1,3,3-三甲基-2-[(1E,3E)-3-甲基-1,3-己二烯-5-炔基]-环己烷 | 25576-25-4

• 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: 1,3,3-三甲基-2-[(1E,3E)-3-甲基-1,3-己二烯-5-炔基]-环己烷
• 中文别名: 1,3,3-三甲基-2-[（（1E，3E）-3-甲基-1,3-己二-5-炔基]-环己烷
• 英文名称: (3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne
• 英文别名: 6-<2,6,6-Trimethyl-cyclohexen-(1)-yl>-4-methylhexadien-(3,5)-in-(1)；1,3,3-trimethyl-2-(3-methyl-hexa-1,3-dien-5-ynyl)-cyclohexene；1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene；1,3,3-Trimethyl-2-[(1E,3E)-3-methyl-1,3-hexadien-5-ynyl]-cyclohexane；1,3,3-trimethyl-2-[(1E,3E)-3-methylhexa-1,3-dien-5-ynyl]cyclohexene
• CAS: 25576-25-4
• 化学式: C₁₆H₂₂
• 分子量: 214.351
• InChiKey: VZHBEOMOYZVQPM-OGFJCPFKSA-N

物化性质

• 沸点：
  299.2±9.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、己烷

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3,3-三甲基-2-[(1E,3E)-3-甲基-1,3-己二烯-5-炔基]-环己烷 在 氢氧化钾 、 nBu₃Sn(nBu)Cu(CN)Li₂ 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 维A酸
  参考文献：
  名称：

  烯基锡烷与三氟甲磺酸乙烯酯的钯催化偶联反应立体控制合成13-取代维甲酸

  摘要：

  一种新的立体选择性合成全E-、13Z-和9Z-维甲酸酯的方法，通过钯催化的四烯基锡与E型或Z型乙烯基三氟甲磺酸酯的交叉耦合反应，产率良好。应用此方法，成功以满意的产率制备了13-取代的全E-和9Z-维甲酸。

  DOI：

  10.1055/s-2001-14908
• 作为产物：
  描述：

  4-(1,4-二甲基-1-乙基)戊基酚 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1,3,3-三甲基-2-[(1E,3E)-3-甲基-1,3-己二烯-5-炔基]-环己烷
  参考文献：
  名称：

  Accurate Measurements of ¹³C−¹³C J-Couplings in the Rhodopsin Chromophore by Double-Quantum Solid-State NMR Spectroscopy

  摘要：

  A new double-quantum solid-state NMR pulse sequence is presented and used to measure one-bond 13C-13C J-couplings in a set of 13C2-labeled rhodopsin isotopomers. The measured J-couplings reveal a perturbation of the electronic structure at the terminus of the conjugated chain but show no evidence for protein-induced electronic perturbation near the C11-C12 isomerization site. This work establishes NMR methodology for measuring accurate 1JCC values in noncrystalline macromolecules and shows that the measured J-couplings may reveal local electronic perturbations of mechanistic significance.

  DOI：

  10.1021/ja0581604

文献信息

• Carboxylate-Directed Tandem Functionalisations of α,β-Dihaloalkenoic Acids with 1-Alkynes: A Straightforward Access to (Z)-Configured, α,β-Substituted γ-Alkylidenebutenolides
  作者：Samuel Inack Ngi、Khalil Cherry、Virginie Héran、Laurent Commeiras、Jean-Luc Parrain、Alain Duchêne、Mohamed Abarbri、Jérôme Thibonnet

  DOI：10.1002/chem.201102570

  日期：2011.12.2

  and stereoselectively leads to rarely described (Z)‐3‐halo‐5‐ylidene‐5H‐furan‐2‐ones. These compounds are subsequently able to undergo classical Pd‐catalysed cross‐coupling reactions, providing 3‐substituted and 3,4‐disubstituted 5‐ylidene‐5H‐furan‐2‐ones (see scheme).

  容易和温和的铜（I）催化的易获得的（E）-2,3-二卤代丙酸衍生物的区域选择性和立体选择性内酯化导致很少描述的（Z）-3-卤代-5-亚烷基-5 H-呋喃- 2个 这些化合物随后能够进行经典的Pd催化的交叉偶联反应，提供3-取代的和3,4-二取代的5-亚烷基-5 H-呋喃-2-（参见方案）。
• Preparation and biological activity of 13-substituted retinoic acids
  作者：Akimori Wada、Kouki Fukunaga、Masayoshi Ito、Yukari Mizuguchi、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2004.04.047

  日期：2004.7

  13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Olive; Mousseron-Canet; Dornand, Bulletin de la Societe Chimique de France, 1969, vol. 9, p. 3247 - 3252
  作者：Olive、Mousseron-Canet、Dornand

  DOI：——

  日期：——
• Kabbe,H.-J. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 684, p. 14 - 24
  作者：Kabbe,H.-J. et al.

  DOI：——

  日期：——
• Syntheses of 13C2-labelled 11Z-retinals
  作者：Neville J. McLean、Axel Gansmuller、Maria Concistre、Lynda J. Brown、Malcom H. Levitt、Richard C.D. Brown

  DOI：10.1016/j.tet.2011.07.092

  日期：2011.10

  To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent C-13 labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a C-13-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a C-13-containing ethoxy Bestmann-Ohira reagent. The C-13 labels at C10 and C11 were introduced through the reaction of beta-ionone with labelled triethyl phosphonoacetate. (C) 2011 Elsevier Ltd. All rights reserved.