r-1-ethyl-5-hydroxy-c-3-(4-hydroxy-5-methoxyphenyl)-6-methoxy-t-2-methylindane | 522-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: r-1-ethyl-5-hydroxy-c-3-(4-hydroxy-5-methoxyphenyl)-6-methoxy-t-2-methylindane
• 英文别名: γ-diisoeugenol；(+/-)-1r-ethyl-3c-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-2t-methyl-indan-5-ol；(+/-)-1r-Aethyl-3c-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-2t-methyl-indan-5-ol；(+/-)-6-Methoxy-2t-methyl-1r-aethyl-3c-(4-hydroxy-3-methoxy-phenyl)-indanol-(5)；(1S,2S,3S)-1-ethyl-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methyl-2,3-dihydro-1H-inden-5-ol
• CAS: 522-09-8；15161-78-1；76155-30-1；140696-12-4
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: QSYFPBASFNGQSF-LOOLNKMNSA-N

物化性质

• 熔点：
  179-180℃
• 沸点：
  220 °C(Press: 4 Torr)
• 密度：
  1.151
• LogP：
  4.456 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  r-1-ethyl-5-hydroxy-c-3-(4-hydroxy-5-methoxyphenyl)-6-methoxy-t-2-methylindane 在 sodium hydroxide 、 sodium acetate 作用下， 生成 (+/-)-5-ethoxy-3c-(4-ethoxy-3-methoxy-phenyl)-1r-ethyl-6-methoxy-2t-methyl-indan
  参考文献：
  名称：

  Mueller; Kucsman, Chemische Berichte, 1954, vol. 87, p. 1747,1751

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 在 silica gel supported sulfuric acid 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以80%的产率得到r-1-ethyl-5-hydroxy-c-3-(4-hydroxy-5-methoxyphenyl)-6-methoxy-t-2-methylindane
  参考文献：
  名称：

  First green protocols for the large-scale preparation of γ-diisoeugenol and related dihydro(1H)indenes via formal [3+2] cycloaddition reactions

  摘要：

  Trans-isoeugenol and related styrenes (trans-isohomogenol or C-benzylated isoeugenol), important components of the essential oil of various tropical plants, dimerize easily in the presence of catalytic amounts of BF(3)center dot OEt(2) in poly(ethylene glycol) with M(n) = 400 (PEG-400) or SiO(2)-OSO(3)H in MeCN via formal [3+2] cycloaddition reaction to give respective natural products (diisoeugenol and its O-substituted analog) with the 1,2-trans-2,3-trans-configuration in excellent yields. gamma-Diisoeugenol scale-up preparation has also been described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.038

文献信息

• Stereocontrolled syntheses of (−)- and (+)-γ-diisoeugenol along with optically active eight stereoisomers of 7,8′-epoxy-8,7′-neolignan
  作者：Tatsuaki Takubo、Nao Kikuchi、Hisashi Nishiwaki、Satoshi Yamauchi

  DOI：10.1039/d1ob00008j

  日期：——

  Friedel–Crafts reaction gave exclusively indane with (7S,7′S,8R,8′R)-2,7′-cyclo-7,8′-neolignan structure 18 along with (7S,7′R,8S,8′R)-7,8′-epoxy-8,7′-neolignan structure 19. Indane 18 was converted to (−)-γ-diisoeugenol ((−)-4). On the other hand, (2S,3R,4R,5S)-3,5-bis(4-benzyloxy-3-methoxyphenyl)-2,4-dimethyltetrahydro-3-furanol 22 did not afford indane, but the tetrahydrofuran structure with (7S,7′S,8S,8′S)-7

  结果表明，（2 R，3 S，4 R，5 S）-3,5-双（4-苄氧基-3-甲氧基苯基）-2,4-二甲基四氢-3-呋喃醇的叔苄基羟基还原17，随后分子内Friedel-Crafts反应，得到二氢化茚只与（7小号，7'小号，8 - [R，8' - [R）-2,7'-环7,8'-新木脂素结构18具有沿（7小号， 7' - [R，8小号，8' - [R）-7,8'环氧8,7'-新木脂素结构19。茚满18转化为（-）-γ-二异丁香酚（（-）- 4）。另一方面，（2 S，3 R，4 R，5 S）-3,5-双（4-苄氧基-3-甲氧基苯基）-2,4-二甲基四氢-3-呋喃醇22没有提供茚满，但具有（7 S，7 'S，8 S，8 'S）-7,8'-环氧-8,7'-neolignan结构23和7'- epi - 23的四氢呋喃结构。
• Gold-Catalyzed Dimeric Cyclization of Isoeugenol and Related 1-Phenylpropenes in Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of 1,2,3-Trisubstituted 2,3-Dihydro-1H-indenes
  作者：Nobuyoshi Morita、Osamu Tamura、Rie Mashiko、Dai Hakuta、Daisuke Eguchi、Shintaro Ban、Yoshimitsu Hashimoto、Iwao Okamoto

  DOI：10.1055/s-0035-1561604

  日期：——

  Abstract Gold-catalyzed dimerization of isoeugenol and related 1-phenylpropenes in ionic liquid enabled environmentally friendly, stereo­selective synthesis of 1,2,3-trisubstituted 2,3-dihydro-1H-indenes. Dimerization of isoeugenol or isohomogenol afforded diisoeugenol or diisohomogenol, respectively, with α-configuration, whereas dimerization of α-asarone furnished diasarone with γ-configuration.

  摘要 异丁香酚和相关的1-苯基丙烯在离子液体中的金催化二聚能够实现1,2,3-三取代的2,3-二氢-1 H-茚的环保，立体选择性合成。异丁香酚或异丁香酚的二聚分别得到具有α-构型的二异丁香酚或二异丁香酚，而α-asaron的二聚化提供了具有γ-构型的diasarone。 异丁香酚和相关的1-苯基丙烯在离子液体中的金催化二聚能够实现1,2,3-三取代的2,3-二氢-1 H-茚的环保，立体选择性合成。异丁香酚或异丁香酚的二聚分别得到具有α-构型的二异丁香酚或二异丁香酚，而α-asaron的二聚化提供了具有γ-构型的diasarone。
• Gold-Catalyzed Formal (3+2) Cycloaddition in an Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of Polysubstituted Indanes from Benzylic Alcohols and 1-Phenylpropenes
  作者：Nobuyoshi Morita、Osamu Tamura、Hitomi Chiaki、Kanae Ikeda、Kosaku Tanaka、Yoshimitsu Hashimoto

  DOI：10.1055/a-2002-4122

  日期：——

  A gold-catalyzed formal (3+2) cycloaddition of benzylic alcohols with 1-phenylpropenes in an ionic liquid permits the environmentally friendly stereoselective synthesis of polysubstituted indanes in good yields and with high selectivity. The gold catalyst can be recycled at least five times.

  在离子液体中，金催化的苄醇与 1-苯基丙烯的形式 (3+2) 环加成允许以良好的收率和高选择性环境友好地立体选择性合成多取代的茚满。金催化剂至少可以循环使用五次。
• Yamashita; Funakubo, Technology Reports of the Osaka University, 1957, vol. 7, p. 169,171
  作者：Yamashita、Funakubo

  DOI：——

  日期：——
• Yamashita, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1942, vol. 63, p. 1333
  作者：Yamashita

  DOI：——

  日期：——