(Z)-(R)-N-Boc-2-amino-4-phenyl-3-butenol | 132682-38-3

• 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: (Z)-(R)-N-Boc-2-amino-4-phenyl-3-butenol
• 英文别名: tert-butyl N-[(Z,2R)-1-hydroxy-4-phenylbut-3-en-2-yl]carbamate
• CAS: 132682-38-3
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: ZQOCCWDEZIXAJE-ASCRHOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-N-Boc-2-amino-4-phenyl-3-butenol 在 盐酸 、 四氧化锇 、 N-甲基吲哚酮 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 丙酮 、 乙腈 为溶剂， 反应 45.0h， 生成 (1S,2R,3S)-dodecanoic acid (2,3-dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-amide
  参考文献：
  名称：

  Stereoselective Synthesis and Structure−Activity Relationship of Novel Ceramide Trafficking Inhibitors. (1R,3R)-N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and Its Analogues

  摘要：

  New ceramide trafficking inhibitors, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) and a series of its analogues, were synthesized in diastereomerically and enantiomerically pure forms, and the structure-activity relationship was investigated. These analogues were stereoselectively synthesized via catalytic enantioselective Mannich-type reactions using a Cu(II)-chiral diamine 4 complex. Analysis of HPA-12 analogues having various lengths of the amide side chain showed that the optimal chain length for the inhibition of sphingomyelin biosynthesis is 13 with an IC50 of similar to50 nM. Masking of the hydroxy group at the 2'- or 3-position of HPA-12 was carried out by methylation, and it was revealed that these hydroxy groups were essential for the activity. Installation of another hydroxy group onto HPA-12 at the same position as that in the natural ceramide was also conducted, but no enhancement of the activity was observed.

  DOI：

  10.1021/jm0300779
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 Amberlite IR-120 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 20.5h， 生成 (Z)-(R)-N-Boc-2-amino-4-phenyl-3-butenol
  参考文献：
  名称：

  使用不对称二羟基化技术快速有效地合成植物鞘氨醇

  摘要：

  描述了通过使用衍生自1-丝氨酸的旋光性烯烃的不对称二羟基化来简短合成植物鞘氨醇衍生物及其立体异构体。

  DOI：

  10.1016/s0040-4020(98)00615-2

文献信息

• Synthesis of chiral vinylglycines
  作者：Pierre L. Beaulieu、Jean Simon Duceppe、Carolyne Johnson

  DOI：10.1021/jo00013a023

  日期：1991.6

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.
• A new nucleophilic alaninol synthon from serine
  作者：Mukund P. Sibi、Paul A. Renhowe

  DOI：10.1016/s0040-4039(00)88501-9

  日期：1990.1

  A new nucleophilic alaninol synthon derived from serine is reported. The utility of this reagent in the stereoselective synthesis of beta,gamma-unsaturated amino alcohols is described.