(-)-N-((1S,2S)-2-hydroxy-1-phenyl-3-butenyl)benzamide | 136693-02-2

• 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-((1S,2S)-2-hydroxy-1-phenyl-3-butenyl)benzamide
• 英文别名: N-[(1S,2S)-2-hydroxy-1-phenylbut-3-enyl]benzamide
• CAS: 136693-02-2
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: OQLKLXPKPPPXDZ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-N-((1S,2S)-2-hydroxy-1-phenyl-3-butenyl)benzamide 、 乙烯基乙醚 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到N-[(1S,2S)-2-(1-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide
  参考文献：
  名称：

  Direct, highly efficient synthesis from (S)-(+)-phenylglycine of the taxol and taxotere side chains

  摘要：

  DOI：

  10.1021/jo00024a044
• 作为产物：
  描述：

  (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (-)-N-((1S,2S)-2-hydroxy-1-phenyl-3-butenyl)benzamide
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r

文献信息

• Lipase-Catalyzed Kinetic Resolution of 4-(<i>N</i>-Boc-amino)-1-alken-3-ols
  作者：Tadakatsu Mandai、Tetsuta Oshitari

  DOI：10.1055/s-2003-42115

  日期：——

  A wide range of 4-(N-Boc-amino)-1-alken-3-ols were efficiently resolved by lipase-catalyzed kinetic resolution. This procedure has been successfully applied to the highly enantioselective synthesis of the taxol side chain.

  脂肪酶催化的动力学拆分有效地拆分了范围广泛的 4-(N-Boc-amino)-1-alken-3-ols。该程序已成功应用于紫杉醇侧链的高度对映选择性合成。
• US9493436B2
  申请人：——

  公开号：US9493436B2

  公开（公告）日：2016-11-15
• Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)
  作者：Kee-Young Lee、Yong-Hyun Kim、Min-Sung Park、Chang-Young Oh、Won-Hun Ham

  DOI：10.1021/jo991065r

  日期：1999.12.1

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.
• Direct, highly efficient synthesis from (S)-(+)-phenylglycine of the taxol and taxotere side chains
  作者：Jean Noel Denis、Arlene Correa、Andrew E. Greene

  DOI：10.1021/jo00024a044

  日期：1991.11