rac-1-heptyn-3-yl sulfate | 1316793-69-7

• 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
• 英文名称: rac-1-heptyn-3-yl sulfate
• CAS: 1316793-69-7
• 化学式: C₇H₁₂O₄S
• 分子量: 192.236
• InChiKey: GDWBIXIUYYDATD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  rac-1-heptyn-3-yl sulfate 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 (R)-1-heptyn-3-yl 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：

  1-庚炔-3-醇 在 三氧化硫-三乙胺复合物 作用下， 以82%的产率得到rac-1-heptyn-3-yl sulfate
  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

• A Stereoselective Inverting <i>sec</i>-Alkylsulfatase for the Deracemization of <i>sec</i>-Alcohols
  作者：Markus Schober、Petra Gadler、Tanja Knaus、Heidemarie Kayer、Ruth Birner-Grünberger、Christian Gülly、Peter Macheroux、Ulrike Wagner、Kurt Faber

  DOI：10.1021/ol201635y

  日期：2011.8.19

  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.