(3S,5S)-alpinikatin | 1337550-58-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3S,5S)-alpinikatin
• 英文别名: (E,3S,5S)-7-(4-hydroxyphenyl)-1-phenylhept-1-ene-3,5-diol
• CAS: 1337550-58-9
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: AYBIGQXPQKLLGC-MQESYYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S)-alpinikatin 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 、 氘代吡啶 作用下， 反应 4.0h， 生成 [(E,3S,5S)-1-(4-hydroxyphenyl)-7-phenyl-5-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyhept-6-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Diarylheptanoids from the Seeds of Alpinia katsumadai as Heat Shock Factor 1 Inducers

  摘要：

  Seven new diarylheptanoids, (-)-(R)-4 ''-hydroxyyashabushiketol (1), (3S,5S)-alpinikatin (2), katsumain C (3), 7-epi-katsumain C (4), ent-alpinnanin B (5), ent-alpinnanin A (6), and ent-calyxin H (8), were isolated from the EtOAc extract of the seeds of Alpinia katsumadai together with three known compounds, alpinnanin B (7), epicalyxin H (9), and calyxin H (10). Each isomer mixture of 3 and 4,5-7, and 8-10 was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (3 and 4, 5-7, 8-10) at 1 mu M increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 M. Compounds 1 and 2 did not affect the induction of HSF1 protein.

  DOI：

  10.1021/np200355n
• 作为产物：
  描述：

  (S)-1-(4-(benzyloxy)phenyl)hex-5-en-3-ol 在 咪唑 、 sodium periodate 、 四氧化锇 、 diethylzinc 、 四氯化钛 、 N-甲基吗啉氧化物 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 37.5h， 生成 (3S,5S)-alpinikatin
  参考文献：
  名称：

  （3S，5S）-1,7-双（4-羟基苯基）庚烷-3,5-二醇，（3S，5S）-Alpinikatin及其非对映异构体的立体选择性全合成

  摘要：

  立体选择性合成二芳基庚烷，（3 S，5 S）-1,7-双（4-羟基苯基）庚烷-3,5-二醇（1），（3 S，5 S）-高山吡啶（3）及其它们的立体选择性合成非对映异构体（分别为2和4）是从现成的4-羟基苯甲醛制得的。合成序列涉及布朗斯的烯丙基化和Et 2 Zn介导的非对映选择性炔基化反应为关键步骤。

  DOI：

  10.1002/hlca.201500073

文献信息

• Lewis Acid Catalyzed Synthesis of Cyclic Carbonates, Precursors of 1,2- and 1,3-Diols
  作者：Johan Cornil、Laurine Gonnard、Amandine Guérinot、Sébastien Reymond、Janine Cossy

  DOI：10.1002/ejoc.201402557

  日期：2014.8

  An eco-friendly synthesis of cyclic carbonates through a Lewis acid catalyzed cyclization of tert-butyl carbonates is described. These cyclic carbonates are precursors of 1,2- and 1,3-diols, and the developed method was applied to a short synthesis of a diarylheptanoid, (3S,5S)-alpinikatin.

  描述了通过路易斯酸催化的碳酸叔丁酯环化合成环状碳酸酯的环保方法。这些环状碳酸酯是 1,2- 和 1,3- 二醇的前体，所开发的方法应用于二芳基庚烷类化合物 (3S,5S)-alpinikatin 的短程合成。
• Stereoselective Total Synthesis of (3<i>S</i>,5<i>S</i>)-1,7-Bis(4-hydroxyphenyl)heptane-3,5-diol, (3<i>S</i>,5<i>S</i>)-Alpinikatin, and Its Diastereoisomers
  作者：Kunuru Venkatesham、Sudina Purushotham Reddy、Baggu Chinnababu、Katragadda Suresh Babu

  DOI：10.1002/hlca.201500073

  日期：2015.9

  Stereoselective synthesis of the diarylheptanoids, (3S,5S)‐1,7‐bis(4‐hydroxyphenyl)heptane‐3,5‐diol (1), (3S,5S)‐alpinikatin (3), and their diastereoisomers (2 and 4, resp.), was achieved from readily available 4‐hydroxybenzaldehyde. The synthetic sequences involve Browns's allylation and Et2Zn mediated diastereoselective alkynylation reaction as key steps.

  立体选择性合成二芳基庚烷，（3 S，5 S）-1,7-双（4-羟基苯基）庚烷-3,5-二醇（1），（3 S，5 S）-高山吡啶（3）及其它们的立体选择性合成非对映异构体（分别为2和4）是从现成的4-羟基苯甲醛制得的。合成序列涉及布朗斯的烯丙基化和Et 2 Zn介导的非对映选择性炔基化反应为关键步骤。
• Diarylheptanoids from the Seeds of <i>Alpinia katsumadai</i> as Heat Shock Factor 1 Inducers
  作者：Joo-Won Nam、Ga-Young Kang、Ah-Reum Han、Dongho Lee、Yun-Sil Lee、Eun-Kyoung Seo

  DOI：10.1021/np200355n

  日期：2011.10.28

  Seven new diarylheptanoids, (-)-(R)-4 ''-hydroxyyashabushiketol (1), (3S,5S)-alpinikatin (2), katsumain C (3), 7-epi-katsumain C (4), ent-alpinnanin B (5), ent-alpinnanin A (6), and ent-calyxin H (8), were isolated from the EtOAc extract of the seeds of Alpinia katsumadai together with three known compounds, alpinnanin B (7), epicalyxin H (9), and calyxin H (10). Each isomer mixture of 3 and 4,5-7, and 8-10 was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (3 and 4, 5-7, 8-10) at 1 mu M increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 M. Compounds 1 and 2 did not affect the induction of HSF1 protein.