3-[hydroxy(phenyl)methyl]-tetrahydrofuran-2-one | 21690-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-[hydroxy(phenyl)methyl]-tetrahydrofuran-2-one
• 英文别名: 3-(hydroxy-phenyl-methyl)-dihydro-furan-2-one；3-[hydroxy(phenyl)methyl]oxolan-2-one
• CAS: 21690-27-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: PJQAKVWUKSPVKW-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C
• 沸点：
  392.5±15.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[hydroxy(phenyl)methyl]-tetrahydrofuran-2-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以65 %的产率得到α-benzoyl-γ-butyrolactone
  参考文献：
  名称：

  含芳基的饱和γ-丁内酯类化合物及其制备方法和在抗植物病毒方面的应用

  摘要：

  本发明公开了一种含芳基的饱和γ‑丁内酯类化合物及其制备方法和在抗植物病毒方面的应用，化合物的化学结构通式中的R1为连接碳链上取代氢原子的羟基或氧原子；R2为氢或C1–C6的烷基；R3为氢或乙烯基；R4为不同位置取代的氢、甲氧基、甲基、三氟甲基、氟、氯、溴、硝基、C1–C6的烷氧基、取代苄氧基，或其多取代组合，且R4可与苯环可形成含氧杂环；提供了含芳基的饱和γ‑丁内酯类化合物I的新用途，通过半叶枯斑法测定化合物对烟草花叶病毒(TMV)的抑制率，结果表明该类化合物具有优异的抗植物病毒活性，在100～500μg/mL施药量的情况下，对烟草花叶病毒呈现显著的钝化活性、治疗活性和保护活性。

  公开号：

  CN116789620A
• 作为产物：
  描述：

  二氢-3-碘呋喃-2(3H)-酮 、 苯甲醛 在 锰 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以99%的产率得到3-[hydroxy(phenyl)methyl]-tetrahydrofuran-2-one
  参考文献：
  名称：

  从有机卤化物与活化锰制备有机锰试剂

  摘要：

  用镁金属还原Li 2 MnCl 4提供了活化的锰，为在THF中的黑色悬浮液。用活化的锰处理有机卤化物，例如烯丙基溴，α-卤代酯或芳基卤化物，提供了各种有机锰试剂，这些试剂进一步与亲电子试剂反应，得到相应的加合物。带有碘代芳基部分的酮与该活性锰的反应引起环化，从而提供二氢茚衍生物。

  DOI：

  10.1016/s0040-4020(01)00864-x

文献信息

• Smoking compositions containing a flavorant-release additive
  申请人：Philip Morris Incorporated

  公开号：US04690157A1

  公开（公告）日：1987-09-01

  This invention provides smoking compositions which contain a novel hydroxylactone flavorant-release additive. Under cigarette smoking conditions, an additive such as 2-(1-hydroxy-1-phenylmethyl)-.gamma.-butyrolactone pyrolyzes into volatile benzaldehyde and .gamma.-butyrolactone constituents which enhance the flavor and aroma of the cigarette smoke.

  本发明提供了含有新型羟基内酯香味释放添加剂的吸烟组合物。在香烟吸烟条件下，例如2-(1-羟基-1-苯甲基)-γ-丁内酯会分解成挥发性苯甲醛和γ-丁内酯成分，从而增强香烟烟雾的味道和香气。
• Stereocontrolled aldol reactions of butyrolactone: erythro- selectivity via high coordination zinc complexes
  作者：D.A. Widdowson、G.H. Wiebecke、D.J. Williams

  DOI：10.1016/s0040-4039(00)88726-2

  日期：1982.1

  The stereoselection of the lithium catalysed aldol reaction of benzaldehyde and γ-butyrolactone is reversed by zinc ions. The intermediacy of octahedral or square pyramidal zinc complexes is invoked to explain these observations.

  锌离子逆转苯甲醛和γ-丁内酯在锂催化的羟醛反应中的立体选择。八面体或方形金字塔形锌配合物的中间物被用来解释这些观察结果。
• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.
• Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate
  作者：Chien-Tien Chen、Jen-Huang Kuo、Chun-Hsin Li、N. B. Barhate、Sang-Wen Hon、Tai-Wei Li、Shi-Deh Chao、Chia-Cheng Liu、Ying-Chieh Li、I-Hsin Chang、Jin-Sheng Lin、Chin-Jing Liu、Y-Chen Chou

  DOI：10.1021/ol016684c

  日期：2001.11.1

  [GRAPHICS]Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
• A cobalt-phosphine complex as mediator in the formation of carbon-carbon bonds
  作者：Fulvia Orsini、Francesca Pelizzoni、Maurizio Pulici、Lidia M. Vallarino

  DOI：10.1021/jo00080a001

  日期：1994.1