(Z)-(3,3-二甲基环己亚基)-乙醛 | 26532-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (Z)-(3,3-二甲基环己亚基)-乙醛
• 英文名称: (Z)-2-(3,3-Dimethylcyclohexylidene)acetaldehyde
• 英文别名: Grandlure III；(2Z)-2-(3,3-dimethylcyclohexylidene)acetaldehyde
• CAS: 26532-24-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: TYHKWUGMKWVPDI-UITAMQMPSA-N

物化性质

• 沸点：
  226.6±9.0℃ (760 Torr)
• 密度：
  0.955±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  95.6±11.0℃
• 保留指数：
  1799;1799

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 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

安全信息

• 海关编码：
  2912299000

反应信息

• 作为产物：
  描述：

  2-(4-hydroxy-3,3-dimethylcyclohexylidene)ethyl formate 在 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 molecular sieve 、 4-甲基苯磺酸吡啶 、 间氯过氧苯甲酸 、 对甲苯磺酰肼 、 pyridinium chlorochromate 、 二苯基膦酸锂 、 碘甲烷 作用下， 以 乙醇 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 30.0h， 生成 (Z)-(3,3-二甲基环己亚基)-乙醛
  参考文献：
  名称：

  Mori, Kenji; Itou, Masamichi, Liebigs Annalen der Chemie, 1989, p. 969 - 974

  摘要：

  DOI：

文献信息

• The stereospecific formation of an exocyclic alkene by a consecutive radical cyclization-elimination
  作者：Francis L Harris、Larry Weiler

  DOI：10.1016/s0040-4039(00)96249-x

  日期：——

  The iodovinylstannanes 4 and 5 were prepared by the conjugate addition of the tri--butyltin moiety to a substituted propiolic ester. Compounds 4 and 5 underwent a radical cyclization-elimination reaction to stereospecifically generate an exocyclic alkene.

  碘代乙烯基锡烷4和5是通过将三丁基锡部分共轭加成到取代的丙酸酯上而制得的。化合物4和5进行自由基环化消除反应，以立体定向生成环外烯烃。
• Tandem Michael−Wittig−Horner Reaction: One-Pot Synthesis of δ-Substituted α,β-Unsaturated Carboxylic Acid Derivatives − Application to a Concise Synthesis of (Z)- and (E)-Ochtoden-1-al
  作者：Olivier Piva、Sébastien Comesse

  DOI：10.1002/1099-0690(200007)2000:13<2417::aid-ejoc2417>3.0.co;2-x

  日期：2000.7

  A new tandem Michael−Wittig−Horner reaction has been developed to produce in high yields δ-substituted α,β-unsaturated esters, amides and lactones. The reaction has been successfully applied to a concise synthesis of (E)- and (Z)-ochtoden-1-als, components of the male sex pheromone of boll weevil from 3-methylcyclohex-2-en-1-one.

  已经开发出一种新的串联 Michael-Wittig-Horner 反应以高产率生产 δ-取代的 α,β-不饱和酯、酰胺和内酯。该反应已成功应用于从 3-methylcyclohex-2-en-1-one 合成棉铃象甲雄性信息素的 (E)- 和 (Z)-ochtoden-1-als 组分。
• Synthetic Studies on the Ochtodane Type Terpenes I. Stereoselective Construction of the Ochtodane Skeleton from Myrcene
  作者：Yukio Masaki、Kinji Hashimoto、Kazuhiko Sakuma、Kenji Kaji

  DOI：10.1246/bcsj.57.3466

  日期：1984.12

  cyclization reaction was found to depend remarkably upon the reaction temperature and the 85–94% of E-stereoselectivity was attained at −78 °C. By the method, the ochtodane derivatives with the sulfur- or oxygen-functional groups on the C(6)-position were obtained. Synthetic applications of the ochtodane type compounds (12) and (19) to the aldehyde component (4) of the pheromone of the male boll weevils and

