(S)-2-heptanethiol | 119785-37-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: (S)-2-heptanethiol
• 英文别名: (2S)-heptane-2-thiol
• CAS: 119785-37-4
• 化学式: C₇H₁₆S
• 分子量: 132.27
• InChiKey: DAZNOIJJVKASGS-ZETCQYMHSA-N

物化性质

• 沸点：
  165.4±8.0 °C(Predicted)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-heptanethiol 在 lithium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.6h， 生成 <1S-<1α,2α(Z),3α(R*),4α>>-7-<3-<(2-Heptylthio)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009
• 作为产物：
  描述：

  (R)-(-)-2-庚醇 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-2-heptanethiol
  参考文献：
  名称：

  鉴定和合成2-庚硫醇，这是一种在甜椒中发现的新风味化合物。

  摘要：

  2-庚硫醇首次被鉴定为红色和绿色甜椒提取物的成分。在质谱和保留指数的基础上提出了这种新的香气化合物的化学结构，并通过化学合成和核磁共振光谱测量得到了证实。它的香气特性被描述为含硫，洋葱状和蔬菜状，让人联想到较低浓度的柿子椒，其鼻检测阈值为10微克/升水。对于对映体形式，没有观察到气味说明和阈值的差异，所述对映体形式是通过对甲苯磺酸由对映纯2-庚醇制备，然后进行硫代乙酰化和还原，得到目标硫醇对映体。

  DOI：

  10.1021/jf035008h

文献信息

• 9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists
  作者：Steven E. Hall、Wen Ching Han、Don N. Harris、Anders Hedberg、Martin L. Ogletree

  DOI：10.1021/jm00125a009

  日期：1989.5

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).
• Identification and Synthesis of 2-Heptanethiol, a New Flavor Compound Found in Bell Peppers
  作者：Hervé Simian、Fabien Robert、Imre Blank

  DOI：10.1021/jf035008h

  日期：2004.1.1

  reminiscent of bell pepper at lower concentrations, with an orthonasal detection threshold of 10 microg/L of water. No differences in odor note and threshold value were observed for the enantiomeric forms, which were prepared from enantiopure 2-heptanol by tosylation, followed by thioacetylation and reduction, giving the target thiol enantiomers.

  2-庚硫醇首次被鉴定为红色和绿色甜椒提取物的成分。在质谱和保留指数的基础上提出了这种新的香气化合物的化学结构，并通过化学合成和核磁共振光谱测量得到了证实。它的香气特性被描述为含硫，洋葱状和蔬菜状，让人联想到较低浓度的柿子椒，其鼻检测阈值为10微克/升水。对于对映体形式，没有观察到气味说明和阈值的差异，所述对映体形式是通过对甲苯磺酸由对映纯2-庚醇制备，然后进行硫代乙酰化和还原，得到目标硫醇对映体。