(E)-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal S,S-acetal | 121846-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (E)-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal S,S-acetal
• 英文别名: 2-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]-1,3-dithiane
• CAS: 121846-23-9
• 化学式: C₁₅H₂₄S₂
• 分子量: 268.488
• InChiKey: JHFLJGZLAZYQJD-BQYQJAHWSA-N

物化性质

• 沸点：
  374.6±42.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal S,S-acetal 在 正丁基锂 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 为溶剂， 生成 (2E,4E,6E,8E)-7-(2-Hydroxy-ethyl)-3-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenal
  参考文献：
  名称：

  Probes which reflect the distance between the retinal chromophore and membrane surface in bacteriorhodopsin (bR). Direction of retinal 9-methyl in bR

  摘要：

  DOI：

  10.1021/ja00195a073

文献信息

• Retinoids and related compounds. Part 19.1 Syntheses of 9E- and 9Z-locked retinoic acid analogues and their transcriptional activities as ligands for retinoic acid receptors and retinoid X receptors
  作者：Yuko Katsuta、Yukiko Aoyama、Hisa Osone、Akimori Wada、Masayoshi Ito

  DOI：10.1039/a606719k

  日期：——

  Novel retinoic acid (RA) analogues, 9E-locked-RA 3 and 9Z-locked RA 4, have been synthesized in order to prohibit geometrical isomerization at the C(9)–C(10) double bond when these ligands interact with the retinoic acid receptor (RAR) and retinoid X receptor (RXR). Transcriptional activities of these analogues for RAR and RXR are also described.

  新型的全反式维甲酸（RA）类似物，9E-锁定-RA-3和9Z-锁定-RA-4，已被合成，目的是在它们与维甲酸受体（RAR）和类维甲酸X受体（RXR）相互作用时，阻止C(9)–C(10)双键的几何异构化。这些类似物对RAR和RXR的转录活性也被描述了。
• Synthesis of 9E- and 9Z-Locked Retinoic Acid Analogs As Ligands for RAR and RXR.
  作者：Yuko KATSUTA、Yukiko AOYAMA、Hisa OSONE、Akimori WADA、Shimami UCHIYAMA、Takuya KITAMOTO、Shoichi MASUSHIGE、Shigeaki KATO、Masayoshi ITO

  DOI：10.1248/cpb.42.2659

  日期：——

  New retinoic acid (RA) analogs 9E-locked-RA 3 and 9Z-locked-RA 4 were synthesized from dithiane 6 and beta-cyclocitral 13, respectively. Both analogs behaved as agonistic ligands for a mixture of retinoic acid receptor (RAR) and retinoid X receptor (RXR).

  新的视黄酸（RA）类似物9E-锁合的RA 3和9Z-锁合的RA 4分别由二噻吩6和β-环柠檬酸酯13合成。两种类似物均充当视黄酸受体（RAR）和类维生素X受体（RXR）混合物的激动配体。
• Retinoids and Related Compounds. Part 22. Synthesis of .BETA.-Ionone Analog Tricarbonyliron Complexes.
  作者：Akimori WADA、Naoko FUJIOKA、Masayoshi ITO

  DOI：10.1248/cpb.47.171

  日期：——

  The synthesis of β-ionone analog tricarbonyliron complexes was investigated. N-Methoxy-N-methyl-(2, 6, 6-trimethyl-1-cyclohexen-1-yl)-2-propenamide (Weinreb amide), prepared from the corresponding ethyl ester and N, O-dimethylhydroxylamine hydrochloride, reacted smoothly with various organometallic reagents to afford the β-ionone analogs in good to excellent yields. Treatment of these compounds with dodecacarbonyltriiron afforded the corresponding tricarbonyliron complexes in high yields.

  研究了β-紫罗兰酮类似物三羰基铁配合物的合成。由相应的乙酯与N,O-二甲基羟胺盐酸盐制备N-甲氧基-N-甲基-(2,6,6-三甲基-1-环己烯-1-基)-2-丙烯酰胺(Weinreb酰胺)，反应顺利与各种有机金属试剂反应，以良好至优异的产率提供 β-紫罗兰酮类似物。用十二羰基三铁处理这些化合物以高产率得到相应的三羰基三铁配合物。
• Synthesis of 11Z-9-demethyl-9-((3-indolyl)methyl)retinal
  作者：Akimori Wada、Naoko Fujioka、Masayoshi Ito

  DOI：10.1002/jhet.5570380138

  日期：2001.1

  A convenient synthesis of 11Z-9-demethyl-9-((3-indolyl)methyl)retinal, which has an amino acid residue of tryptophan at the 9 position in retinal, is described using a tricarbonyliron complex.

  使用三羰基铁配合物描述了一种方便合成的11Z-9-去甲基-9-（（3-吲哚基）甲基）视网膜，该视网膜在视网膜的9位具有色氨酸的氨基酸残基。
• Probes which reflect the distance between the retinal chromophore and membrane surface in bacteriorhodopsin (bR). Direction of retinal 9-methyl in bR
  作者：Myung Hwan Park、Toshihiro Yamamoto、Koji Nakanishi

  DOI：10.1021/ja00195a073

  日期：1989.6