3-isopropyl-1-methyl-1H-indene | 941-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-isopropyl-1-methyl-1H-indene
• 英文别名: 1-methyl-3-propan-2-yl-1H-indene
• CAS: 941-97-9
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: QKSMGVKHQVYHCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-isopropyl-1-methyl-1H-indene 在 臭氧 、 三苯基膦 作用下， 生成 2-(2-Isobutyryl-phenyl)-propionaldehyde
  参考文献：
  名称：

  Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation

  摘要：

  Ozonolyses of 3-methyl- and 3-isopropyl-1-methylindenes (1a,b) in ether gave mainly the corresponding oligomers 3a,b, while in the case of 3-phenyl- and 3-tert-butyl-1-methylindenes (1c,d), the corresponding exo-endo mixtures of ozonides 2c,d were obtained in good yield, the exo isomer being the major one. The ozonolyses of two stereoisomeric keto vinyl ethers, (E)-16 and (Z)-16, demonstrated that the stereochemistry of the derived carbonyl oxide 5c exerts a remarkable influence on the course of the reaction. Particularly interesting is the fact that syn-5c having a proper geometry for the concerted cycloaddition provided ozonide 2c in high yield even in the presence of trifluoroacetophenone. The high degree of similarity in the nature and distribution of the products from the ozonolyses of keto olefin (E)-16 and 1-methyl-3-phenylindene (1c) would be consistent with their respective reactions proceeding predominantly through a common carbonyl oxide intermediate syn-5c.

  DOI：

  10.1021/jo980542n
• 作为产物：
  描述：

  异丁酰苯 在 磷酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 3-isopropyl-1-methyl-1H-indene
  参考文献：
  名称：

  Stereochemistry of Carbenic 1,2-Vinyl Shifts

  摘要：

  Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R'CH=CHC(Ph)=CR2, were found to predominate over gamma-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R' = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R' = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point, to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).

  DOI：

  10.1021/jo971691t

文献信息

• A Gold(I)-Catalyzed Domino Coupling of Alcohols with Allenes Enables the Synthesis of Highly Substituted Indenes
  作者：Alexander Preinfalk、Antonio Misale、Nuno Maulide

  DOI：10.1002/chem.201603154

  日期：2016.10.4

  The reaction of aryl‐substituted allenes with alcohols under gold catalysis led to highly substituted indenes in good yields, with low catalyst loading and under mild conditions. During this domino transformation, two C−C bonds are formed with water as the only byproduct.

  在金催化下，芳基取代的烯与醇的反应导致高取代度的茚满，收率高，催化剂用量低，且条件温和。在此多米诺骨牌转化过程中，两个CC键与水形成了唯一的副产物。
• Asymmetric [3 + 2] annulations catalyzed by a planar-chiral derivative of DMAP
  作者：Erhard Bappert、Peter Müller、Gregory C. Fu

  DOI：10.1039/b603172b

  日期：——

  A planar-chiral DMAP derivative catalyzes an intriguing [3 + 2] annulation reaction of silylated indenes to produce diquinanes that bear three contiguous stereocenters (one quaternary and two tertiary).

  一种平面手性DMAP衍生物催化了一种引人注目的[3 + 2]环化反应，将硅化的茚类化合物转化为具有三个相邻立体中心（二级和三级各两个的一个四级） 的二萘烷。
• Meurling,L., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. 28, p. 295 - 300
  作者：Meurling,L.

  DOI：——

  日期：——
• Stereochemistry of Carbenic 1,2-Vinyl Shifts
  作者：Wolfgang Kirmse、Siegfried Kopannia

  DOI：10.1021/jo971691t

  日期：1998.2.1

  Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R'CH=CHC(Ph)=CR2, were found to predominate over gamma-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R' = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R' = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point, to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).
• Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation
  作者：Shin-ichi Kawamura、Rika Takeuchi、Araki Masuyama、Masatomo Nojima、Kevin J. McCullough

  DOI：10.1021/jo980542n

  日期：1998.8.1

  Ozonolyses of 3-methyl- and 3-isopropyl-1-methylindenes (1a,b) in ether gave mainly the corresponding oligomers 3a,b, while in the case of 3-phenyl- and 3-tert-butyl-1-methylindenes (1c,d), the corresponding exo-endo mixtures of ozonides 2c,d were obtained in good yield, the exo isomer being the major one. The ozonolyses of two stereoisomeric keto vinyl ethers, (E)-16 and (Z)-16, demonstrated that the stereochemistry of the derived carbonyl oxide 5c exerts a remarkable influence on the course of the reaction. Particularly interesting is the fact that syn-5c having a proper geometry for the concerted cycloaddition provided ozonide 2c in high yield even in the presence of trifluoroacetophenone. The high degree of similarity in the nature and distribution of the products from the ozonolyses of keto olefin (E)-16 and 1-methyl-3-phenylindene (1c) would be consistent with their respective reactions proceeding predominantly through a common carbonyl oxide intermediate syn-5c.