1-乙酰基-1-苯甲酰环丙烷 | 5186-09-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-乙酰基-1-苯甲酰环丙烷
• 英文名称: 1-acetyl-1-benzoyl cyclopropane
• 英文别名: 1-acetyl-1-benzoyl-cyclopropane；1-acetyl-1-benzoylcyclopropane；1-Acetyl-1-benzoyl-cyclopropan；1-Acetyl-1-benzoylcyclopropan；1-(1-benzoylcyclopropyl)ethanone
• CAS: 5186-09-4
• 化学式: C₁₂H₁₂O₂
• mdl: MFCD00459752
• 分子量: 188.226
• InChiKey: CXGABAPZPANLJE-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914399090
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

反应信息

• 作为反应物：
  描述：

  1-乙酰基-1-苯甲酰环丙烷 在 三乙胺 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 312.33h， 生成 [(E)-4-oxo-6-phenylhex-5-enyl] benzoate
  参考文献：
  名称：

  An unexpected Lewis acids-catalyzed tandem ring-opening rearrangement of vinylcyclopropane ketone with aryl aldehyde

  摘要：

  A novel tandem reaction of vinylcyclopropane ketone with benzaldehyde has been successfully developed. This provides a new method for the preparation of gamma-oxo-hexenone derivatives from easily accessible starting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.035
• 作为产物：
  描述：

  (3-benzoyl-4-oxopentyl)mercury(II) chloride 在 氢氧化钾 、 4-羟基戊-3-烯-2-酮 作用下， 以 乙醇 为溶剂， 生成 1-乙酰基-1-苯甲酰环丙烷
  参考文献：
  名称：

  The Reaction of Oxymercurials with Active Methylene Compounds and the Demercuration of the Resulting Mercurials with Acid and Base

  摘要：

  DOI：

  10.1021/jo01340a023

文献信息

• Synthesis of functionalized 2-(arylthio)benzoates by formal [3+3] cyclizations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones and 1,3-diacylcyclopropanes
  作者：Inam Iqbal、Muhammad Imran、Nasir Rasool、Muhammad A. Rashid、Munawar Hussain、Alexander Villinger、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2009.06.119

  日期：2009.9

  Functionalized 2-(arylthio)benzoates are prepared by formal [3+3] cyclizations of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones and 1,1-diacylcyclopropanes.

  通过3-芳基硫基-1-三甲基甲硅烷氧基-1，3-丁二烯与3-甲硅烷氧基-2-烯-1-酮和1，1-二酰基环丙烷的正式[3 + 3]环化反应来制备官能化的2-（芳硫基）苯甲酸酯。
• Organocatalytic Cloke–Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans
  作者：Jingfang Zhang、Yuhai Tang、Wen Wei、Yong Wu、Yang Li、Junjie Zhang、Yuansuo Zheng、Silong Xu

  DOI：10.1021/acs.orglett.7b00805

  日期：2017.6.16

  An organocatalytic Cloke–Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate

  利用均轭共轭加成工艺开发了环丙基酮对2，3-二氢呋喃的有机催化Cloke-Wilson重排。以1,4-二氮杂双环[2.2.2]辛烷为催化剂，在DMSO中于120°C进行的重排通常以高收率，唯一的区域选择性和较宽的底物范围进行。该机构包括立体化学分析和中间隔离支撑一个S的检查Ñ机制的1型环开口。
• [5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-<i>c</i>]pyridines
  作者：Peng Huang、Rui Zhang、Yongjiu Liang、Dewen Dong

  DOI：10.1021/ol302314c

  日期：2012.10.19

  synthesis of 2,3-dihydrofuro[3,2-c]pyridines are described. Ammonium acetate (NH4OAc) is used as an ammonia source in both routes. The first route utilizes 1-acyl-1-[(dimethylamino)alkenoyl]cyclopropanes as a five-carbon 1,5-bielectrophilic species and combines the [5C + 1N] annulation and regioselective ring-enlargement of cyclopropyl ketone into one pot, whereas the second route utilizes 3-acyl-2-[(dim

  描述了两种基于[5C + 1N]环合的新颖路线，用于合成2,3-二氢呋喃[3,2- c ]吡啶。两种途径均使用乙酸铵（NH 4 OAc）作为氨源。第一种方法利用1-酰基-1-[[（二甲基氨基）链烯酰基]环丙烷作为五碳1,5-双亲电子物质，并将环丙基酮的[5C + 1N]环合和区域选择性环扩大结合到一个罐中，而第二种方法利用3-酰基-2-[（（二甲氨基）烯基] -4,5-二氢呋喃作为五碳合成子，其涉及顺序的分子间氮杂加成，分子内氮杂亲核加成/消除和脱水反应。
• Synthesis and characterization of bis-cyclopropanated 1,3,5-tricarbonyl compounds. A combined synthetic, spectroscopic and theoretical study
  作者：Thomas Rahn、Franziska Bendrath、Martin Hein、Wolfgang Baumann、Haijun Jiao、Armin Börner、Alexander Villinger、Peter Langer

  DOI：10.1039/c1ob05455d

  日期：——

  Bis-cyclopropanated 1,3,5-tricarbonyl compounds were prepared by a sequence of Claisen condensations and cyclopropanations. The optimization of the conditions proved to be very important to suppress retro-Claisen reactions. The conformation of these molecules was studied by experimental and computational methods. The syn/syn;syn/syn conformation is present for all derivatives. It is exclusively present in the case of the derivative containing a phenyl group located at the terminal carbon atom. In most cases, equilibria with other conformers are found.

  双环丙烯化的1,3,5-三羰基化合物是通过一系列克莱森缩合反应和环丙烯化反应制备的。优化反应条件被证明对抑制逆克莱森反应非常重要。这些分子的构象通过实验和计算方法进行了研究。所有衍生物均呈现出syn/syn；syn/syn构象。在含有位于末端碳原子的苯基的衍生物中，该构象是独占性的。在大多数情况下，还发现与其他构象体的平衡。
• Efficient and Divergent Synthesis of Functionalized Cyclopropanes via Iodoform Reaction
  作者：Ning Zhang、Dewen Dong、Dingyuan Zhang、Rui Zhang、Dexuan Xiang、Yongjiu Liang

  DOI：10.1055/s-0031-1289693

  日期：2012.3

  Efficient and divergent one-pot synthesis of cyclopropyl amides and esters from readily available 1-acetylcyclopropanes via iodoform reaction based on the selection of reaction conditions is reported. A series of substituted cyclopropyl amides were synthesized from 1-acetylcyclopropanes, iodine, and ammonia in water in the presence of K2CO3 in good yields, whereas substituted cyclopropyl esters were

  据报道，基于反应条件的选择，通过碘仿反应从易得的1-乙酰基环丙烷通过一锅法高效，多样地合成了环丙基酰胺和酯。在K 2 CO 3存在下，由1-乙酰基环丙烷，碘和氨在水中以高收率合成了一系列取代的环丙基酰胺，而由1-乙酰基环丙烷与碘和醇在乙醇中的反应制得了取代的环丙基酯。 DBU的存在。 环丙烷-碘仿反应-碘-酰胺-水