3-chloro-1-phenylpropane-1,2-dione

• 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-chloro-1-phenylpropane-1,2-dione
• 化学式: C₉H₇ClO₂
• 分子量: 182.606
• InChiKey: ILSYIFFCHRKENV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-1-phenylpropane-1,2-dione 、 N-苯基苄脒 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到1-phenyl-2-(2-phenyl-1H-indol-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  铑（III）催化的N-苯基am与α-Cl酮的环化反应直接合成3-环戊二烯

  摘要：

  在本研究中，开发了一种新的合成策略，可通过Rh（III）催化的C–H活化和N-苯基am与α-Cl酮的环合级联反应直接生产通用的3-acylindoles ，其中α-Cl酮用作不寻常的一碳（sp 3）合成子。该策略具有较高的区域选择性，效率，宽的底物耐受性和温和的反应条件，这进一步强调了其在药物分子合成中的合成效用。

  DOI：

  10.1021/acs.orglett.8b03383
• 作为产物：
  描述：

  1-苯基-1,2-丙二酮 在 N,N,N-trimethylbenzenemethanaminium dichloroiodate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 3-chloro-1-phenylpropane-1,2-dione
  参考文献：
  名称：

  铑（III）催化的N-苯基am与α-Cl酮的环化反应直接合成3-环戊二烯

  摘要：

  在本研究中，开发了一种新的合成策略，可通过Rh（III）催化的C–H活化和N-苯基am与α-Cl酮的环合级联反应直接生产通用的3-acylindoles ，其中α-Cl酮用作不寻常的一碳（sp 3）合成子。该策略具有较高的区域选择性，效率，宽的底物耐受性和温和的反应条件，这进一步强调了其在药物分子合成中的合成效用。

  DOI：

  10.1021/acs.orglett.8b03383

文献信息

• Synthesis of α-Functionalized Trichloromethylcarbinols
  作者：Ram N. Ram、Vineet Kumar Soni

  DOI：10.1021/acs.joc.5b01547

  日期：2015.9.4

  A new series of alpha-functionalized trichloromethylcarbinols have been synthesized from corresponding alpha-halomethyl ketones, esters, and amides in 48-78% overall yields. Reactivity of nitrates obtained in the first step was dependent on the electron-withdrawing nature of the functional groups, and increases with increasing electron deficiency. Synthetic applications of such trichloromethylcarbinols for the preparation of chloromethyl-alpha-diketones, trichloromethylated dihydrofurans, and enol acetates of alpha-functionalized acid chlorides have been demonstrated. The reaction of these compounds in the Jocic-Reeve reaction was also demonstrated.
• [EN] METHOD FOR DETECTING AND IDENTIFICATION OF HAZARDOUS SUBSTANCE<br/>[FR] PROCEDE DE DETECTION ET D'IDENTIFICATION D'UNE SUBSTANCE DANGEREUSE
  申请人：DINEFF PETER DONCHEV

  公开号：WO2003095998A1

  公开（公告）日：2003-11-20

  The invention is related to a method for detection and identification of concealed substances or materials that are hazardous to humans and environment. The effecttive use of the method for detection and identification of hazardous substances, concealed by their inclusion in the masking matrix of various dielectric materials, is realized on the basis of the possibility of performing detection and identification of the hazardous substance in the matrix by means of the characteristic thermal picture of the material after thermal activating with a thermal pulse of defined geometrical parameters and energy, as said picture is an integral characteristic of the material ability to absorb the stimulating visible and infrared radiation and to transform it into a bulk or surface source of heat for the remaining part of the material, of the material ability to emit back the absorbed radiation, changing the wavelength of the incident radiation, and also of the material ability to perceive the absorbed thermal energy through thermal conductivity from the shaped-up secondary source of heat and to change its own temperature in that transitional thermal process.
• Direct Synthesis of 3-Acylindoles through Rhodium(III)-Catalyzed Annulation of<i>N</i>-Phenylamidines with α-Cl Ketones
  作者：Jianhui Zhou、Jian Li、Yazhou Li、Chenglin Wu、Guoxue He、Qiaolan Yang、Yu Zhou、Hong Liu

  DOI：10.1021/acs.orglett.8b03383

  日期：2018.12.7

  versatile 3-acylindoles through Rh(III)-catalyzed C–H activation and annulation cascade of N-phenylamidines with α-Cl ketones was developed, in which α-Cl ketones serve as unusual one-carbon (sp3) synthons. This strategy features high regioselectivity, efficiency, wide substrate tolerance, and mild reaction conditions, which further underscore its synthetic utility in drug molecule synthesis.

  在本研究中，开发了一种新的合成策略，可通过Rh（III）催化的C–H活化和N-苯基am与α-Cl酮的环合级联反应直接生产通用的3-acylindoles ，其中α-Cl酮用作不寻常的一碳（sp 3）合成子。该策略具有较高的区域选择性，效率，宽的底物耐受性和温和的反应条件，这进一步强调了其在药物分子合成中的合成效用。