(4S)-4-isopropyl-2-(3,4,5-trimethoxyphenyl)-2-oxazoline | 848477-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S)-4-isopropyl-2-(3,4,5-trimethoxyphenyl)-2-oxazoline
• 英文别名: (S)-4-isopropyl-2-(3,4,5-trimethoxyphenyl)-4,5-dihydrooxazole；(4S)-4-propan-2-yl-2-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,3-oxazole
• CAS: 848477-24-7
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: SPUGCMWMSUKARH-LLVKDONJSA-N

物化性质

• 沸点：
  389.8±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

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：
  0.53
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-isopropyl-2-(3,4,5-trimethoxyphenyl)-2-oxazoline 在 仲丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.25h， 生成 (S,Z)-2-(1-heptyl-5,6,7-trimethoxyisobenzofuran-3(1H)-ylideneamino)-3-methylbutan-1-ol
  参考文献：
  名称：

  Cytosporone E: racemic synthesis and preliminary antibacterial testing

  摘要：

  The antibiotic cytosporone E (isolated from the broth of the endophytic fungi CR 200 (Cytospora sp.) and CR 146 (Diaporthe sp.)) was synthesized as a racemic mixture. The key step in the synthesis is the Meyers ortho-alkylation of a chiral aromatic oxazoline. Preliminary antibiotic activity shows antibiosis against Gram-positive bacteria but not Gram-negative bacteria as previously reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.018
• 作为产物：
  描述：

  N-((S)-1-hydroxy-3-methylbutan-2-yl)-3,4,5-trimethoxybenzamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以97%的产率得到(4S)-4-isopropyl-2-(3,4,5-trimethoxyphenyl)-2-oxazoline
  参考文献：
  名称：

  Cytosporone E: racemic synthesis and preliminary antibacterial testing

  摘要：

  The antibiotic cytosporone E (isolated from the broth of the endophytic fungi CR 200 (Cytospora sp.) and CR 146 (Diaporthe sp.)) was synthesized as a racemic mixture. The key step in the synthesis is the Meyers ortho-alkylation of a chiral aromatic oxazoline. Preliminary antibiotic activity shows antibiosis against Gram-positive bacteria but not Gram-negative bacteria as previously reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.018

文献信息

• Direct Catalytic Asymmetric Cyclopropylphosphonation Reactions of <i>N,N</i>-Dialkyl Groups of Aniline Derivatives by Ru(II)-Pheox Complex
  作者：Chi Thi Loan Le、Seiya Ozaki、Soda Chanthamath、Kazutaka Shibatomi、Seiji Iwasa

  DOI：10.1021/acs.orglett.8b01788

  日期：2018.8.3

  N-methylaniline and asymmetric cyclopropylphosphonation reactions of N,N-diethylaniline derivatives with diazomethylphosphonates are reported. Optically active cyclopropylphosphonate derivatives were directly synthesized from diazomethylphosphonates and N,N-diethylaniline derivatives catalyzed by a Ru(II)-Pheox complex in one step in good yields and high diastereoselectivities (up to trans/cis = > 99:1<)

  报道了涉及N-甲基苯胺的膦酰基甲基化和N，N-二乙基苯胺衍生物与重氮甲基膦酸酯的不对称环丙基膦酸酯化反应的新型催化。光学活性的环丙基膦酸酯衍生物是直接由重氮甲基膦酸酯和N，N-二乙基苯胺衍生物经Ru（II）-Pheox络合物一步一步合成的，具有高收率和高非对映选择性（高达反式/顺式=> 99：1 <）和对映选择性（最高99％ee）。膦酰基甲基化和环丙基膦酰基化的D-标记机理研究表明，在反应过程中生成了烯胺或亚胺中间体。
• Aryl–aryl coupling via directed lithiation and oxidation
  作者：David S. Surry、David J. Fox、Simon J. F. Macdonald、David R. Spring

  DOI：10.1039/b501939g

  日期：——

  Aryl lithium reagents formed by directed lithiation reactions undergo transmetallation with copper(I) salts to form organocuprates, which may be efficiently oxidized to yield ortho-substituted biaryls.

  通过定向锂化反应形成的芳基锂试剂会与铜（I）盐发生金属转移，形成有机铜盐，可以有效地氧化生成邻位取代的联芳基。