1-ethylidene-2,3-dihydro-1H-indene | 38950-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-ethylidene-2,3-dihydro-1H-indene
• 英文别名: (Z)-1-Ethylideninden；(3Z)-3-ethylidene-1,2-dihydroindene
• CAS: 38950-74-2
• 化学式: C₁₁H₁₂
• 分子量: 144.216
• InChiKey: QGSJWCSXPZNDGU-MBXJOHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  乙基三苯基溴化膦 、 1-茚酮 生成 1-ethylidene-2,3-dihydro-1H-indene 、 1-ethylideneindan
  参考文献：
  名称：

  Interproton allylic spin-spin coupling involving exocyclic groups

  摘要：

  55 个含有外环基团的化合物的 N.m.r. 的 N.m.r 参数。在未受约束的 结构中，横向和顺式烯丙基偶联常数的相对值（以及绝对值 耦合常数的相对值（以及绝对值）取决于二面角的大小。 还发现了其他影响。烯丙基耦合常数的大小 外环亚甲基的质子之间的烯丙基偶联常数以及涉及外环亚乙基和亚异丙基的同烯丙基偶联常数的大小随环的大小而系统地变化。 随环的大小而变化。

  DOI：

  10.1071/ch9721669

文献信息

• Catalytic Ring Expanding Difluorination: An Enantioselective Platform to Access β,β‐Difluorinated Carbocycles
  作者：Louise Ruyet、Christoph Roblick、Joel Häfliger、Zi‐Xuan Wang、Tobias Jürgen Stoffels、Constantin G. Daniliuc、Ryan Gilmour

  DOI：10.1002/anie.202403957

  日期：——

  Cyclic β,β‐difluoro‐carbonyl compounds have a venerable history as drug discovery leads, but limitations in the synthesis arsenal continue to impede chemical space exploration. This challenge is particularly acute in the arena of fluorinated medium rings where installing the difluoromethylene unit subtly alters the ring conformation by expanding the internal angle (∠C−CF₂−C>∠C−CH₂−C): this provides a handle to modulate physicochemistry (e.g. pK_a). To reconcile this disparity, a highly modular ring expansion has been devised that leverages simple α,β‐unsaturated esters and amides, and processes them to one‐carbon homologated rings with concomitant geminal difluorination (6 to 10 membered rings, up to 95 % yield). This process is a rare example of the formal difluorination of an internal alkene and is enabled by sequential I(III)‐enabled O‐activation. Validation of enantioselective catalysis in the generation of unprecedented medium ring scaffolds is reported (up to 93 : 7 e.r.) together with X‐ray structural analyses and product derivatization.
• Interproton allylic spin-spin coupling involving exocyclic groups
  作者：GP Newsoroff、S Sternhell

  DOI：10.1071/ch9721669

  日期：——

  N.m.r. parameters for 55 compounds incorporating exocyclic groups were obtained. In unstrained structures the relative (as well as the absolute) magnitudes of transoid and cisoid allylic coupling constants depend on the magnitudes of the dihedral angles but additional effects were also identified. The magnitudes of geminal coupling constants between the protons of exocyclic methylene groups and of homoallylic coupling constants involving exocyclic ethylidene and isopropylidene groups vary systematically with ring size.

  55 个含有外环基团的化合物的 N.m.r. 的 N.m.r 参数。在未受约束的 结构中，横向和顺式烯丙基偶联常数的相对值（以及绝对值 耦合常数的相对值（以及绝对值）取决于二面角的大小。 还发现了其他影响。烯丙基耦合常数的大小 外环亚甲基的质子之间的烯丙基偶联常数以及涉及外环亚乙基和亚异丙基的同烯丙基偶联常数的大小随环的大小而系统地变化。 随环的大小而变化。