6-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛 | 59742-20-0

• 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
• 中文名称: 6-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛
• 中文别名: 肼,[(4-甲氧基-3-甲基苯基)甲基]-
• 英文名称: 6-methyl-4-(4'-methyl-3'-pentenyl)-3-cyclohexenecarbaldehyde
• 英文别名: 6-methyl-4-(4-methylpent-3-enyl)cyclohex-3-enecarbaldehyde；6-methyl-4-(4-methyl-pent-3-enyl)-cyclohex-3-enecarbaldehyde；6-Methyl-4-(4-methyl-pent-3-enyl)-cyclohex-3-encarbaldehyd；6-methyl-4-(4-methyl-3-pentenyl)cyclohex-3-ene-1-carbaldehyde；6-methyl-4-(4-methylpent-3-enyl)cyclohex-3-ene-1-carbaldehyde
• CAS: 59742-20-0
• 化学式: C₁₄H₂₂O
• mdl: MFCD00447502
• 分子量: 206.328
• InChiKey: LDZKQVMZNGHEAT-UHFFFAOYSA-N

物化性质

• 沸点：
  117 °C(Press: 1.5 Torr)
• 密度：
  0.9198 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.642
• 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：

  6-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛 在 草酰氯 、 高氯酸,吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of α-hydroxy(polyprenyl) bisphosphonates

  摘要：

  Bisphosphonates derived from natural terpenes were synthesized by phosphonylation of corresponding aldehydes. The general strategy of introduction of the phosphonate groups into the polyprenol molecule involves successive treatment of a hydroxyl compound by Swern reagent to oxidize the C-OH group into C=O and a (EtO)(3)P/[PyH]+ClO (-) (4) mixture to phosphylate the resulting carbonyl compound.

  DOI：

  10.1134/s1070363214040082
• 作为产物：
  描述：

  月桂烯 、 丁烯-2-醛 生成 6-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛
  参考文献：
  名称：

  Diels; Alder, Justus Liebigs Annalen der Chemie, 1929, vol. 470, p. 103

  摘要：

  DOI：

文献信息

• Unsaturated Aldehydes as Alkene Equivalents in the Diels–Alder Reaction
  作者：Esben Taarning、Robert Madsen

  DOI：10.1002/chem.200800003

  日期：2008.6.20

  A one-pot procedure is described for using alpha,beta-unsaturated aldehydes as olefin equivalents in the Diels-Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-withdrawing substituents. In this way, the aldehyde group serves as a traceless control element

  描述了一种一锅法，该方法用于在Diels-Alder反应中使用α，β-不饱和醛作为烯烃当量。该方法将正常的电子需求环加成反应与醛二烯亲和剂和铑催化的醛脱羰反应结合在一起，得到不具有吸电子取代基的环己烯。以这种方式，醛基用作指导环加成反应的无痕控制元素。在催化量的三氟化硼醚化物的存在下，在二甘醇二甲醚溶液中进行Diels-Alder反应。随后路易斯酸的淬灭，添加0.3％的[Rh（dppp）2 Cl]并加热至回流实现了随后的脱羰作用，得到了环己烯产物。在这些条件下，丙烯醛，巴豆醛和肉桂醛已与多种1，3-二烯可提供环己烯的总收率在53％到88％之间。在这些转化中，这三种醛分别相当于乙烯，丙烯和苯乙烯。
• New Catalyst for Phosphonylation of C˭X Electrophiles
  作者：Oleg I. Kolodiazhnyi、Olga O. Kolodiazhna

  DOI：10.1080/00397911.2010.542602

  日期：2012.6

  recyclable catalyst for the reaction of trialkyl phosphites with various C˭X electrophiles (aldehydes, ketones, ketophosphonates, imines, isocyanates, isothiocyanates, activated alkenes) to afford corresponding α-substituted phosphonates in good yields. The main advantages of the new catalyst is strong activity, accessibility, good yields of products, and gentle conditions of reaction. GRAPHICAL ABSTRACT

  摘要 高氯酸吡啶是一种高效且可回收的催化剂，可用于亚磷酸三烷基酯与各种 C˭X 亲电子试剂（醛、酮、酮膦酸酯、亚胺、异氰酸酯、异硫氰酸酯、活性烯烃）反应，以良好的收率得到相应的 α-取代膦酸酯。 . 新型催化剂的主要优点是活性强、易接近、产物收率好、反应条件温和。图形概要
• New Carbonyl Compounds in the High-Boiling Fraction of Lavender Oil. 3rd Communication
  作者：Roman Kaiser、Dietmar Lamparsky

  DOI：10.1002/hlca.19840670503

  日期：1984.8.8

  The occurrence of a series of new constituents which can be considered as Diels-Alder adducts of methyl vinyl ketone and ocimene (1–4), myrcene (9, 10) or β-far-nesene ( 11, 12), respectively, was reported. Furthermore, the structures of four isomeric cyclohexene derivatives could be established as adducts 21–24 of (E, Z)- and (E, E)-1,3,5-undecatrience and methyl vinyl ketone. Another series of constituents

  了一系列新的组成部分，它们可以被认为是发生狄尔斯-阿德耳甲基乙烯基酮和罗勒烯（1-4），月桂烯（加合物9，10）或β-远nesene（11，12）分别是报告。此外，可以建立四种异构体环己烯衍生物的结构，作为（E，Z） -和（E，E）-1,3,5-不饱和度与甲基乙烯基酮的加合物21-24。具有降冰片烷骨架的另一系列成分分别代表甲基环戊二烯和1-辛烯-3-酮或甲基乙烯基酮的加合物25-32和33-40。依据阿尔德的内切-rule的内-异构体是占优势的天然以及在合成混合物。这些成分中的大多数也可以在绝对薰衣草以及新鲜制备的薰衣草花己烷提取物中（Lavandula officinalis CHAIX）进行鉴定。
• ——
  作者：E. A. Dikusar、N. G. Kozlov、K. L. Moiseichuk、A. P. Yuvchenko

  DOI：10.1023/a:1013175911137

  日期：——

  A method was developed for preparation of alkynyl peroxides from terpene and steroid aldehydes and ketones by reaction of lithium peroxyacetylides with the corresponding aldehydes and ketones followed by treating the intermediate lithium alcoholates with acyl chlorides.
• Pyridinium perchlorate: A new catalyst for the reaction of trialkyl phosphites with the C=X electrophiles
  作者：O. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s107036321102006x

  日期：2011.2

  Pyridinium perchlorate is an effective catalyst for the reaction of trialkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, imines, isocyanates, isothiocyanates, and activated alkenes. The reaction leads to the formation of alpha-substituted phosphonates in a high yield. Advantages of the new catalyst are its high activity, availability, high product yields, and mild reaction conditions.