DOI：10.1021/ol0062291

  日期：2001.1.1

  [GRAPHICS]alpha-, beta-, and gamma -Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The gamma -hydroxy acids produced were conveniently cyclized to the corresponding lactones, This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.
• BLANCO, B.;GUIBE-JAMPEL, E.;ROUSSEAU, G., TETRAHEDRON LETT., 29,(1988) N 16, 1915-1918
  作者：BLANCO, B.、GUIBE-JAMPEL, E.、ROUSSEAU, G.

  DOI：——

  日期：——
• Method for modifying enzyme and oxidoreductive variant
  申请人：——

  公开号：US20040248250A1

  公开（公告）日：2004-12-09

  An enzyme modifying method for converting the coenzyme-dependency of an oxidoreductase is developed. Using this method, a novel carbonyl reductase mutant capable of utilizing NADH as a coenzyme is provided. It is also intended to provide a process for enzymatically producing an optically active (S)-4-halo-3-hydroxybutyric ester by utilizing the carbonyl reductase mutant. A method for modifying an enzyme itself so as to convert the coenzyme-dependency of a carbonyl reductase which asymmetrically reduces a carbonyl compound to produce an optically active alcohol, a carbonyl reductase having such coenzyme dependency as has been converted from NADPH to NADH which is obtained by the above method, a DNA encoding this enzyme mutant, a plasmid carrying this DNA, a transformant obtained by the transformation with this plasmid, and a process for producing an optically active alcohol by using this enzyme mutant and/or this transformant.
• Process for Production of Optically Active Alcohol
  申请人：Hayashi Motoko

  公开号：US20090203096A1

  公开（公告）日：2009-08-13

  The present invention provides methods for producing (S)-1,1,1-trifluoro-2-propanol, which include the step of reacting an enzyme of any one of alcohol dehydrogenase CpSADH, alcohol dehydrogenase ReSADH, carbonyl reductase ScoPAR, (2S,3S)-butanediol dehydrogenase ZraSBDH, carbonyl reductase ScGCY1, tropinone reductase HnTR1, tropinone reductase DsTR1, or alcohol dehydrogenase BstADHT, a microorganism or a transformant strain that functionally expresses the enzyme, or a processed material thereof, with 1,1,1-trifluoroacetone. The present invention also provides methods for producing (R)-1,1,1-trifluoro-2-propanol, which include the step of reacting alcohol dehydrogenase PfODH, a microorganism or a transformant strain that functionally expresses the enzyme, or a processed material thereof, with 1,1,1-trifluoroacetone.