(R)-3-(2-phenylethyl)-3-[(4-phenylphenoxy)methoxy]hexanol | 215317-11-6

• 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: (R)-3-(2-phenylethyl)-3-[(4-phenylphenoxy)methoxy]hexanol
• 英文别名: (3R)-3-(2-phenylethyl)-3-[(4-phenylphenoxy)methoxy]hexan-1-ol
• CAS: 215317-11-6
• 化学式: C₂₇H₃₂O₃
• 分子量: 404.549
• InChiKey: JOJIETQASLPADP-HHHXNRCGSA-N

物化性质

• 熔点：
  49-53 °C
• 沸点：
  574.0±50.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(2-phenylethyl)-3-[(4-phenylphenoxy)methoxy]hexanol 在 palladium on activated charcoal sodium hydroxide 、 sodium hypochlorite 、 florisil 、 阻聚剂701 、 硫酸 、 氢气 、 sodium acetate 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 pyridinium chlorochromate 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， -90.0~25.0 ℃ 、344.73 kPa 条件下， 反应 133.0h， 生成 替拉那韦
  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：

  3-羟基-3-(2-苯基乙基)己酸 在 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (R)-3-(2-phenylethyl)-3-[(4-phenylphenoxy)methoxy]hexanol
  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

• Process to produce a protease inhibitor
  申请人：Pharmacia & Upjohn Company

  公开号：US06077963A1

  公开（公告）日：2000-06-20

  Disclosed is a novel process and novel intermediates to prepare [R-(R*,R*)]-N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propy l-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide (XIX) ##STR1## which is a protease inhibitor useful in treating humans infected with the HIV virus.

  揭示了一种新颖的过程和新颖的中间体，用于制备[R-(R*，R*)]-N-[3-[1-[5,6-二氢-4-羟基-2-氧代-6-(2-苯乙基)-6-丙基-2H-吡喃-3-基]丙基]苯基]-5-(三氟甲基)-2-吡啶磺酰胺（XIX），该化合物是一种蛋白酶抑制剂，用于治疗感染HIV病毒的人类。
• (R)-3-hydroxy-3-(2-phenylethyl)-hexanoic acid derivatives
  申请人：Pharmacia & Upjohn Company

  公开号：US06265604B1

  公开（公告）日：2001-07-24

  The compound of the present invention (R)-3-hydroxy-3-(2-phenylethyl)-hexanoic acid is an intermediate in the preparation of the anti-AIDS compound, [R-(R*,R*)]-N-[3-[1-5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide.

  本发明中的化合物(R)-3-羟基-3-(2-苯乙基)-己酸是制备抗艾滋病化合物[R-(R*，R*)]-N-[3-[1-5,6-二氢-4-羟基-2-氧代-6-(2-苯乙基)-6-丙基-2H-吡喃-3-基]丙基]苯基-5-(三氟甲基)-2-吡啶磺酰胺的中间体。
• J. Org. Chem. 1998, 63, 7348-7356
  作者：

  DOI：——

  日期：——
• DEUTERIUM-ENRICHED TIPRANAVIR
  申请人：Czarnik Anthony W.

  公开号：US20090062346A1

  公开（公告）日：2009-03-05

  The present application describes deuterium-enriched tipranavir, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
• 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.