3-methyl-4-phenylcyclopent-2-en-1-one | 69879-40-9

• 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: 3-methyl-4-phenylcyclopent-2-en-1-one
• CAS: 69879-40-9
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: BHQXSQLAFYLWEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-4-phenylcyclopent-2-en-1-one 在 叠氮基三甲基硅烷 、 碳酸氢钠 、 (S)-CBS 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 28.17h， 生成
  参考文献：
  名称：

  [EN] NIMBOLIDE ANALOGS AND METHODS OF USE THEREOF
  [FR] ANALOGUES DE NIMBOLIDE ET LEURS MÉTHODES D'UTILISATION

  摘要：

  Disclosed herein are compounds of the formula (I) or (II) wherein the variables are defined herein. Also provided are methods of manufacturing and pharmaceutical compositions thereof. In some aspects, the compounds and compositions provided herein may be used as PARP1 inhibitors. In some aspects, the present disclosure provides methods wherein the compounds and compositions described herein are used for the treatment of diseases and disorders, such as cancer.

  公开号：

  WO2022150667A1
• 作为产物：
  描述：

  2-methyl-1-phenylpent-1-en-4-yn-3-yl acetate 在 (PhO)3PAuCl 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 3-methyl-4-phenylcyclopent-2-en-1-one
  参考文献：
  名称：

  Gold(I)-Catalyzed 1,3-Carbofunctionalizations of Anthranils with Vinyl Propargyl Esters To Yield 1,3-Dihydrobenzo[c]-isoxazoles

  摘要：

  This work describes gold-catalyzed 1,3-carbofunctionalizations of anthranils with vinyl propargyl esters to form 1,3-dihydrobenzo[c]-isoxazoles. Excellent diastereoselectivity has been achieved to yield products containing three stereogenic carbons. These new catalytic reactions are operable with anthranils and vinyl propargyl esters over a wide scope, further manifesting the synthetic utility.

  DOI：

  10.1021/acs.orglett.9b00880

文献信息

• A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin
  作者：Brian Brown、Louis S. Hegedus

  DOI：10.1021/jo9919759

  日期：2000.3.1

  A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.

  使用Me3S（O）I，NaH和Sc（OTf）3开发了一种新颖的一锅扩环程序。简要审查了范围和局限性，并提出了一种尝试性机制。将该方法应用于已知的环丁酮1可提供相应的环戊酮，该环戊酮已成功应用于（+）-carbovir和（+）-aristeromycin。
• Diastereodivergent α-Homoallylation of Cyclic Enones
  作者：Po-Chou Chen、Pei-Yun You、Li-Yun Wu、Zhanyi Chin、Kuan-Hua Chiu、Song-Ting Hsieh、Yu-Wen Huang

  DOI：10.1021/acs.orglett.3c04151

  日期：2024.1.19

  diastereoselective [3,3]-sigmatropic rearrangement. Mechanistic investigations revealed that the [3,3]-sigmatropic rearrangement proceeds with transfer of chirality. These inspire a photocatalyzed olefin isomerization of the aldol condensation product leading to a highly diastereoselective [3,3]-sigmatropic rearrangement to furnish the α-homoallylation of cyclic enones. Importantly, this photocatalyzed

  α,β-不饱和羰基是疾病相关蛋白质亲核体的重要结构基序。 α 位立体选择性官能化的方法包括 Morita-Baylis-Hillman、Negishi、Sonogashira、Stille 和 Rauhut-Currier 反应。这里描述的是一种通过一系列共轭加成、羟醛缩合和非对映选择性[3,3]-σ重排对环烯酮进行非对映发散α-同烯丙基化的方法。机理研究表明，[3,3]-σ重排随着手性转移而进行。这些激发了羟醛缩合产物的光催化烯烃异构化，导致高度非对映选择性的[3,3]-σ重排，以提供环烯酮的α-同烯丙基化。重要的是，这种光催化烯烃异构化/非对映选择性[3,3]-σ重排反应序列允许以烯丙基作为合成功能手柄的外型-β-位置的完全立体控制。
• Rhodium(I)-Catalyzed Successive Double Cleavage of Carbon−Carbon Bonds of Strained Spiro Cyclobutanones
  作者：Masahiro Murakami、Kunio Takahashi、Hideki Amii、Yoshihiko Ito

  DOI：10.1021/ja971949x

  日期：1997.10.1
• Gold(I)-Catalyzed 1,3-Carbofunctionalizations of Anthranils with Vinyl Propargyl Esters To Yield 1,3-Dihydrobenzo[<i>c</i>]-isoxazoles
  作者：Manisha Skaria、Pankaj Sharma、Rai-Shung Liu

  DOI：10.1021/acs.orglett.9b00880

  日期：2019.4.19

  This work describes gold-catalyzed 1,3-carbofunctionalizations of anthranils with vinyl propargyl esters to form 1,3-dihydrobenzo[c]-isoxazoles. Excellent diastereoselectivity has been achieved to yield products containing three stereogenic carbons. These new catalytic reactions are operable with anthranils and vinyl propargyl esters over a wide scope, further manifesting the synthetic utility.
• [EN] NIMBOLIDE ANALOGS AND METHODS OF USE THEREOF<br/>[FR] ANALOGUES DE NIMBOLIDE ET LEURS MÉTHODES D'UTILISATION
  申请人：[en]THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM

  公开号：WO2022150667A1

  公开（公告）日：2022-07-14

  Disclosed herein are compounds of the formula (I) or (II) wherein the variables are defined herein. Also provided are methods of manufacturing and pharmaceutical compositions thereof. In some aspects, the compounds and compositions provided herein may be used as PARP1 inhibitors. In some aspects, the present disclosure provides methods wherein the compounds and compositions described herein are used for the treatment of diseases and disorders, such as cancer.