  奥克托丹骨架，1,1-二甲基-3-乙基环己烷 (1) 的碳骨架是通过酸催化（SnCl4 或 CF3CO2H）环化末端官能化的月桂烯衍生物，苯亚磺酰氯加合物 (7) 高度立体选择性地构建的，来自 7 的末端 β-羟基硫化物 (8) 和月桂烯 6,7-环氧化物 (10)。发现在环化反应中伴随形成的 1 中的 3-外双键的立体选择性显着取决于反应温度，并且在 -78°C 下达到 85-94% 的 E-立体选择性。通过该方法，获得了在C(6)-位上具有硫-或氧-官能团的奥克托丹衍生物。
• [EN] PROCESS OF PRODUCTION OF 1-(5,5-DIMETHYLCYCLOHEX-1-EN-1-YL)ETHANONE AND 1-(5,5-DIMETHYLCYCLOHEX-6-EN-1-YL)ETHANONE<br/>[FR] PROCÉDÉ DE PRODUCTION DE 1- (5,5-DIMÉTHYLCYCLOHEX -1-ÈN -1-YL)ÉTHANONE ET DE 1- (5,5-DIMÉTHYLCYCLOHEX -6-ÈN -1-YL)ÉTHANONE
  申请人：DSM IP ASSETS BV

  公开号：WO2015144832A1

  公开（公告）日：2015-10-01

  The present invention relates to an improved method for producing of 1-(5,5- dimethylcyclohex-1-en-1-yl)ethanone and 1-(5,5-dimethylcyclohex-6-en-1- yl)ethanone.

  本发明涉及一种改进的制备1-(5,5-二甲基环己-1-烯-1-基)乙酮和1-(5,5-二甲基环己-6-烯-1-基)乙酮的方法。
• Composition of grandlure and dichlorvos for attracting and killing boll weevils in boll weevil traps
  申请人：Plato Alfred Thomas

  公开号：US20050147634A1

  公开（公告）日：2005-07-07

  Compositions and methods for attracting, capturing and killing populations of cotton boll weevils ( Anthonomus grandis Boh. ) in boll weevil traps are disclosed. With respect to the attraction and capture of boll weevils with Grandlure, the synthetic pheromone of the cotton boll weevil, there is generally an increased number of boll weevils captured in the trap cylinder when an insecticide dispenser is included in the trap cylinder to kill the weevils and thus prevent their escape. Additionally, dead boll weevils are more accurately counted than live boll weevils. The compound dichlorvos (2,2-dichlorovinyl dimethyl phosphate or DDVP) is the most preferred among those few insecticides that can be used in traps for killing and preventing weevil escapes. This is also the preferred insecticide when combined with Grandlure in a single dispenser to kill boll weevils or inhibit their ability to develop normally and reproduce. The single Grandlure dichlorvos dispenser provides for significant savings in labor expenses in large area trapping and eradication programs and significantly reduces the disposal of waste materials from spent dispensers.

  用于吸引、捕捉和杀死棉铃象鼻虫（Anthonomus grandis Boh. Anthonomus grandis Boh. 棉铃象鼻虫）的组合物和方法。关于用棉铃象鼻虫的合成信息素 Grandlure 吸引和捕获棉铃象鼻虫，如果在诱捕筒中加入杀虫剂喷洒器杀死象鼻虫，从而防止它们逃跑，则诱捕筒中捕获的棉铃象鼻虫数量通常会增加。此外，死棉铃虫的计数比活棉铃虫更准确。敌敌畏（2,2-二氯乙烯基二甲基磷酸酯或 DDVP）是少数几种可用于诱捕器以杀死并防止象鼻虫逃逸的杀虫剂中最受欢迎的一种。当与格兰富（Grandlure）结合使用时，这也是杀死棉铃象鼻虫或抑制其正常发育和繁殖能力的首选杀虫剂。在大面积诱捕和根除计划中，单一的敌敌畏喷洒器可大大节省劳动力支出，并显著减少废喷洒器产生的废料处理量。