(S)-2-(4-叔丁基-4,5-二氢噁唑-2-基)丙烷-2-醇 | 204333-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: (S)-2-(4-叔丁基-4,5-二氢噁唑-2-基)丙烷-2-醇
• 中文别名: (4S)-4-叔丁基-4,5-二氢-ALPHA,ALPHA-二甲基-2-恶唑甲醇
• 英文名称: (-)-(S)-2-[1'-Hydroxy-1'-methylethyl]-4-tert-butyloxazoline
• 英文别名: (S)-2-(dimethylhydroxy)methyl-4-tert-butyl-2-oxazoline；(-)-(S)-2-(4-tert-butyl-4,5-dihydrooxazol-2-yl)propan-2-ol；(-)-(S)-2-[2'-(hydroxy)prop-2'-yl]-4-tert-butyloxazoline；(S)-2-(4-(tert-Butyl)-4,5-dihydrooxazol-2-yl)propan-2-ol；2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-ol
• CAS: 204333-19-7
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: MNKXLAJVKRUKAN-SSDOTTSWSA-N

物化性质

• 熔点：
  86-87℃ (hexane )
• 沸点：
  241.4±23.0℃ (760 Torr)
• 密度：
  1.02±0.1 g/cm3 (20 ºC 760 Torr)
• 闪点：
  99.8±22.6℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-叔丁基-4,5-二氢噁唑-2-基)丙烷-2-醇 在 碘苯二乙酸 、 碘 、 palladium diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-4-tert-butyl-4,5-dihydro-2-(1-iodo-2-(tert-butyl(dimethyl)silyloxy)propan-2-yl)oxazole
  参考文献：
  名称：

  钯在温和条件下催化未活化CH键的不对称碘化。

  摘要：

  DOI：

  10.1002/anie.200462884
• 作为产物：
  描述：

  L-叔亮氨醇 在 triethyloxonium fluoroborate 作用下， 以 四氢呋喃 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 64.0h， 生成 (S)-2-(4-叔丁基-4,5-二氢噁唑-2-基)丙烷-2-醇
  参考文献：
  名称：

  Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes

  摘要：

  Starting either from benzoylformic acid or ethyl oxamate and enantiopure beta-amino alcohols, several chiral alpha-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.038

文献信息

• Chiral Bis(N-sulfonylamino)phosphine- and TADDOL-Phosphite-Oxazoline Ligands: Synthesis and Application in Asymmetric Catalysis
  作者：Robert Hilgraf、Andreas Pfaltz

  DOI：10.1002/adsc.200404168

  日期：2005.1

  has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts

  制备了一系列N，P-配体，其包含手性恶唑啉环和嵌入在二氮磷吡啶环中的双（N-磺酰基氨基）膦基或衍生自TADDOL的环状亚磷酸酯基作为第二手性单元。这些模块化配体易于从手性氨基醇和手性1,2-二胺或TADDOLs合成。发现衍生自这些配体的钯和铱配合物分别是对映选择性烯丙基烷基化和烯烃氢化的有效催化剂。
• New Ligands for Regio- and Enantiocontrol in Pd-Catalyzed Allylic Alkylations
  作者：Roger Prétôt、Andreas Pfaltz

  DOI：10.1002/(sici)1521-3773(19980216)37:3<323::aid-anie323>3.0.co;2-t

  日期：1998.2.16

  The branched, chiral products 1 are formed preferentially in the allylic alkylations in Equation (1) when the Pd catalyst contains the P,N ligand L* or derivatives thereof. The ligands are readily synthesized from commercially available precursors.

  当Pd催化剂包含P，N配体L *或其衍生物时，优选在等式（1）的烯丙基烷基化反应中形成支链手性产物1。配体易于从可商购的前体合成。
• Chiral Bis(<i>N</i>-tosylamino)phosphine- and TADDOL-Phosphite-Oxazolines as Ligands in Asymmetric Catalysis
  作者：Robert Hilgraf、Andreas Pfaltz

  DOI：10.1055/s-1999-2939

  日期：1999.11

  A series of P,N-ligands containing a chiral oxazoline ring and a chiral bis(N-tosylamino)phosphine group derived from a 1,2-diamine or a chiral cyclic phosphite group derived from TADDOL has been prepared. These compounds proved to be efficient ligands for enantiocontrol of palladium-catalyzed allylic alkylations and iridium-catalyzed hydrogenations of olefins.

  一系列含手性噁唑啉环和手性双(N-甲苯磺酰氨基)膦基团（源自1,2-二胺）或手性环状亚磷酸酯基团（源自TADDOL）的P,N配体已被合成。这些化合物被证明是钯催化的烯丙基烷基化反应和铱催化的烯烃氢化反应中高效的手性控制配体。
• SimplePHOX, a Readily Available Chiral Ligand System for Iridium-Catalyzed Asymmetric Hydrogenation
  作者：Sebastian P. Smidt、Frederik Menges、Andreas Pfaltz

  DOI：10.1021/ol049235w

  日期：2004.6.1

  [reaction: see text] New Ir-SimplePHOX complexes Ir-6-Ir-9 catalyze the quantitative, highly enantioselective hydrogenation of a range of unfunctionalized and functionalized olefins. Synthesis, catalytic results, and X-ray crystal structures are presented here.

  [反应：见正文]新型Ir-SimplePHOX络合物Ir-6-Ir-9催化了一系列未官能化和官能化烯烃的定量，高对映选择性氢化。本文介绍了合成，催化结果和X射线晶体结构。
• Chiral Bis(<i>N</i>-arylamino)phosphine-oxazolines: Synthesis and Application in Asymmetric Catalysis
  作者：Marc Schönleber、Robert Hilgraf、Andreas Pfaltz

  DOI：10.1002/adsc.200800221

  日期：2008.9.5

  N-alkylation of chiral 1,2-diamines followed by ring closure with phosphorus trichloride (PCl3) and subsequent coupling with an oxazoline alcohol resulted in a new class of N,P ligands. The corresponding iridium tetrakis[3,5-bis(trifluormethyl)phenyl]borate (BArF) complexes were found to be efficient catalysts for the enantioselective hydrogenation of unfunctionalized olefins and α,β-unsaturated carboxylic

  手性1,2-二胺的N-芳基化或N-烷基化，然后用三氯化磷（PCl 3）闭环，然后与恶唑啉醇偶联，产生了新的一类N，P配体。发现相应的四[3,5-双（三氟甲基）苯基]硼酸铱（BAr F）配合物是未官能化烯烃和α，β-不饱和羧酸酯的对映选择性氢化的有效催化剂。