3-isopropylidene-5-phenyl-2(3H)-furanone | 22060-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-isopropylidene-5-phenyl-2(3H)-furanone
• 英文别名: 3-dimethylmethylene-5-phenyl-2-furanone；5-phenyl-3-(propan-2-ylidene)furan-2(3H)-one；2-Isopropyliden-4-phenylbut-3-eno-4-lacton；2-Isopropyliden-4-phenyl-γ-buterolacton；3-isopropylidene-5-phenyl-3H-furan-2-one；5-Phenyl-3-propan-2-ylidenefuran-2-one
• CAS: 22060-64-6
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: DPCWTNVULAKZIO-UHFFFAOYSA-N

物化性质

• 熔点：
  104-108 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  160 °C(Press: 0.02 Torr)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl trans-1-(1-hydroxy-1-methylethyl)-2-phenyl-2-(trimethylsiloxy)cyclopropanecarboxylate 在 盐酸 、 2-甲基苯磺酸 作用下， 生成 3-isopropylidene-5-phenyl-2(3H)-furanone
  参考文献：
  名称：

  Efficient and flexible syntheses of paraconic esters and other highly substituted furanone derivatives from methyl 2-siloxycyclopropanecarboxylates

  摘要：

  DOI：

  10.1021/jo00246a010

文献信息

• Rhodium(<scp>ii</scp>)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans
  作者：Kostiantyn O. Marichev、Yi Wang、Alejandra M. Carranco、Estevan C. Garcia、Zhi-Xiang Yu、Michael P. Doyle

  DOI：10.1039/c8cc05623d

  日期：——

  Donor–acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.

  由Enoldiazoketones形成的供体-受体环丙烯通过一种新的机制进行催化重排，生成5-芳基-2-硅氧基呋喃，该机制涉及将羰基氧亲核加成到铑活化的环丙烯上。
• Synthesis of functionalized furan derivatives by hydroxyalkylation of methyl 2-siloxycyclopropanecarboxylates
  作者：Christiane Brückner、Hans-Ulrich Reissig

  DOI：10.1039/c39850001512

  日期：——

  A variety of methyl tetrahydrofuran-3-carboxylates (4) or the 5-oxo analogues (6) are available in good overall yield by deprotonation of cyclopropanes (1), addition of carbonyl compounds, ring cleavage, and reductive or oxidative work-up, respectively.

  通过环丙烷的去质子化（1），羰基化合物的添加，环的裂解以及还原性或氧化性的处理，可以获得高产率的各种四氢呋喃-3-羧酸甲酯（4）或5-氧代类似物（6）。 ， 分别。
• Chemo- and Regioselective Cyclohydrocarbonylation of α-Keto Alkynes Catalyzed by a Zwitterionic Rhodium Complex and Triphenyl Phosphite
  作者：Bernard G. Van den Hoven、Bassam El Ali、Howard Alper

  DOI：10.1021/jo000230w

  日期：2000.6.1

  alpha-Keto alkynes react with CO and H-2 in the presence of catalytic quantities of the zwitterionic rhodium complex (eta(6)-C6H5BPh3)Rh--(+)(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.
• Catalytic iron-mediated carbon-oxygen and carbon-carbon bond formation in [4 + 1] assembly of alkylidenebutenolides
  作者：Matthew S. Sigman、Charles E. Kerr、Bruce E. Eaton

  DOI：10.1021/ja00069a081

  日期：1993.8
• BRUCKNER, CHRISTIANE;REISSIG, HANS-ULRICH, J. ORG. CHEM., 53,(1988) N 11, 2440-2450
  作者：BRUCKNER, CHRISTIANE、REISSIG, HANS-ULRICH

  DOI：——

  日期：——