(S)-1-(2-chloroethoxy)-3-chloropropan-2-ol | 861852-07-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S)-1-(2-chloroethoxy)-3-chloropropan-2-ol
• 英文别名: (2S)-1-chloro-3-(2-chloroethoxy)propan-2-ol
• CAS: 861852-07-5
• 化学式: C₅H₁₀Cl₂O₂
• 分子量: 173.039
• InChiKey: TWIWQIMWZBPIGB-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-chloroethoxy)-3-chloropropan-2-ol 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 (2R)-1,4-dioxan-2-yl-N-methylmethanaminium chloride
  参考文献：
  名称：

  Process Development and Large-Scale Synthesis of a c-Met Kinase Inhibitor

  摘要：

  A highly convergent synthesis of c-Met kinase inhibitor 1 has been demonstrated on a multikilogram scale using three key fragments: dihalotricyclic core 2, chiral sulfamide side chain 3, and pyrazole boronic ester 4. The chirality in sulfamide side chain 3 was installed using the cheap and readily available starting material (S)epichlorohydrin. A total of 2.71 kg of 1 were isolated in seven steps (the longest linear sequence).

  DOI：

  10.1021/op100101q
• 作为产物：
  描述：

  右旋环氧氯丙烷 、 2-氯乙醇 在 三氟化硼乙醚 作用下， 反应 1.5h， 以100%的产率得到(S)-1-(2-chloroethoxy)-3-chloropropan-2-ol
  参考文献：
  名称：

  基于二恶烷的抗病毒剂的合成及其作为Sindbis病毒复制抑制剂的生物活性的评估。

  摘要：

  Sindbis病毒衣壳蛋白的晶体结构在疏水结合口袋中包含一个或两个溶剂衍生的二恶烷分子。通过将两个二氧六环分子与具有连接立体化学的R，R的三碳链连接，设计了双二氧六环抗病毒剂，并进行了立体特异性合成。这导致了一种有效的抗病毒剂，以14 microM的EC（50）抑制了Sindbis病毒的复制。合成过程通过中间体（R）-2-羟甲基-[1,4]二恶烷进行，该化合物出乎意料地证明是比目标化合物更有效的抗病毒剂，其EC（50）为3.4 microM作为抑制剂证明了这一点。 Sindbis病毒复制。两种化合物在浓度为1mM的未感染BHK细胞中均无细胞毒性。

  DOI：

  10.1016/j.bmc.2007.01.040

文献信息

• Design, synthesis, and evaluation of dioxane-based antiviral agents targeted against the Sindbis virus capsid protein
  作者：Ha Young Kim、Chinmay Patkar、Ranjit Warrier、Richard Kuhn、Mark Cushman

  DOI：10.1016/j.bmcl.2005.05.013

  日期：2005.7

  Dioxane-based antiviral agents targeted to the hydrophobic binding pocket of Sindbis virus capsid protein were designed by computer graphics molecular modeling and synthesized. Virus production using SIN-IRES-Lue and capsid assembly were monitored to evaluate antiviral activity. A compound with a three-carbon linker chain connecting two dioxane moieties inhibited virus production by 50% at a concentration of 40 mu M, while (R)-hydroxymethyldioxane inhibited virus production by 50% at a concentration of 1 mu M. Both compounds were not cytotoxic in uninfected BHK cells at concentrations of 1 mM. (c) 2005 Elsevier Ltd. All rights reserved.
• Process Development and Large-Scale Synthesis of a c-Met Kinase Inhibitor
  作者：Gavin W. Stewart、Karel M. J. Brands、Sarah E. Brewer、Cameron J. Cowden、Antony J. Davies、John S. Edwards、Andrew W. Gibson、Simon E. Hamilton、Jason D. Katz、Stephen P. Keen、Peter R. Mullens、Jeremy P. Scott、Debra J. Wallace、Christopher S. Wise

  DOI：10.1021/op100101q

  日期：2010.7.16

  A highly convergent synthesis of c-Met kinase inhibitor 1 has been demonstrated on a multikilogram scale using three key fragments: dihalotricyclic core 2, chiral sulfamide side chain 3, and pyrazole boronic ester 4. The chirality in sulfamide side chain 3 was installed using the cheap and readily available starting material (S)epichlorohydrin. A total of 2.71 kg of 1 were isolated in seven steps (the longest linear sequence).
• Synthesis of dioxane-based antiviral agents and evaluation of their biological activities as inhibitors of Sindbis virus replication
  作者：Ha Young Kim、Richard J. Kuhn、Chinmay Patkar、Ranjit Warrier、Mark Cushman

  DOI：10.1016/j.bmc.2007.01.040

  日期：2007.4

  solvent-derived dioxane molecules in the hydrophobic binding pocket. A bis-dioxane antiviral agent was designed by linking the two dioxane molecules with a three-carbon chain having R,R connecting stereochemistry, and a stereospecific synthesis was performed. This resulted in an effective antiviral agent that inhibited Sindbis virus replication with an EC(50) of 14 microM. The synthesis proceeded through

  Sindbis病毒衣壳蛋白的晶体结构在疏水结合口袋中包含一个或两个溶剂衍生的二恶烷分子。通过将两个二氧六环分子与具有连接立体化学的R，R的三碳链连接，设计了双二氧六环抗病毒剂，并进行了立体特异性合成。这导致了一种有效的抗病毒剂，以14 microM的EC（50）抑制了Sindbis病毒的复制。合成过程通过中间体（R）-2-羟甲基-[1,4]二恶烷进行，该化合物出乎意料地证明是比目标化合物更有效的抗病毒剂，其EC（50）为3.4 microM作为抑制剂证明了这一点。 Sindbis病毒复制。两种化合物在浓度为1mM的未感染BHK细胞中均无细胞毒性。