1-Chloro-4-[(4-phenylphenoxy)methylsulfanyl]benzene | 215316-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Chloro-4-[(4-phenylphenoxy)methylsulfanyl]benzene
• CAS: 215316-99-7
• 化学式: C₁₉H₁₅ClOS
• 分子量: 326.846
• InChiKey: WSDRGQITBWEKQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Chloro-4-[(4-phenylphenoxy)methylsulfanyl]benzene 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.18h， 生成 (R)-(4-苯基苯氧基)甲基-3-(2-苯基乙基)-3-[(4-苯基苯氧基)甲氧基]己酸酯
  参考文献：
  名称：

  A Convergent, Scalable Synthesis of HIV Protease Inhibitor PNU-140690

  摘要：

  PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evalution as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.

  DOI：

  10.1021/jo9809229
• 作为产物：
  描述：

  对羟基联苯 、 (bromomethyl)(4-chlorophenyl)sulfane 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以83.2%的产率得到1-Chloro-4-[(4-phenylphenoxy)methylsulfanyl]benzene
  参考文献：
  名称：

  A Convergent, Scalable Synthesis of HIV Protease Inhibitor PNU-140690

  摘要：

  PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evalution as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.

  DOI：

  10.1021/jo9809229

文献信息

• A Convergent, Scalable Synthesis of HIV Protease Inhibitor PNU-140690
  作者：Kristina S. Fors、James R. Gage、Richard F. Heier、Robert C. Kelly、William R. Perrault、Nancy Wicnienski

  DOI：10.1021/jo9809229

  日期：1998.10.1

  PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evalution as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.