3,3-diphenyl-2-propenyl 3-oxobutanoate | 508194-52-3

• 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: 3,3-diphenyl-2-propenyl 3-oxobutanoate
• 英文别名: 3,3-diphenylprop-2-enyl 3-oxobutanoate
• CAS: 508194-52-3
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: IPXCTIIDQBDTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  3,3-diphenyl-2-propenyl 3-oxobutanoate 在 N-甲基咪唑 、 sodium hydroxide 、 salcomine 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 30.0h， 生成 6,6-diphenyl-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: structural tuning of salen ligand

  摘要：

  Intramolecular cyclopropanation of alkenyl alpha-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(11)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl alpha-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(11)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(11)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00167-8
• 作为产物：
  描述：

  双乙烯酮 、 3,3-diphenylprop-2-en-1-ol 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3,3-diphenyl-2-propenyl 3-oxobutanoate
  参考文献：
  名称：

  Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: structural tuning of salen ligand

  摘要：

  Intramolecular cyclopropanation of alkenyl alpha-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(11)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl alpha-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(11)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(11)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00167-8

文献信息

• Manganese(III)-Assisted Specific Intramolecular Addition
  作者：Hiroshi Nishino、Yosuke Ito、Shunsuke Jogo、Noriko Fukuda、Ryo Okumura

  DOI：10.1055/s-0030-1259977

  日期：2011.5

  3-oxobutanamides underwent manganese(III)-mediated oxidative intramolecular addition to produce dihydrofuran-fused macrolides and macrocyclic amides from 8 to 26 members. A similar reaction of the oligooxamethylene-tethered ω-alkenyl 3-oxobutanoates also gave dihydrofuran-fused crown ether type macrolides which had a phase-transfer ability with sodium and potassium picrates. The manganese(III)-assisted specific

  对低聚亚甲基系的ω-烯基3-氧代丁酸酯和3-氧代丁酰胺进行了锰（III）介导的氧化分子内加成反应，制得了8至26个成员的二氢呋喃稠合大环内酯和大环酰胺。低聚氧杂亚甲基系链的ω-烯基3-氧代丁酸酯的类似反应也得到了二氢呋喃稠合的冠醚型大环内酯，其与苦味酸钠和钾具有相转移能力。锰（III）辅助的特定分子内加成反应可以通过ω-烯基部分与锰（III）烯醇化物的π络合来解释。 分子内加成-大环化-氧化-自由基-冠醚
• Synthesis of Bicyclo[3.1.0]hexan-2-ones by Manganese(III) Oxidation in Ethanol
  作者：Hiroshi Nishino、Kentaro Asahi

  DOI：10.1055/s-0028-1083324

  日期：——

  underwent the manganese(III)-induced oxidative intramolecular cyclization in ethanol to produce 3-azabicyclo[3.1.0]hexan-2-ones in good yields. A similar reaction of propenyl 3-oxobutanoates and S-propenyl 3-oxobutanethioates also gave the corresponding 3-oxa- and 3-thiabicy­clo[3.1.0]hexan-2-ones. The reaction details, the structure determination, and the reaction pathway are described. cyclizations - oxidations

  N-丙烯基-3-氧代丁酰胺在乙醇中进行锰（III）诱导的氧化性分子内环化反应，以高收率产生3-氮杂双环[3.1.0]己-2-烯。丙烯基3-氧代丁酸酯和S-丙烯基3-氧代丁烷硫酸酯的类似反应也得到相应的3-氧杂-和3-硫代二环[3.1.0]己-2-基。描述了反应细节，结构确定和反应途径。 环化-氧化-自由基反应-双环[3.1.0]己酮-乙酸锰（III）
• Manganese(III)-based intramolecular macrocyclization of 3,3-diphenyl-2-propenyloxyoligomethylene 3-oxobutanoates
  作者：Shunsuke Jogo、Hiroshi Nishino、Mikio Yasutake、Teruo Shinmyozu

  DOI：10.1016/s0040-4039(02)02282-7

  日期：2002.12

  The reaction of 3,3-diphenyl-2-propenyloxytetramethylene 3-oxobutanoate (14) with manganese(ill) acetate dihydrate in boiling acetic acid caused the oxidative intramolecular radical cyclization to produce 13-methyl-11,11-diphenyl-3,8,12-trioxabicyclo[8.3.0]tridec-13-en-2-one (2(4)) in 94% yield. A similar oxidation of the 3,3-diphenyl-2-propenyloxyoligomethylene 3-oxobutanoates (1(n): n = 2, 3, 6, 8) gave the corresponding macrolides 2(n) (n = 2, 3, 6, 8) in moderate to good yields. A 17-membered crown ether-type macrolide 2, was also obtained in 80% yield by the intramolacular radical cyclization of the oxaethylene-tethered 3-oxobutanoate (11). The structure of the macrolides 2,, (n = 2, 3, 4, 6, 11) has been corroborated by an X-ray crystal structure analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.