cis-1,2-dimethoxycyclopentane | 61011-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1,2-dimethoxycyclopentane
• 英文别名: cis-Dimethoxycyclopentan；(1S,2R)-1,2-dimethoxycyclopentane
• CAS: 61011-51-6
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: YLBQPTZQSYROOF-KNVOCYPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ((1S,2S)-2-Methoxy-cyclopentylselanyl)-benzene 在 Oxone 、 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 cis-1,2-dimethoxycyclopentane
  参考文献：
  名称：

  Oxone Oxidation of Selenides: A Mild and Efficient Method for the Preparation of Selenones

  摘要：

  DOI：

  10.1021/jo00131a018

文献信息

• Selective radical-chain epimerisation at electron-rich chiral tertiary C–H centres using thiols as protic polarity-reversal catalysts
  作者：Hai-Shan Dang、Brian P. Roberts、Derek A. Tocher†

  DOI：10.1039/b103558b

  日期：——

  Radical-chain epimerisation at chiral tertiary CH centres adjacent to ethereal oxygen atoms can be brought about in the presence of thiols, the function of which is to act as protic polarity-reversal catalysts for hydrogen-atom transfer between pairs of nucleophilic α-alkoxyalkyl radicals. The viability of the method is demonstrated by epimerisation of a series of simple molecules that contain two chiral centres and then the procedure is applied to more complex carbohydrate-based systems, where it is possible to convert a readily available diastereoisomer into a rarer one in a straightforward manner. Of necessity, epimerisation always proceeds in the direction of thermodynamic equilibrium and, in general, the results obtained are in accord with the predictions of molecular mechanics calculations using the MMX force-field. When the required isomer is less stable than the starting diastereoisomer, thiol-catalysed epimerisation of a suitable derivative of the parent can provide a means to obtain the desired compound in satisfactory yield, after deprotection of the epimerised derivative. This strategy is demonstrated for the conversion of trans-cyclohexane-1,2-diol into the less stable cis-isomer and for related contra-thermodynamic isomerisation of some carbohydrates, as well as for the conversion of meso-1,2-diphenylethane-1,2-diol into the dl-form. Thiol-catalysed epimerisation at a CH centre adjacent to an ether-oxygen atom is much faster than at a similar centre adjacent to an amido-nitrogen atom, a result that can be understood in terms of the importance of polar effects on the rate of abstraction of hydrogen by electrophilic thiyl radicals.

  硫醇的作用是作为亲核δ-烷氧基烷基自由基对之间氢原子转移的原生极性反转催化剂，可以在邻近乙氧基原子的手性三级 CH 中心实现自由基链表并化。通过对一系列含有两个手性中心的简单分子进行外延二聚化，证明了该方法的可行性，然后将该程序应用于更复杂的基于碳水化合物的体系，在这些体系中，可以通过直接的方式将容易获得的非对映异构体转化为较罕见的非对映异构体。必要时，二聚化总是朝着热力学平衡的方向进行，一般来说，所获得的结果与使用 MMX 力场进行分子力学计算的预测结果一致。当所需异构体的稳定性低于起始非对映异构体时，可采用巯基催化母体的适当衍生物进行外延化反应，在对外延化衍生物进行脱保护处理后，以令人满意的收率获得所需化合物。这种策略在反式-1,2-环己烷二醇转化为稳定性较差的顺式异构体、某些碳水化合物的相关逆热力学异构化以及介-1,2-二苯基乙烷-1,2-二醇转化为 dl-形式时得到了验证。邻近醚氧原子的 CH 中心在硫醇催化下的缩合反应要比邻近酰胺氮原子的类似中心快得多，这一结果可以从极性效应对亲电巯基取氢速率的重要性角度来理解。
• Synthesis of triazolopyrimidine compounds
  申请人：LEK Pharmaceuticals d.d.

  公开号：EP2607355A1

  公开（公告）日：2013-06-26

  The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

  本发明涉及有机合成领域，描述了合成特定中间体的方法，该中间体适用于制备三唑并嘧啶化合物，例如替卡格雷。
• MACROCYCLIC PROLINE DERIVED HCV SERINE PROTEASE INHIBITORS
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US20140194350A1

  公开（公告）日：2014-07-10

  The present invention discloses compounds of Formula I or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明披露了I式化合物或其药学上可接受的盐、酯或前药：其抑制丝氨酸蛋白酶活性，特别是丙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰了丙型肝炎病毒的生命周期，也可用作抗病毒剂。本发明还涉及包含上述化合物的制药组合物，用于治疗患有HCV感染的受试者。本发明还涉及通过给予包含本发明化合物的制药组合物来治疗受试者的HCV感染的方法。
• IMPROVED NUCLEIC ACID LIPID PARTICLE FORMULATIONS
  申请人：ALNYLAM PHARMACEUTICALS, INC.

  公开号：US20150306039A1

  公开（公告）日：2015-10-29

  The present invention relates to lipid nanoparticles containing a biodegradable cationic lipid which provide improved delivery of active pharmaceutical ingredients, such as siRNA.
• US9220748B2
  申请人：——

  公开号：US9220748B2

  公开（公告）日：2015-12-29