1-(2-methyl-1,3-dithian-2-yl)cyclopentan-1-ol | 936231-48-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 1-(2-methyl-1,3-dithian-2-yl)cyclopentan-1-ol
• CAS: 936231-48-0
• 化学式: C₁₀H₁₈OS₂
• 分子量: 218.384
• InChiKey: SXYNQIANYBKTIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-1,3-dithian-2-yl)cyclopentan-1-ol 在 甲醇 、 lithium hydroxide 、 mercury(II) perchlorate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Spirocyclopentyl-4,5-dihydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x
• 作为产物：
  描述：

  2-甲基-1,3-二噻烷 、 环戊酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-(2-methyl-1,3-dithian-2-yl)cyclopentan-1-ol
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x

文献信息

• Photocatalytic Reductive Radical‐Polar Crossover for a Base‐Free Corey–Seebach Reaction
  作者：Karsten Donabauer、Kathiravan Murugesan、Urša Rozman、Stefano Crespi、Burkhard König

  DOI：10.1002/chem.202003000

  日期：2020.10.9

  abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α‐hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated

  在有机合成中，无金属的碳负离子亲核体的产生至关重要。本文中，我们报告了一种对Corey–Seebach反应的光催化方法。提出的方法在温和的氧化还原中性和无碱条件下运行，从而提供具有高官能团耐受性的所需产品。通过光和氢原子转移（HAT）催化的组合可以实现反应。这种催化合并使CH可以通过夺取氢原子然后进行自由基还原来进行碳负离子活化。然后，所产生的亲核中间体能够加成至羰基亲电子体。在随后的步骤中，可以很容易地将获得的二噻吩转化为有价值的α-羟基羰基。所提出的反应机理得到了发射猝灭的支持，