(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole | 1006588-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole
• 英文别名: (4R,5S)-4,5-indandiyloxazoline；(3aS,8bR)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazole
• CAS: 1006588-66-4
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: KAXVGRDUHDKATO-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole 在 叔丁基锂 、 1,1,2,2-四氟-1,2-二溴乙烷 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 以32%的产率得到(4R,5S)-2-bromo-4,5-indanediyloxazoline
  参考文献：
  名称：

  Thermal Rearrangement of 2-Bromooxazolines to 2-Bromoisocyanates

  摘要：

  A unprecedented thermally induced rearrangement of 2-bromo-4-substituted oxazolines into 2-bromoisocyanates with high selectivity has been observed. Isolated yields of 85-90% were obtained with 2-bromo-4-phenyloxazoline, 2-bromo-4-isopropyloxazoline, or 2-bromo-4,4dimethyloxazoline. In addition, chiral aziridinecarboxamdes or 2-aminooxazolines could be selectively obtained from the corresponding 2-bromo isocyanate depending on reaction conditions.

  DOI：

  10.1021/ol7027509

文献信息

• Highly Efficient and Versatile Pd-Catalyzed Direct Alkynylation of Both Azoles and Azolines
  作者：Seok Hwan Kim、Sukbok Chang

  DOI：10.1021/ol100488v

  日期：2010.4.16

  A highly efficient and versatile Pd-catalyzed direct alkynylation reaction of heterocycles with 1-bromoalkynes was developed. The substrate scope of the reaction was very broad to include not only azoles but also azolines for the first time, thus offering an important advance in the direct functionalization of heterocycles.

  开发了一种高效且通用的Pd催化杂环与1-溴代炔烃的直接炔基化反应。反应的底物范围非常广泛，首次不仅包括唑类，而且还包括偶氮类，因此在杂环的直接官能化方面提供了重要的进展。
• Ti(O<i>i</i>Pr)₄-Mediated Multicomponent Reactions Involving Triple Additions to Isonitrile Carbon Atoms
  作者：Francesco Foschi、Torsten Roth、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/acs.orglett.6b02746

  日期：2016.10.7

  Double addition of Grignard reagents to isonitriles was achieved in the presence of stoichiometric amounts of [Ti(OiPr)4]. Functionalized isonitrile components were obtained in situ via lithiation of chiral and achiral 2-oxazolines, and the resulting amidomethyltitanium intermediate further reacted with a range of electrophiles. The established multicomponent procedure gave rise to highly substituted

  在化学计量的[Ti（O i Pr）4 ]存在下，将格氏试剂双加到异腈中。通过手性和非手性2-恶唑啉的锂化原位获得官能化的异腈组分，并且所得的酰胺基甲基钛中间体进一步与一系列亲电试剂反应。既定的多组分方法通过简单的合成方法产生了高度取代的2-氨基吗啉，无环二氨基醇和异戊烯基化的氨基醇。