2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropionaldehyde | 139222-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropionaldehyde
• 英文别名: 2-(3-methyl-2-cyclopentenyl)isobutyraldehyde；rac-2-methyl-2-(3-methylcyclopent-2-en-1-yl)propanal；2-methyl-2-(3-methylcyclopent-2-en-1-yl)propanal
• CAS: 139222-34-7
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: SVDLNNVLBMXPTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropionaldehyde 、 正丁醛 在 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以19%的产率得到1,3,3-trimethyl-5-propyl-2,6-dioxabicyclo[2.2.2]octane
  参考文献：
  名称：

  催化不对称Prins双环化的2,6-二氧杂双环[2.2.2]辛烷的内选择性形成

  摘要：

  公开了一种新的路易斯酸催化的内含选择性的γ，δ-不饱和醛或酮的内环选择性Prins双环化成二氧杂双环[2.2.2]辛烷。当使用手性BINOL衍生的N-三flylphosphoramide（NTPA）作为催化剂和乙醛酸酯作为底物时，交叉二聚可提供具有出色的非对映异构和对映选择性的官能化双环缩醛。

  DOI：

  10.1002/chem.201600847
• 作为产物：
  描述：

  α-<3-Methyl-cyclopenten-(3)-yl-1>-isobuttersaeure-nitril, α-Fencholensaeure-nitril 生成 2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropionaldehyde
  参考文献：
  名称：

  EHRMAN M. B.; VOLKOVA O. O.; CHERKAEV G. V.; PRIBYTKOVA I. M.; ANTIPIN M.+, ZH. ORGAN. XIMII, 22,(1986) N 12, 2508-2519

  摘要：

  DOI：

文献信息

• Changes of Lemon Flavor Components in an Aqueous Solution during UV Irradiation
  作者：Yuko Iwanami、Hideki Tateba、Nobuko Kodama、Katsumi Kishino

  DOI：10.1021/jf960100h

  日期：1997.2.1

  A lemon flavor composed of lemon oil, water (pH 6 phosphate buffer), and ethanol, and the lemon-flavored drink were irradiated with UV light. Citral (1 and 2), which is one of the most important components expressing the typical lemon-like odor, significantly decreased with Z-E isomerization and there appeared 2-(3-methyl-2-cyclopenten-1-yl)-2-methyl (6), trans-1,3,3-trimethylbicyclo[3.1.0]hexane-1-carboxaldehyde (7), cis-1,3,3-trimethylbicyclo[3.1.0]hexane-1-carboxaldehyde (8), (1,2,2-trimethyl-3-cyclopenten-1-yl)acetaldehyde (9), alpha-campholenealdehyde (10), photocitral A (3), epiphotocitral A (4), and photocitral B (5). New compounds of aldehyde 9, 6 and 10, were newly identified as photoreaction products of citral. Limonene, terpinolene, and nonanal decreased, while p-cymene increased after UV irradiation. Other components, such as sesquiterpene hydrocarbons, citronellal, linalool, and terpineols, were only slightly changed. These results suggested that citral is a more UV-unstable component in lemon flavor and the photolysis of citral could affect other components in lemon flavor during UV irradiation.
• Erman, M. B.; Volkova, O. O.; Cherkaev, G. V., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 12, p. 2252 - 2261
  作者：Erman, M. B.、Volkova, O. O.、Cherkaev, G. V.、Pribytkova, I. M.、Antipin, M. Yu.、et al.

  DOI：——

  日期：——
• EHRMAN M. B.; VOLKOVA O. O.; CHERKAEV G. V.; PRIBYTKOVA I. M.; ANTIPIN M.+, ZH. ORGAN. XIMII, 22,(1986) N 12, 2508-2519
  作者：EHRMAN M. B.、 VOLKOVA O. O.、 CHERKAEV G. V.、 PRIBYTKOVA I. M.、 ANTIPIN M.+

  DOI：——

  日期：——
• Catalytic Asymmetric Prins Bicyclization for the<i>endo</i>-Selective Formation of 2,6-dioxabicyclo[2.2.2]octanes
  作者：Jie Liu、Lijun Zhou、Chao Wang、Demin Liang、Zhiming Li、Yue Zou、Quanrui Wang、Andreas Goeke

  DOI：10.1002/chem.201600847

  日期：2016.4.25

  A new Lewis acid‐catalyzed endo‐selective Prins bicyclization of γ,δ‐unsaturated aldehydes or ketones with a broad range of aldehydes to dioxabicyclo[2.2.2]octanes is disclosed. When using a chiral BINOL‐derived N‐triflylphosphoramide (NTPA) as catalyst and glyoxylate esters as substrates, the cross‐dimerization afford functionalized bicyclic acetals with excellent diastereo‐ and enantioselectivities

  公开了一种新的路易斯酸催化的内含选择性的γ，δ-不饱和醛或酮的内环选择性Prins双环化成二氧杂双环[2.2.2]辛烷。当使用手性BINOL衍生的N-三flylphosphoramide（NTPA）作为催化剂和乙醛酸酯作为底物时，交叉二聚可提供具有出色的非对映异构和对映选择性的官能化双环缩醛。