(3S)-3-(1-hydroxyallyloxy)hex-5-en-1-ol | 1193252-16-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S)-3-(1-hydroxyallyloxy)hex-5-en-1-ol
• 英文别名: (S)-1-(2-hydroxyethyl)but-3-enyl acrylate；(3S)-1-hydroxyhex-5-en-3-yl acrylate；[(3S)-1-hydroxyhex-5-en-3-yl] prop-2-enoate
• CAS: 1193252-16-2
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: TZFJXJVNKGMTFH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-(1-hydroxyallyloxy)hex-5-en-1-ol 在 Grubbs catalyst first generation 、 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (R,E)-6-(6-(naphthalen-2-yl)-4-oxohex-2-enyl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells

  摘要：

  Rugulactone and its analogues were synthesized following Horners-Wadsworth-Emmons and ring-closing metathesis as the key reactions. A library of new rugulactone analogues were designed, synthesized and evaluated for their anticancer activity in breast cancer cells. All analogues have shown anti-proliferative activity, while some of them exhibited significant cytotoxicity. In assays related to cell-cycle distribution, these conjugates induced G1 cell-cycle arrest in MDA-MB-231 cells. The cell cycle arrest nature was further confirmed by examining the effect on Cyclin E and Cdk2 proteins that acts at G1-S phase transition. Immunocytochemistry assay revealed that these compounds inhibited nuclear translocation of NF-kappa B protein, thereby activation of NF-kappa B was inhibited. The expression of NF-kappa B target genes such as Cyclin D1 and Bcl-xL were severely affected. Apart from acting on NF-kappa B, these compounds also regulate class I Histone deacetylase proteins such as (HDAC-3 and 8) that have a crucial and regulatory role in cellproliferation. Simultaneously, the apoptotic inducing nature of these compounds was confirmed by activation of PARP protein, a protein that plays a key role in DNA damage and repair pathways. Among all compounds of this series 3g is the most potent compound and can be used for further studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.030
• 作为产物：
  描述：

  (S)-1-((4-methoxybenzyl)oxy)hex-5-en-3-ol 在 水 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (3S)-3-(1-hydroxyallyloxy)hex-5-en-1-ol
  参考文献：
  名称：

  分离与细胞毒性Cryptolactones A的全合成1，A 2，B 1和B 2：α，从β不饱和δ内酯Cryptomyzus藻。蚜

  摘要：

  从Cryptomyzus sp。分离到α，β-不饱和δ-内酯的隐内酯A 1，A 2，B 1和B 2。蚜。通过1-D和2-D NMR光谱以及CI-HRMS建立结构。它们的绝对构型是用Kusumi-Mosher方法结合不对称总合成法确定的。合成是通过Mukaiyama aldol反应和烯烃复分解完成的，烯烃复分解利用第二代Grubbs催化剂进行关键步骤。这些化合物对人早幼粒细胞白血病HL-60细胞具有细胞毒活性，IC 50值为0.97–5.3μM。

  DOI：

  10.1021/np500542x

文献信息

• A Concise and Efficient Synthesis of (5R,7S)-Kurzilactone and Its (5S,7R)-Enantiomer by the Mukaiyama Aldol Reaction
  作者：Gowravaram Sabitha、Peddabuddi Gopal、C. Reddy、Jhillu Yadav

  DOI：10.1055/s-0029-1216936

  日期：2009.10

  Natural kurzilactone (5R,7S) and its (5S,7R)-enantiomer were synthesized by a convergent approach using a diastereoselective Mukaiyama aldol reaction to construct the anti diol unit. Finally, a ring-closing metathesis reaction led to the target molecule. kurzilactone - Mukaiyama reaction - aldol reaction - ring closure - metathesis

