4-(2-phenylethyl)-4,5-dihydro-3H-furan-2-one | 111748-85-7

• 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: 4-(2-phenylethyl)-4,5-dihydro-3H-furan-2-one
• 英文别名: 4-(2-phenylethyl)dihydrofuran-2-one；4-(2-Phenylethyl)oxolan-2-one
• CAS: 111748-85-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: DQXHHSPCCIUBPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (4R,6S)-4-Phenethyl-6-trimethylsilanyl-oxepan-2-one 在 palladium dichloride air 、 sodium methylate 、 氢气 、 间氯过氧苯甲酸 、 三氟乙酸 、 copper(l) chloride 作用下， 以 甲醇 为溶剂， 反应 0.02h， 生成 4-(2-phenylethyl)-4,5-dihydro-3H-furan-2-one
  参考文献：
  名称：

  3-Substituted-γ-butyrolactones from 5-Trimethylsilyl-2-cyclohexenone. Synthesis of (−)-Enterolactone

  摘要：

  1,4-Adducts of 5-trimethylsilyl-2-cyclohexenone (1) with Grignard reagents were converted to various hexanoate derivatives and γ-butyrolactones.从光学纯的 1 开始，合成了 (-)- 肠内酯（因子 X）。

  DOI：

  10.1246/cl.1988.805

文献信息

• Cobalt-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Allylic and Benzylic Grignard Reagents and Their Application to Tandem Radical Cyclization/Cross-Coupling Reactions
  作者：Hirohisa Ohmiya、Takashi Tsuji、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1002/chem.200400545

  日期：2004.11.19

  Details of cobalt-catalyzed cross-coupling reactions of alkyl halides with allylic Grignard reagents are disclosed. A combination of cobalt(II) chloride and 1,2-bis(diphenylphosphino)ethane (DPPE) or 1,3-bis(diphenylphosphino)propane (DPPP) is suitable as a precatalyst and allows secondary and tertiary alkyl halides--as well as primary ones--to be employed as coupling partners for allyl Grignard reagents

  公开了烷基卤化物与烯丙基格利雅试剂的钴催化的交叉偶联反应的细节。氯化钴（II）和1,2-双（二苯基膦基）乙烷（DPPE）或1,3-双（二苯基膦基）丙烷（DPPP）的组合适合作为预催化剂，并允许使用仲和叔烷基卤化物作为主要试剂-可用作烯丙基格氏试剂的偶联伙伴。该反应提供了季碳中心的简便合成，而钯，镍和铜催化剂几乎是不可能的。苄基，甲基烯丙基和巴豆基格氏试剂均可以与卤代烷偶联。苄基化肯定需要DPPE或DPPP作为配体。反应机理应包括由母体烷基卤生成烷基。可以根据串联自由基环化/交叉偶联反应来解释该机理。此外，还描述了5-烷氧基-6-卤代-4-氧杂-1-氧杂-1-己烯衍生物的偶发串联自由基环化/环丙烷化/羰基烯丙基化。以碳为中心的自由基的中间体导致母体烷基卤化物的原始立体化学丧失，从而产生了外消旋烷基卤化物不对称交叉偶联的可能性。
• Conjugate addition of lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides: a novel synthesis of functionalized esters and lactones having a tertiary or a quaternary carbon at the β-position
  作者：Tsuyoshi Satoh、Shimpei Sugiyama、Yuhki Kamide、Hiroyuki Ota

  DOI：10.1016/s0040-4020(03)00636-7

  日期：2003.6

  Addition of the lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones or aldehydes, gave esters having a tertiary or a quaternary carbon at the 3-position, and chlorine and sulfinyl groups at the 4-position in high to quantitative yields. The adducts were converted to various esters having methyl, formyl, and hydroxycarbonyl

  的锂酯烯醇化物加成到1-氯乙烯基p -甲苯基亚砜，这是从氯合成p -甲苯基砜和酮或醛，得到具有叔或在3-位置上的季碳，并在氯和亚磺酰基酯高产量到定量产量的4位。加合物被转化为在3-位具有甲基，甲酰基和羟羰基的各种酯。从加合物中以良好的总收率实现了一种新的合成γ-内酯的方法，包括螺型γ-内酯和α-亚甲基γ-内酯。还讨论了该方法的范围和局限性以及反应机理。
• [EN] NOVEL PYRROLE DERIVATIVES AS PHARMACEUTICAL AGENTS<br/>[FR] DERIVES DE PYRROLE UTILISES COMME AGENTS PHARMACEUTIQUES
  申请人：LILLY CO ELI

  公开号：WO2002094833A1

  公开（公告）日：2002-11-28

  Novel pyrrazole derivative compounds and their use as pharmaceutical agents, in particular their use as TGF-beta signal transduction inhibitors. The disclosed invention relates to compounds of the structure (I) wherein (I) is a four, five, or six membered saturated ring and X is C, O or S.

  小说吡唑衍生物化合物及其作为药物制剂的用途，特别是作为TGF-beta信号传导抑制剂的用途。所披露的发明涉及结构为（I）的化合物，其中（I）是四、五或六元饱和环，X为C，O或S。
• Novel pyrrole derivatives as pharmaceutical agents
  申请人：——

  公开号：US20040106604A1

  公开（公告）日：2004-06-03

  Novel pyrrazole derivative compounds and their use as pharmaceutical agents, in particular their use as TGF-beta signal transduction inhibitors. The disclosed invention relates to compounds of the structure (I) wherein (I) is a four, five, or six membered saturated ring and X is C, O or S. 1

  小说吡唑衍生物化合物及其作为药物代理的使用，特别是其作为TGF-beta信号转导抑制剂的使用。所公开的发明涉及结构（I）的化合物，其中（I）是四、五或六个成员的饱和环，X是C、O或S。1
• Pyrrole derivatives as pharmaceutical agents
  申请人：Eli Lilly and Company

  公开号：US07087626B2

  公开（公告）日：2006-08-08

  Novel pyrrazole derivative compounds and their use as pharmaceutical agents, in particular their use as TGF-beta signal transduction inhibitors. The disclosed invention relates to compounds of the structure (I) wherein (I) is a four, five, or six membered saturated ring and X is C, O or S

  小说吡唑衍生物化合物及其作为药物代理的用途，特别是它们作为TGF-beta信号转导抑制剂的用途。所披露的发明涉及结构为(I)的化合物，其中(I)是四、五或六成员饱和环，X是C、O或S。