3-((1R)-1-phenylethyl)-6-chloro-4-phenyl-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-((1R)-1-phenylethyl)-6-chloro-4-phenyl-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one
• 英文别名: (4S)-6-chloro-4-phenyl-3-[(1R)-1-phenylethyl]-4-(trifluoromethyl)-1H-quinazolin-2-one
• 化学式: C₂₃H₁₈ClF₃N₂O
• 分子量: 430.857
• InChiKey: BIGKYVKCBZSBCN-QRQCRPRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-(+)-1-苯乙基异氰酸酯 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 3-((1R)-1-phenylethyl)-6-chloro-4-phenyl-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one
  参考文献：
  名称：

  General Scope of 1,4-Diastereoselective Additions to a 2(3H)-Quinazolinone:  Practical Preparation of HIV Therapeutics

  摘要：

  The practical and highly diastereoselective syntheses of CF3-substituted dihydroquinazolinones via 1,4-additions of nucleophiles to chiral auxiliary substituted 2(3H)-quinazolinones is described. This methodology is applied to the syntheses of the NNRTIs (nonnucleoside reverse transcriptase inhibitors) DPC 961 (1) and DPC 083 (2), which are useful for the treatment of HIV (human immunodeficiency virus). The synthesis of DPC 961 (1) requires three steps, proceeds in >55% overall yield from the keto-aniline 9, and gives synthetic access to DPC 083 (2). In addition, the scope of the new diastereoselective 1,4-addition chemistry is investigated. The first preparation of DPC 961 (1) described in this paper is a derivatization fractional crystallization protocol.

  DOI：

  10.1021/jo0263162

文献信息

• General Scope of 1,4-Diastereoselective Additions to a 2(3<i>H</i>)-Quinazolinone:  Practical Preparation of HIV Therapeutics
  作者：Nicholas A. Magnus、Pat N. Confalone、Louis Storace、Mona Patel、Christopher C. Wood、Wayne P. Davis、Rodney L. Parsons

  DOI：10.1021/jo0263162

  日期：2003.2.1

  The practical and highly diastereoselective syntheses of CF3-substituted dihydroquinazolinones via 1,4-additions of nucleophiles to chiral auxiliary substituted 2(3H)-quinazolinones is described. This methodology is applied to the syntheses of the NNRTIs (nonnucleoside reverse transcriptase inhibitors) DPC 961 (1) and DPC 083 (2), which are useful for the treatment of HIV (human immunodeficiency virus). The synthesis of DPC 961 (1) requires three steps, proceeds in >55% overall yield from the keto-aniline 9, and gives synthetic access to DPC 083 (2). In addition, the scope of the new diastereoselective 1,4-addition chemistry is investigated. The first preparation of DPC 961 (1) described in this paper is a derivatization fractional crystallization protocol.