4-ethenyl-3,6-dihydro-2H-pyran | 1356254-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-ethenyl-3,6-dihydro-2H-pyran
• CAS: 1356254-91-5
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: JQMIPJOZLAFWHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-ethenyl-3,6-dihydro-2H-pyran 、 4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 苯 为溶剂， 反应 14.0h， 以22%的产率得到1-methyl-7,9-dihydro-6H-[1]benzofuro[7,6-h]isochromene-10,11-dione
  参考文献：
  名称：

  Antiandrogenic, Maspin Induction, and Antiprostate Cancer Activities of Tanshinone IIA and Its Novel Derivatives with Modification in Ring A

  摘要：

  Expression of metastatic suppressor maspin is lost in advanced prostate cancer. Clinically relevant mutations in androgen receptor (AR) convert antiandrogens into AR agonists, promoting prostate tumor growth. We discovered tanshinone IIA (TS-IIA) is a potent antagonist of mutated ARs and induces maspin expression through AR. TS-IIA suppressed AR expression and induced apoptosis in LNCaP cells. Syntheses of TS-IIA derivatives (1-9) revealed that the 4,4-dimethyl group at ring A is important for TS-IIA's antiandrogenic and maspin induction activities.

  DOI：

  10.1021/jm2015292
• 作为产物：
  描述：

  4-vinyltetrahydro-2H-pyran-4-ol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以63%的产率得到4-ethenyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Antiandrogenic, Maspin Induction, and Antiprostate Cancer Activities of Tanshinone IIA and Its Novel Derivatives with Modification in Ring A

  摘要：

  Expression of metastatic suppressor maspin is lost in advanced prostate cancer. Clinically relevant mutations in androgen receptor (AR) convert antiandrogens into AR agonists, promoting prostate tumor growth. We discovered tanshinone IIA (TS-IIA) is a potent antagonist of mutated ARs and induces maspin expression through AR. TS-IIA suppressed AR expression and induced apoptosis in LNCaP cells. Syntheses of TS-IIA derivatives (1-9) revealed that the 4,4-dimethyl group at ring A is important for TS-IIA's antiandrogenic and maspin induction activities.

  DOI：

  10.1021/jm2015292

文献信息

• Three-component carboformylation: α-quaternary aldehyde synthesis <i>via</i> Co(<scp>iii</scp>)-catalysed sequential C–H bond addition to dienes and acetic formic anhydride
  作者：Joseph P. Tassone、Jihyeon Yeo、Jonathan A. Ellman

  DOI：10.1039/d2sc05599f

  日期：——

  containing diverse functionality can be employed in this reaction, affording complex α-quaternary aldehydes that would not be accessible via hydroformylation approaches. Mechanistic investigations, including control reactions and deuterium labeling studies, establish a catalytic cycle that accounts for formyl group introduction with an uncommon 1,3-addition selectivity to the conjugated diene. Investigations

  所有碳 α-季醛都是通过Co( III ) 催化的顺序 C-H 键加成到二烯和乙酸甲酸酐制备的，代表了分子间碳甲酰化的罕见例子。在该反应中可以使用多种包含不同官能度的内部取代二烯，提供复杂的 α-季醛，而这些醛无法通过加氢甲酰化方法。包括控制反应和氘标记研究在内的机理研究建立了一个催化循环，该循环解释了甲酰基团的引入以及对共轭二烯的罕见 1,3-加成选择性。还对独特有效的添加剂 Proton Sponge® 的作用进行了研究，从而通过核磁共振光谱在低温下观察到假定的中间体 Co( I ) 四甲基富烯络合物。醛产物的合成效用通过各种转化得到证明，包括脯氨酸催化的不对称羟醛加成、还原胺化和使用叔丁亚磺酰胺技术的胺的不对称合成。
• Antiandrogenic, Maspin Induction, and Antiprostate Cancer Activities of Tanshinone IIA and Its Novel Derivatives with Modification in Ring A
  作者：Weiguo Liu、Jinming Zhou、Guoyan Geng、Qingwen Shi、Francoise Sauriol、Jian Hui Wu

  DOI：10.1021/jm2015292

  日期：2012.1.26

  Expression of metastatic suppressor maspin is lost in advanced prostate cancer. Clinically relevant mutations in androgen receptor (AR) convert antiandrogens into AR agonists, promoting prostate tumor growth. We discovered tanshinone IIA (TS-IIA) is a potent antagonist of mutated ARs and induces maspin expression through AR. TS-IIA suppressed AR expression and induced apoptosis in LNCaP cells. Syntheses of TS-IIA derivatives (1-9) revealed that the 4,4-dimethyl group at ring A is important for TS-IIA's antiandrogenic and maspin induction activities.