4-benzyl-2-(2,6-dimethoxyphenyl)-4H-1,3-oxazol-5-one | 1412899-23-0

• 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
• 英文名称: 4-benzyl-2-(2,6-dimethoxyphenyl)-4H-1,3-oxazol-5-one
• CAS: 1412899-23-0
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: OSBOCFZCTOOLDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyl-2-(2,6-dimethoxyphenyl)-4H-1,3-oxazol-5-one 在 (3S,5S,8S)-2,2,7,7-tetrakis(4-fluorophenyl)-4,9-dimethyl-3,8-bis(2-methylpropyl)-1,4,6,9-tetraza-5lambda5-phosphaspiro[4.4]non-1(5)-ene 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles

  摘要：

  A vinylog of Michael addition (1,6-addition) of azlactones to delta-substituted dienyl N-acylpyrroles been developed with virtually complete 1,6-diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8 addition) of azlactones to zeta-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.

  DOI：

  10.1021/ja310209g

文献信息

• Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis
  作者：Ken Yoshioka、Kohei Yamada、Daisuke Uraguchi、Takashi Ooi

  DOI：10.1039/c7cc01715d

  日期：——

  and enantioselective 1,6-addition of azlactone to various alkenyl dienyl ketones has been achieved under P-spiro chiral triaminoiminophosphorane catalysis. This site-selectivity control relies on the distinct ability of the conjugate acids of iminophosphoranes, aminophosphonium ions, to precisely differentiate between the three electrophilic reaction sites of alkenyl dienyl ketones, which is further demonstrated

  在P-螺环手性三氨基亚氨基正膦催化下，将内酯向多种烯基二烯基酮进行高度区域，非对映和对映选择性的1,6-加成反应。这种位点选择性控制依赖于亚氨基正膦酸酯，氨基离子的共轭酸在烯基二烯基酮的三个亲电反应位点之间精确区分的独特能力，这进一步通过区分性不对称的1，6-添加add内酯来证明。二烯基酮，保留完整存在的烯基酮。
• Catalyst‐Enabled Site‐Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors
  作者：Daisuke Uraguchi、Ryo Shibazaki、Naoya Tanaka、Kohei Yamada、Ken Yoshioka、Takashi Ooi

  DOI：10.1002/anie.201800057

  日期：2018.4.16

  distinct catalysts. Cinchonidine‐derived thiourea catalyzes the 1,4‐addition of prochiral azlactone enolates to enynyl N‐acyl pyrazoles in a highly diastereo‐ and enantioselective manner to give stereochemically defined alkynes, while P‐spiro chiral triaminoiminophosphorane catalytically controls the stereoselective 1,6‐addition and the consecutive γ‐protonation of the vinylogous enolate intermediate

  基于两种不同催化剂的鉴定，开发了位点立体选择性迈克尔反应系统。辛可尼定衍生的硫脲以非对映和对映选择性的方式催化前手性氮杂内酯与烯丙基N-酰基吡唑的1,4-加成反应，生成立体化学定义的炔烃，而P-螺环手性三氨基亚氨基正膦催化催化控制立体选择性的1,6-以及乙烯醇烯酸酯中间体的连续γ质子化作用，以提供Z，E构型的共轭二烯。该1,6-加合物是合成2-氨基-2-脱氧糖的有价值的前体。
• Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl <i>N</i>-Acylpyrroles
  作者：Daisuke Uraguchi、Ken Yoshioka、Yusuke Ueki、Takashi Ooi

  DOI：10.1021/ja310209g

  日期：2012.11.28

  A vinylog of Michael addition (1,6-addition) of azlactones to delta-substituted dienyl N-acylpyrroles been developed with virtually complete 1,6-diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8 addition) of azlactones to zeta-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.