  使用非对映选择性Mukaiyama aldol反应通过收敛方法合成天然kurzilactone（5 R，7 S）及其（5 S，7 R）-对映异构体，以构建抗二醇单元。最后，闭环复分解反应产生了靶分子。 kurzilactone-Mukaiyama反应-aldol反应-闭环-复分解
• Isolation and Total Syntheses of Cytotoxic Cryptolactones A₁, A₂, B₁, and B₂: α,β-Unsaturated δ-Lactones from a <i>Cryptomyzus</i> sp. Aphid
  作者：Mitsuyo Horikawa、Makoto Inai、Yuki Oguri、Eri Kuroda、Masami Tanaka、Shinya Suzuki、Takuya Ito、Shigeru Takahashi、Hiroto Kaku、Tetsuto Tsunoda

  DOI：10.1021/np500542x

  日期：2014.11.26

  The cryptolactones A1, A2, B1, and B2, which are α,β-unsaturated δ-lactones, were isolated from a Cryptomyzus sp. aphid. The structures were established by 1-D and 2-D NMR spectra and CI-HRMS. Their absolute configurations were determined with the Kusumi–Mosher method, combined with asymmetric total syntheses. The syntheses were accomplished with the Mukaiyama aldol reaction and olefin metathesis,

  从Cryptomyzus sp。分离到α，β-不饱和δ-内酯的隐内酯A 1，A 2，B 1和B 2。蚜。通过1-D和2-D NMR光谱以及CI-HRMS建立结构。它们的绝对构型是用Kusumi-Mosher方法结合不对称总合成法确定的。合成是通过Mukaiyama aldol反应和烯烃复分解完成的，烯烃复分解利用第二代Grubbs催化剂进行关键步骤。这些化合物对人早幼粒细胞白血病HL-60细胞具有细胞毒活性，IC 50值为0.97–5.3μM。
• First total syntheses and absolute configuration of rugulactone and 6(R)-(4′-oxopent-2′-enyl)-5,6-dihydro-2H-pyran-2-one
  作者：Debendra K. Mohapatra、Pragna P. Das、D. Sai Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2009.08.028

  日期：2009.10

  The first efficient total syntheses of rugulactone and 6(R)-(4'-oxopent-2'-enyl)-5,6-dihydro-2H-pyran-2-one have been achieved in six steps with 51% and 48% overall yield, respectively. The key steps are Jacobsen's hydrolytic kinetic resolution (HKR), Horner-Wadsworth-Emmons (HWE) homologation, and ring-closing metathesis reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells
  作者：Debendra K. Mohapatra、D. Sai Reddy、M. Janaki Ramaiah、Sowjanya Ghosh、Vikram Pothula、Swetha Lunavath、Shine Thomas、S.N.C.V.L. Pushpa Valli、Manika Pal Bhadra、Jhillu S. Yadav

  DOI：10.1016/j.bmcl.2014.01.030

  日期：2014.3

  Rugulactone and its analogues were synthesized following Horners-Wadsworth-Emmons and ring-closing metathesis as the key reactions. A library of new rugulactone analogues were designed, synthesized and evaluated for their anticancer activity in breast cancer cells. All analogues have shown anti-proliferative activity, while some of them exhibited significant cytotoxicity. In assays related to cell-cycle distribution, these conjugates induced G1 cell-cycle arrest in MDA-MB-231 cells. The cell cycle arrest nature was further confirmed by examining the effect on Cyclin E and Cdk2 proteins that acts at G1-S phase transition. Immunocytochemistry assay revealed that these compounds inhibited nuclear translocation of NF-kappa B protein, thereby activation of NF-kappa B was inhibited. The expression of NF-kappa B target genes such as Cyclin D1 and Bcl-xL were severely affected. Apart from acting on NF-kappa B, these compounds also regulate class I Histone deacetylase proteins such as (HDAC-3 and 8) that have a crucial and regulatory role in cellproliferation. Simultaneously, the apoptotic inducing nature of these compounds was confirmed by activation of PARP protein, a protein that plays a key role in DNA damage and repair pathways. Among all compounds of this series 3g is the most potent compound and can be used for further studies. (C) 2014 Elsevier Ltd. All rights reserved.