(+/-)-curcumene ether | 42482-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-curcumene ether
• 英文别名: 3,4,5,6-tetrahydro-2,2,6-trimethyl-6-(4-methylphenyl)-2H-pyran；2,2,6-trimethyl-6-(p-tolyl)tetrahydro-2H-pyran；2,2,6-trimethyl-6-p-tolyl-tetrahydro-pyran；2,2,6-Trimethyl-6-(4-methylphenyl)oxane
• CAS: 42482-66-6
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: NKSUFXDOOSPKIX-UHFFFAOYSA-N

物化性质

• 沸点：
  296.7±19.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-甲基-2-氧代庚-5-烯酸 在 tris(dibenzylideneacetone)dipalladium (0) 盐酸 、 4-二甲氨基吡啶 、 pentamethylpiperidine 、 氨 、 lithium 、 sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， -78.0~100.0 ℃ 、101.33 kPa 条件下， 反应 158.5h， 生成 (+/-)-curcumene ether
  参考文献：
  名称：

  Synthesis of (+/-)-Curcumene Ether

  摘要：

  以 5-溴-2-甲基-2-戊烯和 2-氨基-5-甲基苯酚为起始原料，通过分子内 Heck 反应生成一个立体的季中心，经过 9 个步骤合成了 (+/-)- 苝醚，总收率为 7%。

  DOI：

  10.1055/s-2003-40343

文献信息

• Electrochemical Phenylselenoetherification as a Key Step in the Synthesis of (±)-Curcumene Ether
  作者：Dragana Stevanović、Anka Pejović、Ivan S. Damljanović、Mirjana D. Vukićević、Georgi Dobrikov、Vladimir Dimitrov、Marija S. Denić、Niko S. Radulović、Rastko D. Vukićević

  DOI：10.1002/hlca.201200610

  日期：2013.6

  Two variants of a new pathway for the synthesis of (±)‐curcumene ether are described. The key steps in these procedures are intramolecular cyclizations of 6‐methyl‐2‐(4‐methylphenyl)hept‐6‐en‐2‐ol and 2‐methyl‐6‐(4‐methylphenyl)hept‐6‐en‐2‐ol by means of an electrochemically generated phenylselenyl cation. This synthetic approach provides significantly better yields than the previously reported protocols

  描述了合成（±）-姜黄烯醚的新途径的两个变体。这些程序中的关键步骤是6-甲基-2-（4-甲基苯基）庚-6-烯-2-醇和2-甲基-6-（4-甲基苯基）庚-6-烯-2-分子的分子内环化借助电化学产生的苯基硒烯基阳离子。与以前报道的方案相比，这种合成方法提供了明显更好的产量。
• Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis
  作者：Rong‐De He、Yunfei Bai、Guan‐Yu Han、Zhen‐Zhen Zhao、Xiaobo Pang、Xiaobo Pan、Xue‐Yuan Liu、Xing‐Zhong Shu

  DOI：10.1002/anie.202114556

  日期：2022.1.21

  A new C−C bond-forming reaction between alkenyl acetates and alkyl bromides was achieved by reductive nickel catalysis. This method offers very mild reaction conditions for facile and precise synthesis of structurally versatile aliphatic alkenes using readily available and stable alkenyl reagents. It allows for a gram-scale reaction and modification of biologically active molecules, and it affords

  通过还原镍催化，实现了乙酸烯基酯和烷基溴之间的新 C-C 键形成反应。该方法提供了非常温和的反应条件，可以使用易于获得且稳定的烯基试剂轻松和精确地合成结构通用的脂肪族烯烃。它允许对生物活性分子进行克级反应和修饰，并提供有用的构建块。
• Kametani, Tetsuji; Kawamura, Kuniaki; Tsubuki, Masayoshi, Journal of the Chemical Society. Perkin transactions I, 1984, p. 1305 - 1310
  作者：Kametani, Tetsuji、Kawamura, Kuniaki、Tsubuki, Masayoshi、Honda, Toshio

  DOI：——

  日期：——
• Compositions and Methods to Attract the Brown Marmorated Stink Bug (BMSB), Halyomorpha halys
  申请人：Secretary of Agriculture United States of America as Represented by the

  公开号：US20140161764A1

  公开（公告）日：2014-06-12

  A composition (useful for attracting Halyomorpha halys ) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols:trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl(2E,4E,6Z)-decatrieonate. Also a method for attracting Halyomorpha halys to an object or area, involving treating said object or area with a Halyomorpha halys attracting composition containing a Halyomorpha halys attracting effective amount of the composition.
• US9451771B2
  申请人：——

  公开号：US9451771B2

  公开（公告）日：2016-09-27