2-(benzo[b]thiophen-3-yl)-4-tert-butyl-4,5-dihydrooxazole | 497866-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(benzo[b]thiophen-3-yl)-4-tert-butyl-4,5-dihydrooxazole
• 英文别名: (4S)-2-(1-benzothiophen-3-yl)-4-tert-butyl-4,5-dihydro-1,3-oxazole
• CAS: 497866-80-5
• 化学式: C₁₅H₁₇NOS
• 分子量: 259.372
• InChiKey: OFBNHUXHSKUNFN-CYBMUJFWSA-N

物化性质

• 沸点：
  390.7±15.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二苯基氯化膦 、 2-(benzo[b]thiophen-3-yl)-4-tert-butyl-4,5-dihydrooxazole 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以89%的产率得到2-[2-(diphenylphosphino)benzo[b]thiophen-3-yl]-4-tert-butyl-4,5-dihydrooxazole
  参考文献：
  名称：

  新型手性噻吩-、苯并噻吩-和苯并呋喃-恶唑啉配体的合成及其在对映选择性 Pd 催化烯丙基化中的应用

  摘要：

  在杂环骨架的不同位置含有二苯基膦基的新型噻吩、苯并噻吩和苯并呋喃-恶唑啉配体 6-11 已被制备并用于对映选择性烯丙基化。这些新配体的优点是易于获取和高反应性。用配体9获得了最好的结果，在0°C下2小时内以97.0% ee得到产物13，产率为92%。

  DOI：

  10.1055/s-2002-35577
• 作为产物：
  描述：

  1-苯并噻吩-3-羧酸 在 氢氧化钾 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 2-(benzo[b]thiophen-3-yl)-4-tert-butyl-4,5-dihydrooxazole
  参考文献：
  名称：

  新型手性噻吩-、苯并噻吩-和苯并呋喃-恶唑啉配体的合成及其在对映选择性 Pd 催化烯丙基化中的应用

  摘要：

  在杂环骨架的不同位置含有二苯基膦基的新型噻吩、苯并噻吩和苯并呋喃-恶唑啉配体 6-11 已被制备并用于对映选择性烯丙基化。这些新配体的优点是易于获取和高反应性。用配体9获得了最好的结果，在0°C下2小时内以97.0% ee得到产物13，产率为92%。

  DOI：

  10.1055/s-2002-35577

文献信息

• Isoxazoline derivatives as p n ligands
  申请人：——

  公开号：US20040171841A1

  公开（公告）日：2004-09-02

  The invention relates to novel ligands of the phosphanylbenzothiophenyl-dihydroisoxazoline, phosphanyl-dihydrooxazolyl-indole and phosphanyl-dihydrooxazolyl-benzofuran type, especially compounds of formula I 1 and mixtures of such compounds, wherein X is oxygen, sulfur, selenium or NQ, wherein Q is unsubstituted or substituted aryl, or alkyl or substituted alkyl; n is 0, 1, 2, 3 or 4; A 1 and A 2 are each an organic radical capable of bonding to phosphorus, especially unsubstituted or substituted alkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted cycloalkyl, or —N(D) 2 wherein D 2 is alkyl or substituted alkyl; or A 1 and A 2 together with the bonding phosphorus atom form a ring, which may be unsubstituted or substituted; Y, Y′, Y″ and Y′″ are each independently of the other hydrogen or alkyl, substituted alkyl, unsubstituted or substituted aryl, or unsubstituted or substituted heterocyclyl, at least one of the radicals Y, Y′, Y″ or Y′″ being one of the mentioned radicals with the exception of hydrogen; and Z, when present, is a substituent, it being possible when a plurality of substituents Z is present for those substituents to be selected independently of one another, and to processes for their preparation, to novel precursors and intermediates, to complexes with the said ligands, to their preparation and to their use as catalysts in organic synthesis (especially asymmetric organic synthesis).

  本发明涉及膦酰基苯并噻吩基二氢异噁唑啉、膦酰基二氢噁唑基吲哚和膦酰基二氢噁唑基苯并呋喃类型的新型配体，特别是式 I 的化合物 1 以及这类化合物的混合物，其中 X 是氧、硫、硒或 NQ，其中 Q 是未取代或取代的芳基，或烷基或取代的烷基； n 是 0、1、2、3 或 4； A 1 和 A 2 各自是能与磷键合的有机基，特别是未取代或取代的烷基、未取代或取代的芳基、未取代或取代的杂环基、未取代或取代的环烷基或 -N(D) 2 其中 D 2 是烷基或取代的烷基；或 A 1 和 A 2 与结合的磷原子一起形成一个环，该环可以是未取代的或取代的； Y、Y′、Y″和 Y′″各自独立地为氢或烷基、取代烷基、未取代或取代芳基、未取代或取代杂环基，Y、Y′、Y″或 Y′″中至少有一个基为上述基之一，但氢除外；以及 Z，当存在时，是一个取代基，当存在多个取代基 Z 时，这些取代基可以彼此独立地选择，并可用于制备它们的工艺、新型前体和中间体、与所述配体的络合物、它们的制备以及它们在有机合成（特别是不对称有机合成）中作为催化剂的使用。
• ISOXAZOLINE DERIVATIVES AS P, N LIGANDS
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1419165A1

  公开（公告）日：2004-05-19
• [EN] ISOXAZOLINE DERIVATIVES AS P, N LIGANDS<br/>[FR] DERIVES D'ISOXAZOLINE SOUS FORME DE P, N LIGANDS
  申请人：CIBA SC HOLDING AG

  公开号：WO2003014133A1

  公开（公告）日：2003-02-20

  The invention relates to novelligands of the phosphanylbenzothiophenyl-dihydroisoxazoline, phosphanyl-dihydrooxazolyl-indole and phosphanyl-dihydrooxazolyl-benzofuran type, especially compounds of formula (I) and mixtures of such compounds, wherein X is oxygen, sulfur, selenium or NO, wherein a is unsubstituted or substituted aryl, or alkyl or substituted alkyl and to processes for their preparation, to novel precursors and intermediates, to complexes with the said ligands, to their preparation and to their use as catalysts in organic synthesis (especially asymmetric organic synthesis).
• Synthesis of Novel Chiral Thiophene-, Benzothiophene- and Benzofuran-Oxazoline Ligands and their Use in the Enantioselective Pd-Catalyzed Allylation
  作者：Lutz F. Tietze、J. Klaas Lohmann

  DOI：10.1055/s-2002-35577

  日期：——

  benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0 °C.

  在杂环骨架的不同位置含有二苯基膦基的新型噻吩、苯并噻吩和苯并呋喃-恶唑啉配体 6-11 已被制备并用于对映选择性烯丙基化。这些新配体的优点是易于获取和高反应性。用配体9获得了最好的结果，在0°C下2小时内以97.0% ee得到产物13，产率为92%。
• HetPHOX: a new class of easily prepared modular chiral ligands
  作者：Nicole End、Catherine Stoessel、Ulrich Berens、Pierino di Pietro、Pier Giorgio Cozzi

  DOI：10.1016/j.tetasy.2004.06.014

  日期：2004.7

  The synthesis of a new class of modular chiral phosphino-oxazoline ligands containing the diphenylphosphino group at different positions of the heterocyclic backbone is described. HetPHOX ligands were tested in enantioselective allylations and in transfer hydrogenation reactions. The synthesis of the ligands is facile with high enantioselectivity (99% ee) obtained in the Pd-catalyzed addition of malonate to diphenylallyl acetate using ligand 10. (C) 2004 Elsevier Ltd. All rights reserved.