N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene | 95832-30-7

• 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: N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene
• 英文别名: benzyl N-[(2R)-1-phenylbut-3-en-2-yl]carbamate
• CAS: 95832-30-7
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: GUBRGOFJDRRFAS-KRWDZBQOSA-N

物化性质

• 沸点：
  442.6±44.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene 在 钯 lithium hydroxide 、 sodium hydroxide 、 氢气 、 碘 、 silver(I) acetate 、 sodium 、 potassium hydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氨 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 乌苯美司
  参考文献：
  名称：

  碘代氨基甲酸酯从无环烯丙基胺立体控制合成（-）-贝斯他汀

  摘要：

  通过使用烯丙胺2和6描述了碘代氨基甲酸酯化反应的1,2-不对称诱导作用，该方法已成功地应用于Bestatin的立体控制合成中。

  DOI：

  10.1016/s0040-4039(01)91124-4
• 作为产物：
  描述：

  N-Cbz-D-苯丙氨醛 、 亚甲基三苯基膦烷 以 甲苯 为溶剂， 生成 N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene
  参考文献：
  名称：

  A Novel, Picomolar Inhibitor of Human Immunodeficiency Virus Type 1 Protease

  摘要：

  The design, synthesis, and molecular modeling studies of a novel series of azacyclic ureas, which are inhibitors of human immunodeficiency virus type 1 (HIV-1) protease that incorporate different ligands for the S1', S2, and S2' substrate-binding sites of HIV-1 protease are described. The synthesis of this series is highly flexible in the sense that the P1', P2, and P2' residues of the inhibitors can be changed independently. Molecular modeling studies on the phenyl ring of the P2 and P2' ligand suggested incorporation of hydrogen-bonding donor/acceptor groups at the 3' and 4-positions of the phenyl ring should increase binding potency. This led to the discovery of compound 7f (A-98881), which possesses high potency in the HIV-1 protease inhibition assay and the in vitro MT-4 cell culture assay (Ki = approximately 5 pM and EC50 = 0.002 microM). This compares well with the symmetrical cyclic urea 1 pioneered at DuPont Merck.

  DOI：

  10.1021/jm9507183

文献信息

• A novel process for the preparation of bestatin derivatives and intermediates thereof
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：EP0156279A2

  公开（公告）日：1985-10-02

  The present invention relates to a new method of preparing bestatin derivatives of the formula wherein Ph is an optionally substituted phenyl group and Leu represents a leucine residue, and to an intermediate of the formula where Ph is as defined above.

  本发明涉及一种制备式中 Ph 为任选取代的苯基和 Leu 代表亮氨酸残基的贝他丁衍生物的新方法，以及式中 Ph 如上定义的中间体。
• A Novel, Picomolar Inhibitor of Human Immunodeficiency Virus Type 1 Protease
  作者：Hing L. Sham、Chen Zhao、Kent D. Stewart、David A. Betebenner、Shuqun Lin、Chang H. Park、Xiang-P. Kong、William Rosenbrook、Thomas Herrin、Darold Madigan、Suthida Vasavanonda、Nicholas Lyons、Akhter Molla、Ayda Saldivar、Kennan C. Marsh、Edith McDonald、Norman E. Wideburg、Jon F. Denissen、Terrel Robins、Dale J. Kempf、Jacob J. Plattner、Daniel W. Norbeck

  DOI：10.1021/jm9507183

  日期：1996.1.1

  The design, synthesis, and molecular modeling studies of a novel series of azacyclic ureas, which are inhibitors of human immunodeficiency virus type 1 (HIV-1) protease that incorporate different ligands for the S1', S2, and S2' substrate-binding sites of HIV-1 protease are described. The synthesis of this series is highly flexible in the sense that the P1', P2, and P2' residues of the inhibitors can be changed independently. Molecular modeling studies on the phenyl ring of the P2 and P2' ligand suggested incorporation of hydrogen-bonding donor/acceptor groups at the 3' and 4-positions of the phenyl ring should increase binding potency. This led to the discovery of compound 7f (A-98881), which possesses high potency in the HIV-1 protease inhibition assay and the in vitro MT-4 cell culture assay (Ki = approximately 5 pM and EC50 = 0.002 microM). This compares well with the symmetrical cyclic urea 1 pioneered at DuPont Merck.
• A stereocontrolled synthesis of (−)-bestatin from an acyclic allylamine by iodocyclocarbamation
  作者：Susumu Kobayashi、Toshiyuki Isobe、Masaji Ohno

  DOI：10.1016/s0040-4039(01)91124-4

  日期：1984.1

  1,2-Asymmetric induction of iodocyclocarbamation is described by using allylamines 2 and 6 and the method has been successfully applied to a stereocontrolled synthesis of bestatin.

  通过使用烯丙胺2和6描述了碘代氨基甲酸酯化反应的1,2-不对称诱导作用，该方法已成功地应用于Bestatin的立体控制合成中。