4-[(3-氯苯基)亚甲基]-2-甲基-1,3-恶唑-5-酮 | 57689-69-7

• 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
• 中文名称: 4-[(3-氯苯基)亚甲基]-2-甲基-1,3-恶唑-5-酮
• 英文名称: 4-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2-methyl-4H-oxazol-5-one
• 英文别名: 5(4H)-Oxazolone, 4-[(3-chlorophenyl)methylene]-2-methyl-；4-[(3-chlorophenyl)methylidene]-2-methyl-1,3-oxazol-5-one
• CAS: 57689-69-7
• 化学式: C₁₁H₈ClNO₂
• mdl: MFCD26143170
• 分子量: 221.643
• InChiKey: PPAQRXQTAMCHKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(3-氯苯基)亚甲基]-2-甲基-1,3-恶唑-5-酮 在 盐酸 、 乙酰氯 作用下， 生成 methyl 3-(3-chlorophenyl)-2-hydroxyprop-2-enoate
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8
• 作为产物：
  描述：

  3-氯苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 生成 4-[(3-氯苯基)亚甲基]-2-甲基-1,3-恶唑-5-酮
  参考文献：
  名称：

  具有2,2'-叔丁基甲基膦基的Atropos联苯双膦配体，用于铑催化烯醇酯的不对称加氢

  摘要：

  这是我们先前有关Atropos联苯双膦配体开发的工作的更新。单晶X射线衍射证实了Atropos出乎意料的结构性能，该结果与我们先前工作中所述的计算结果相符。这种具有联苯骨架和2,2'-叔丁基甲基膦基的P-stereogenic bisphosphine配体已被用于Rh催化的烯醇酯的不对称加氢反应，尚未得到广泛研究，可用于合成几种重要的生物活性化合物。尽管在对映选择性方面仍有进一步改进的余地，但本文报道的结果提供了对这类配体的进一步理解。

  DOI：

  10.1002/adsc.201800774

文献信息

• Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation
  作者：Lu Zheng、Dan Zheng、Yanru Wang、Chengyuan Yu、Kun Zhang、Hua Jiang

  DOI：10.1039/c9ob01649j

  日期：——

  A series of chiral bisphosphine ligands were designed and synthesized based on single-handed quinoline oligoamide foldamers. The bisphosphine ligands can coordinate with Rh(cod)2BF4 in a 1 : 1 stoichiometry and the resulted chiral Rh(I) catalysts were applied in the asymmetric hydrogenation of α-dehydroamino acid esters, in which excellent conversions and promising levels of enantioselectivity were

  基于单手喹啉寡酰胺折叠剂设计和合成了一系列手性双膦配体。双膦配体可以以1：1的化学计量比与Rh（cod）2 BF 4配位，并将所得的手性Rh（I）催化剂用于α-脱氢氨基酸酯的不对称加氢中，其中出色的转化率和对映选择性水平很有希望实现了。
• Cation-Triggered Switchable Asymmetric Catalysis with Chiral Aza-CrownPhos
  作者：Guang-Hui Ouyang、Yan-Mei He、Yong Li、Jun-Feng Xiang、Qing-Hua Fan

  DOI：10.1002/anie.201411593

  日期：2015.3.27

  AbstractAn aza‐crown ether, modified phosphoramidite ligand, has been designed and synthesized. The ON/OFF reversible switch of catalytic activity for its rhodium catalyst was thoroughly investigated in the asymmetric hydrogenation of dehydroamino acid esters modulated by host–guest interactions. In the OFF state, the catalyst is almost inactive (less than 1 % conversion) because of the formation of an intermolecular sandwich complex by two aza‐crown ether moities and the cationic rhodium metal center. In using alkali‐metal‐cations as the trigger, the catalytic activity was turned ON and consequently resulted in full conversions and excellent enantioselectivities (up to 98 % ee).
• Desai; Bhatt; Shah, Il Farmaco, 1996, vol. 51, # 5, p. 361 - 366
  作者：Desai、Bhatt、Shah、Undavia、Trivedi、Narayanan

  DOI：——

  日期：——
• Upadhyay; Pandya; Parekh, Journal of the Indian Chemical Society, 1991, vol. 68, # 5, p. 296 - 298
  作者：Upadhyay、Pandya、Parekh

  DOI：——

  日期：——
• Upadhyay; Joshi; Baxi, Journal of the Indian Chemical Society, 1991, vol. 68, # 6, p. 364 - 365
  作者：Upadhyay、Joshi、Baxi、Parikh

  DOI：——

  日期：——