(S)-2-methyl-4-phenyl-4,5-dihydrooxazole | 222622-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-methyl-4-phenyl-4,5-dihydrooxazole
• 英文别名: (4S)-4,5-dihydro-2-methyl-4-phenyl-1,3-oxazole；(S)-2-methyl-4-phenyl-oxazoline；2-methyl-4-phenyl-4,5-dihydrooxazole；(4S)-2-methyl-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 222622-39-1
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: OADZSDHBFLIAPX-SNVBAGLBSA-N

物化性质

• 沸点：
  250.0±29.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  (S)-2-methyl-4-phenyl-4,5-dihydrooxazole 在 selenium(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  通过聚合的天然化学连接-氧化策略全合成聚双癸酰胺B，C和D

  摘要：

  描述了海洋海绵衍生的环状二肽天然产物Polydiscamides B，C和D的第一批合成。这些分子是通过前所未有的天然化学连接-氧化方案，通过环状和线性片段的融合融合而构建的。

  DOI：

  10.1021/ol502045u
• 作为产物：
  描述：

  2-甲基-4-苯基噁唑 在 [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) 、 (R,R)-(S,S)-PhTRAP 、 氢气 、 四甲基胍 作用下， 以 异丁醇 为溶剂， 80.0 ℃ 、5.07 MPa 条件下， 反应 4.0h， 以91%的产率得到(S)-2-methyl-4-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles

  摘要：

  Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(eta(3)-methallyl)(2)(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.

  DOI：

  10.1021/ja201543h

文献信息

• BENZODIAZEPINE DERIVATIVES, COMPOSITIONS, AND METHODS FOR TREATING COGNITIVE IMPAIRMENT
  申请人：AgeneBio, Inc.

  公开号：US20180170941A1

  公开（公告）日：2018-06-21

  This invention relates to benzodiazepine derivatives, compositions comprising therapeutically effective amounts of those benzodiazepine derivatives and methods of using those derivatives or compositions in treating cognitive impairment associated with central nervous system (CNS) disorders. In particular, it relates to the use of a α5-containing GABA A receptor agonist (e.g., a α5-containing GABA A receptor positive allosteric modulator) as described herein in treating cognitive impairment associated with central nervous system (CNS) disorders in a subject in need or at risk thereof, including, without limitation, subjects having or at risk for age-related cognitive impairment, Mild Cognitive Impairment (MCI), amnestic MCI (aMCI), Age-Associated Memory Impairment (AAMI), Age Related Cognitive Decline (ARCD), dementia, Alzheimer's Disease(AD), prodromal AD, post traumatic stress disorder (PTSD), schizophrenia, bipolar disorder, amyotrophic lateral sclerosis (ALS), cancer-therapy-related cognitive impairment, mental retardation, Parkinson's disease (PD), autism spectrum disorders, fragile X disorder, Rett syndrome, compulsive behavior, and substance addiction. It also relates to the use of a α5-containing GABA A receptor agonist (e.g., a α5-containing GABA A receptor positive allosteric modulator) as described herein in treating brain cancers (including brain tumors, e.g., medulloblastomas), and cognitive impairment associated therewith.

  这项发明涉及苯二氮卓啉衍生物，包括含有这些苯二氮卓啉衍生物的治疗有效量的组合物，以及使用这些衍生物或组合物治疗与中枢神经系统（CNS）疾病相关的认知障碍的方法。具体而言，它涉及在需要或有风险的受试者中治疗与中枢神经系统（CNS）疾病相关的认知障碍，包括但不限于患有或有风险患有与年龄相关的认知障碍、轻度认知障碍（MCI）、遗忘性MCI（aMCI）、年龄相关记忆障碍（AAMI）、年龄相关认知衰退（ARCD）、痴呆症、阿尔茨海默病（AD）、前驱期AD、创伤后应激障碍（PTSD）、精神分裂症、躁郁症、肌萎缩侧索硬化（ALS）、癌症治疗相关认知障碍、智力障碍、帕金森病（PD）、自闭症谱系障碍、脆性X综合症、瑞特综合症、强迫行为和物质成瘾。它还涉及在治疗与之相关的脑癌（包括脑肿瘤，例如髓母细胞瘤）和认知障碍的情况下，如本文所述使用α5含有的GABAA受体激动剂（例如，α5含有的GABAA受体正向变构调节剂）。
• Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand
  作者：Hao Wang、Zibo Bai、Tangqian Jiao、Zhiqiang Deng、Huarong Tong、Gang He、Qian Peng、Gong Chen

  DOI：10.1021/jacs.8b00641

  日期：2018.3.14

  developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.

  使用手性单齿恶唑啉 (MOXin) 配体开发了 Pd 催化的酰胺导向的对映选择性烃功能化未活化烯烃与 CH 亲核试剂。各种吲哚在 C3 位与氨基喹啉偶联的 3-链烯酰胺反应，以良好的收率和对映选择性得到 γ 加成产物。这项研究代表了手性单齿恶唑啉配体开发的重要进展，该配体在不对称催化方面的探索尚未充分。
• Asymmetric Amidoselenenylation of Alkenes Promoted by Camphorselenenyl Sulfate: A Useful Synthetic Route to Enantiopure Oxazolines
  作者：Marcello Tiecco、Lorenzo Testaferri、Claudio Santi、Cristina Tomassini、Francesca Marini、Luana Bagnoli、Andrea Temperini

  DOI：10.1002/1099-0690(200010)2000:20<3451::aid-ejoc3451>3.0.co;2-q

  日期：2000.10

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• Lewis Acid-Catalyzed Asymmetric Diels&amp;ndash;Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives
  作者：Kazuhiro Watanabe、Takashi Hirasawa、Kunio Hiroi

  DOI：10.1248/cpb.50.372

  日期：——

  New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels-Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels-Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.

  已开发出新的手性亚砜-1,3-恶唑啉配体作为路易斯酸催化的不对称Diels-Alder反应的手性配体。在铜（II）催化的不对称Diels-Alder反应中使用手性亚磺酰基1,3-恶唑啉配体可提供内环加合物作为主要产物，具有中等对映选择性。提出了不对称感应机理的基本原理。
• Quest for Efficient Catalysts based on Zinc<i>tert</i>-Butyl Peroxides for Asymmetric Epoxidation of Enones:<i>C₂</i>-<i>vs C₁</i>-Symmetric Auxiliaries
  作者：Abdul Raheem Keeri、Iwona Justyniak、Janusz Jurczak、Janusz Lewiński

  DOI：10.1002/adsc.201500764

  日期：2016.3.17

  Zinc tert‐butyl peroxide‐based catalysts for the asymmetric epoxidation of enones using tert‐butyl hydroperoxide as an oxidant have been developed. A comparative study of chiral monoanioninc N,N′‐bidentate ligands, C2‐symmetric bisoxazolinates and C1‐symmetric enaminooxazolinates, revealed excellent performance of C1‐symmetric auxiliary ligands on catalytic asymmetric epoxidation of enones (up to 96%

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