caronic aldehyde | 87334-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: caronic aldehyde
• 英文别名: caronaldehyde；2-[(1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetaldehyde
• CAS: 87334-38-1
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: DINMJPWMECTCJA-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  caronic aldehyde 在 palladium on activated charcoal sodium periodate 、 四氧化锇 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 25.0 ℃ 、8.11 MPa 条件下， 反应 30.0h， 生成 ethyl 7-oxo-5R,6S-dimethylmethanoheptanoate
  参考文献：
  名称：

  Tolstikov, G. A.; Miftakhov, M. S.; Tolstikov, A. G., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 11, p. 2076 - 2081

  摘要：

  DOI：
• 作为产物：
  描述：

  δ-3-carene 在 臭氧 、 ring-opening metathesis polymer-supported triphenylphosphine 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 2.0h， 以99%的产率得到caronic aldehyde
  参考文献：
  名称：

  ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis

  摘要：

  [GRAPHICS]ROMPgel-supported triphenylphosphine was synthesized in three steps (67%) from norbornadiene, 4-bromoiodobenzene, and chlorodiphenylphosphine. The supported reagent has a high loading (2.5 mmol/g) and favorable swelling properties in organic solvents. It has been utilized for the conversion of alcohols to halides, the reduction of ozonides, and the isomerization of alpha,beta-acetylenic esters and in the Staudinger reaction. In general, filtration of the resin from the reaction mixtures and evaporation gave the corresponding products in high yield and purity.

  DOI：

  10.1021/ol026008q

文献信息

• Carboxylic Acids in Secondary Aerosols from Oxidation of Cyclic Monoterpenes by Ozone
  作者：Marianne Glasius、Maria Lahaniati、Aggelos Calogirou、Dario Di Bella、Niels R. Jensen、Jens Hjorth、Dimitrios Kotzias、Bo R. Larsen

  DOI：10.1021/es990445r

  日期：2000.3.1

  Carboxylic acids are highly polar and have lower vapor pressures than their corresponding aldehydes and may thus play an important role in secondary organic aerosol formation processes. The most abundant carboxylic acids were the following:  cis-pinic acid AB1 (cis-3-carboxy-2,2-dimethylcyclobutylethanoic acid) from α- and β-pinene; cis-pinonic acid A3 (cis-3-acetyl-2,2-dimethylcyclobutylethanoic acid)

  已经进行了一系列烟雾室实验，其中五种环状单萜被臭氧氧化。通过 GC-MS 和 HPLC-MS 分析释放的二次气溶胶中的非挥发性极性氧化产物，重点是羧酸的鉴定。在对应于低百分比摩尔产率的浓度水平下测定了三类化合物：即二羧酸、氧代羧酸和羟基酮羧酸。羧酸具有高极性，并且比其相应的醛具有更低的蒸气压，因此可能在二次有机气溶胶形成过程中发挥重要作用。最丰富的羧酸如下：来自α-和β-蒎烯的顺式松香酸AB1（顺式-3-羧基-2,2-二甲基环丁基乙酸）；cis-pinonic acid A3 (cis-3-acetyl-2, 来自α-蒎烯和β-蒎烯的2-二甲基环丁基乙酸）和顺-10-羟基松香酸AB6（顺-2,2-二甲基-3-羟基乙酰环丁基乙酸）；cis-3-caric acid C1 (ci...
• Synthetic Approaches to Optically Active Macrolides Containing Hydrazide Fragments of L-(+)-Tartaric Acid from (+)-3-Carene, (+)-α-Pinene, and S-(–)-Limonene
  作者：G. Yu. Ishmuratov、M. P. Yakovleva、M. A. Shutova、R. R. Muslukhov、N. M. Ishmuratova、A. G. Tolstikov

  DOI：10.1007/s10600-014-1046-1

  日期：2014.10

  An optically pure macrolide containing 1,3-dioxolane, gem-dimethylcyclopropyl, and hydrazide fragments was synthesized from (+)-3-carene via [1+1]-condensation of the product from sequential ozonolysis—reduction and Tishchenko disproportionation of (3S,4S)-[(3R,4R)-4-isopropyl-3-methyl-6-oxoheptyl]-4-isopropyl-3-methyl-6-oxoheptanoate with the hydrazide of L-(+)-tartaric acid acetonide.

  一种光学纯的大环内酯，含有1,3-二氧戊环、宝石-二甲基环丙基和酰肼片段，由（+）-3-蒈烯通过（3S,4S）-（（3R,4R）-4-异丙基-3-甲基-6-氧代庚基）-4-异丙基-3-甲基-6-氧代庚酸乙酰肼与L-（+）-酒石酸乙酰肼的顺序臭氧分解-还原和季申科歧化反应的产物通过[1+1]缩合合成。
• A simple procedure for C–C bond cleavage of aromatic and aliphatic epoxides with aqueous sodium periodate under ambient conditions
  作者：Caitlin M. Binder、Darryl D. Dixon、Erik Almaraz、Marcus A. Tius、Bakthan Singaram

  DOI：10.1016/j.tetlet.2008.02.142

  日期：2008.4

  The sodium periodate mediated oxidative cleavage of the C-C bond of 12 epoxides is reported with yields of the corresponding carbonyl compounds in up to 91%. This is a two-step reaction that proceeds through a rate-limiting epoxide opening to a vicinal diol that is cleaved in situ to the corresponding carbonyl compound. This method serves as a chemoselective alternative to ozonolysis. (D 2008 Elsevier Ltd. All rights reserved.
• Kozlowska, Margarita; Sobotka, Wieslaw, Polish Journal of Chemistry, 1980, vol. 54, # 5, p. 957 - 962
  作者：Kozlowska, Margarita、Sobotka, Wieslaw

  DOI：——

  日期：——
• BHOSALE, S. S.;KULKARNI, G. H., CURR. SCI., 58,(1989) N0, C. 561-562
  作者：BHOSALE, S. S.、KULKARNI, G. H.

  DOI：——

  日期：——