甲基(4R,5R)-5-甲基-4,5-二氢-1,3-恶唑-4-羧酸酯 | 104320-71-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基(4R,5R)-5-甲基-4,5-二氢-1,3-恶唑-4-羧酸酯
• 中文别名: 4-噁唑羧酸,4,5-二氢-5-甲基-,甲基酯,(4R-顺)-(9CI)
• 英文名称: Methyl (4R,5R)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 104320-71-0
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: RAAGHFMDHMDDNX-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 allo-Thr-OMe 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 甲基(4R,5R)-5-甲基-4,5-二氢-1,3-恶唑-4-羧酸酯
  参考文献：
  名称：

  Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium Leptolyngbya sp.

  摘要：

  Coibamide A (1) is a new, potent antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium collected from the Coiba National Park, Panama. The planar structure of I was elucidated by a combination of NMR spectroscopy and mass spectrometry. Exhaustive 1 D and 2D NMR spectroscopy included natural abundance (15)N and variable temperature experiments; mass spectrometry included TOF-ESI-MS(n) and FT-MS(n) experiments, Chemical degradation followed by chiral HPLC- and GC-MS analyses was used to assign the absolute configuration of 1. This highly methylated cyclized depsipeptide exhibited an unprecedented selectivity profile in the NCl 60 cancer cell line panel and appears to act via a novel mechanism.

  DOI：

  10.1021/ja801383f

文献信息

• Asymmetric aldol reaction of an isocyanoacetate with aldehydes bychiral ferrocenylphosphine-gold(I) complexes: Design and preparation of new efficient ferrocenylphosphine ligands
  作者：Yoshihiko Ito、Masaya Sawamura、Tamio Hayashi

  DOI：10.1016/s0040-4039(00)61850-6

  日期：1987.1

  optically active ferrocenylphosphine ligand containing 2-(morpholino)ethylamino or 2-(piperidino)ethylamino group on the ferrocene side chain was effective for the gold-catalyzed aldol reaction of methyl isocyanoacetate with aldehydes to give optically active 4-methoxycarbonyl-5-alkyl-2-oxazolines (up to 96% ee) with high enantio- and diastereoselectivity in a quantitative yield.

  在二茂铁侧链上含有2-（吗啉代）乙基氨基或2-（哌啶子基）乙基氨基的光学活性二茂铁基膦配体对于金催化的异氰基乙酸甲酯与醛的醛醇缩合反应产生光学活性的4-甲氧基羰基-5-烷基是有效的。具有高对映体和非对映体选择性的-2-恶唑啉（高达96％ee），定量收率。
• Catalytic asymmetric aldol reaction: reaction of aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex
  作者：Yoshihiko. Ito、Masaya. Sawamura、Tamio. Hayashi

  DOI：10.1021/ja00280a056

  日期：1986.10