epiphotocitral A | 78963-10-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: epiphotocitral A
• 英文别名: (1R,2S,5S)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carbaldehyde
• CAS: 78963-10-7
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: JCDLXWAYWSJVTP-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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

• 作为产物：
  描述：

  顺式-柠檬醛 以 苯 为溶剂， 生成 epiphotocitral A
  参考文献：
  名称：

  Novel temperature-dependent photochemical rearrangement of citral

  摘要：

  DOI：

  10.1021/ja00474a061

文献信息

• A remarkably simple α-oximation of aldehydes via organo-SOMO catalysis
  作者：Patrizia Gentili、Silvia Pedetti

  DOI：10.1039/c2cc31566a

  日期：——

  A novel α-oximation reaction of unactivated aldehydes has been achieved in excellent yields by reaction with NaNO2–FeCl3 couple and in the presence of pyrrolidine as organocatalyst.

  已通过与NaNO2–FeCl3耦合反应，并在吡咯烷作为有机催化剂的存在下，成功实现了未激活醛的全新α-氧化反应，且产率优秀。
• Mn(III)-based oxidative free radical cyclizations of unsaturated 2-cyclohexenones and aldehydes
  作者：Barry B Snider、Eugenia Y Kiselgof

  DOI：10.1016/0040-4020(96)00234-7

  日期：1996.4

  Oxidative free-radical cyclizations of unsaturated 2-cyclohexenones 9a, 9b, 17, and 24 with Mn(OAc)3 afford unsaturated α′-keto radicals such as 10 that cyclize to afford bicyclic products. The major process with 2-cyclohexenone 27 is conjugate addition of acetate to form β-acetoxy α-keto radical 37. Unsaturated aldehydes 45, 57a, and 57b are oxidized to radicals that cyclize to give cyclopentane- and

  不饱和2-环己烯酮9a，9b，17和24与Mn（OAc）3的氧化自由基环化产生不饱和α'-酮基，例如10，其环化以提供双环产物。用2-环己烯酮27的主要过程是共轭添加乙酸盐以形成β-乙酰氧基α-酮基37。不饱和醛45、57a和57b被氧化为可环化的自由基，生成环戊烷和环己烷羧醛。
• Novel photochemical rearrangements of citral and related compounds at elevated temperatures
  作者：Steven Wolff、Francis Barany、William C. Agosta

  DOI：10.1021/ja00527a041

  日期：1980.3
• 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.
• Syntheses and carbon-13 NMR spectra of trans, cis- and trans,trans-nepetalinic acids and photocitral A
  作者：Takashi Sakai、Ken Morita、Chigako Matsumura、Akio Sudo、Sadao Tsuboi、Akira Takeda

  DOI：10.1021/jo00336a030

  日期：1981.11