rac-2-庚基硫酸盐 | 103142-08-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 中文名称: rac-2-庚基硫酸盐
• 英文名称: (+/-) Heptan-2-yl-sulfat
• 英文别名: rac-2-heptyl sulfate；Heptan-2-yl hydrogen sulfate
• CAS: 103142-08-1
• 化学式: C₇H₁₆O₄S
• 分子量: 196.268
• InChiKey: IPYWELFAZHBWIY-UHFFFAOYSA-N

物化性质

• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 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：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-2-庚基硫酸盐 在 4-二甲氨基吡啶 、 His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1 、 水 、 三羟甲基氨基甲烷盐酸盐 作用下， 反应 24.0h， 生成 (S)-2-heptyl acetate
  参考文献：
  名称：

  A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols

  摘要：

  A metallo-beta-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec,alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to > 99% ee via a chemoenzymatic deracemization protocol on a preparative scale.

  DOI：

  10.1021/ol201635y
• 作为产物：
  描述：

  2-庚醇 在 三氧化硫-三乙胺复合物 作用下， 以76%的产率得到rac-2-庚基硫酸盐
  参考文献：
  名称：

  A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols

  摘要：

  A metallo-beta-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec,alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to > 99% ee via a chemoenzymatic deracemization protocol on a preparative scale.

  DOI：

  10.1021/ol201635y

文献信息

• Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea
  作者：Sabine R. Wallner、Bettina M. Nestl、Kurt Faber

  DOI：10.1039/b504883d

  日期：——

  rac-sec-Alkyl sulfate esters 1a-8a were resolved in low to excellent enantioselectivities with E-values up to >200 using whole cells of aerobically-grown hyperthermophilic sulfur-metabolizers, such as Sulfolobus solfataricus DSM 1617, Sulfolobus shibatae DSM 5389 and, most notably, Sulfolobus acidocaldarius DSM 639. Significantly enhanced selectivities were obtained using cells grown on sucrose-enriched

  使用需氧生长的嗜热硫代谢物的全细胞，如Sulfolobus solfataricus DSM 1617，Shiulfoloshishibatae DSM 5389，将rac-sec-烷基硫酸酯1a-8a分解为低至优异的对映选择性，E值高达> 200。最值得注意的是，Sulfolobus acidocaldarius DSM639。使用在富含蔗糖的Brock培养基上生长的细胞可以显着提高选择性。已显示该生物水解的立体化学过程在构型的严格颠倒下进行，因此优选的（R）-对映异构体被转化成相应的（S）-仲醇以提供均手性产物混合物。
• Enantioselective Stereoinversion in the Kinetic Resolution of rac-sec-Alkyl Sulfate Esters by Hydrolysis with an Alkylsulfatase from Rhodococcus ruber DSM 44541 Furnishes Homochiral Products
  作者：Mateja Pogorevc、Wolfgang Kroutil、Sabine R. Wallner、Kurt Faber

  DOI：10.1002/1521-3773(20021104)41:21<4052::aid-anie4052>3.0.co;2-w

  日期：2002.11.4