Methyl 3-oxo-5-phenylpent-4-enoate | 51081-29-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Methyl 3-oxo-5-phenylpent-4-enoate
• CAS: 51081-29-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: FCRJJPWNWLNCPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-oxo-5-phenylpent-4-enoate 在 camphor-10-sulfonic acid 、 乙二醇 、 lithium aluminium tetrahydride 、 silica gel 作用下， 以 乙醚 为溶剂， 以60%的产率得到5-Hydroxy-1-phenylpent-1-en-3-one
  参考文献：
  名称：

  Direct Conversion of β-Hydroxyketones to Cyclic Disiloxanes

  摘要：

  beta-Hydroxyketones can be directly converted to cyclic disiloxanes using diphenylchlorosilane in the presence of imidazole and an amine base. The reaction is proposed to proceed via a nucleophilic activation mechanism through a cyclic chairlike transition state affording hydrosilylated products with high diastereoselectivity.

  DOI：

  10.1021/ol1024635

文献信息

• 인돌로파이란 유도체 및 이의 합성 방법
  申请人：UNIST(ULSAN NATIONAL INSTITUTE OF SCIENCE AND TECHNOLOGY) 울산과학기술원(120150812047) Corp. No ▼ 230171-0011595BRN ▼620-82-06236

  公开号：KR20210065516A

  公开（公告）日：2021-06-04

  본 발명은 하기 화학식 1로 표시된 신규 인돌로파이란 유도체, 이의 합성 방법 및 이를 유효 성분으로 포함하는 약학적 조성물에 관한 것이다: <화학식 1> 상기 화학식 1 중, R1 내지 R6 및 a2에 대한 설명은 명세서에 기재된 바를 참조한다.

  本发明涉及如下式1所代表的新型吲哚吡喃衍生物、合成它们的方法以及包含它们作为活性成分的药物组合物：<方案 1> 在所述方案 1 中，R1 至 R6 和 a2 的描述参见说明书。
• Bis(imidazolidine)pyridine‐CoCl ₂ : A Novel, Catalytically Active Neutral Complex for Asymmetric Michael Reaction of 1,3‐Carbonyl Compounds with Nitroalkenes
  作者：Takayoshi Arai、Yuko Iimori、Mayu Shirasugi、Ryota Shinohara、Yuri Takagi、Takumi Suzuki、Junma Ma、Satoru Kuwano、Hyuma Masu

  DOI：10.1002/adsc.201900421

  日期：2019.8.21

  A neutral bis(imidazolidine)pyridine (PyBidine)‐CoCl2 complex showed catalytic activity for the Michael reaction of malonates with nitroalkenes. The results indicated that a weak amine base aided enolate formation from the neutral complex, in which the N−H proton of the imidazolidine ligand played a significant role.

  中性双（咪唑烷）吡啶（PyBidine）-CoCl 2络合物显示出对丙二酸酯与硝基烯烃的迈克尔反应的催化活性。结果表明，弱胺碱有助于中性配合物形成烯醇化物，其中咪唑烷配体的NH质子起着重要作用。
• General, Robust, and Stereocomplementary Preparation of β-Ketoester Enol Tosylates as Cross-Coupling Partners Utilizing TsCl−<i>N</i>-Methylimidazole Agents
  作者：Hidefumi Nakatsuji、Kanako Ueno、Tomonori Misaki、Yoo Tanabe

  DOI：10.1021/ol800480d

  日期：2008.6.5

  (Z)-stereocomplementary enol tosylation of beta-ketoesters using TsCl- N-methylimidazole (NMI)-Et3N or LiOH. TsCl coupled with NMI formed a highly reactive N-sulfonylammonium intermediate. Stereocongested secondary alcohols were smoothly sulfonylated using Ts(Ms)Cl-NMI-Et3N. beta-Ketoesters underwent (E)-selective tosylation using TsCl-NMI-Et3N and (Z)-selective tosylation using TsCl-NMI-LiOH (total

  我们已经开发了使用TsCl-N-甲基咪唑（NMI）-Et3N或LiOH进行β-酮酸酯的（E）-或（Z）-立体互补烯醇甲苯磺酸酯化的通用，可靠且经济高效的方法。TsCl与NMI偶联形成高反应性的N-磺酰胺基中间体。使用Ts（Ms）Cl-NMI-Et3N将立体拥挤的仲醇顺利磺酰化。β-酮酸酯使用TsCl-NMI-Et3N进行（E）选择性甲苯磺酰化，使用TsCl-NMI-LiOH进行（Z）选择性甲苯磺酰化（共23个实例；收率60％-99％）。使用烯醇甲苯磺酸盐的立体定向Negishi和Sonogashira偶联成功进行，得到了三取代的α，β-不饱和酯。
• Catalytic asymmetric synthesis of chiral phenols in ethanol with recyclable rhodium catalyst
  作者：Jian Yao、Na Liu、Long Yin、Junhao Xing、Tao Lu、Xiaowei Dou

  DOI：10.1039/c9gc02420d

  日期：——

  A general method to access diverse chiral phenols by rhodium-catalyzed asymmetric conjugate arylation using hydroxylated arylboronic acids in ethanol was developed. Recycling of the rhodium catalyst by flash chromatography on silica gel was feasible in this system. The synthetic utility of the strategy was demonstrated by efficient synthesis of chiral drug tolterodine.

  建立了在乙醇中使用羟基化的芳基硼酸通过铑催化的不对称共轭芳基化反应获得各种手性酚的通用方法。在该系统中通过快速色谱法在硅胶上回收铑催化剂是可行的。通过手性药物托特罗定的有效合成证明了该策略的合成效用。
• Catalytic Asymmetric Conjugate Arylation of γ,δ-Unsaturated β-Dicarbonyl Compounds
  作者：Jian Yao、Long Yin、Yue Shen、Tao Lu、Tamio Hayashi、Xiaowei Dou

  DOI：10.1021/acs.orglett.8b03021

  日期：2018.11.2

  asymmetric conjugate addition to γ,δ-unsaturated β-dicarbonyl compounds was developed. With a chiral diene–rhodium(I) μ-chloro dimer as the catalyst in toluene/H2O, asymmetric conjugate arylation of γ,δ-unsaturated β-dicarbonyl compounds with arylboronic acids proceeded in high efficiency with excellent enantioselectivities. The generated β-dicarbonyl products are versatile chiral synthons, which can

  研发了向γ，δ-不饱和β-二羰基化合物中的第一个催化不对称共轭加成物。用手性二烯-铑（I）μ-氯二聚体作为甲苯/ H 2 O的催化剂，γ，δ-不饱和β-二羰基化合物与芳基硼酸的不对称共轭芳基化反应高效进行，具有出色的对映选择性。生成的β-二羰基产物是通用的手性合成子，可以容易地转化为多种重要的手性结构。