1-(3,4-dimethoxyphenyl)-3-(trimethylsilyloxy)buta-1,3-diene | 748157-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dimethoxyphenyl)-3-(trimethylsilyloxy)buta-1,3-diene
• 英文别名: [(3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-2-yl]oxy-trimethylsilane
• CAS: 748157-67-7
• 化学式: C₁₅H₂₂O₃Si
• 分子量: 278.423
• InChiKey: PPSFYHBEXGGSLO-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-3-(trimethylsilyloxy)buta-1,3-diene 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (E)-4-(3,4-Dimethoxy-phenyl)-1-piperidin-2-yl-but-3-en-2-one; compound with trifluoro-acetic acid
  参考文献：
  名称：

  One-Pot Preparation of Quinolizidin-2-one and Indolizidin-7-one Ring Systems. Concise Total Syntheses of (.+-.)-Myrtine, (.+-.)-Lasubine II, and (-)-Indolizidine 223AB

  摘要：

  highly efficient approach to the quinolizidine alkaloids (+/-)-myrtine (4) and (+/-)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/17 is based on the addition of 2-((trimethylsilyl)oxy) 1,3-dienes 2a,b and 2c to cyclic N-acyliminium ions 10 and 15, respectively. It encompasses five chemical transformations in the same pot yielding the axially oriented substituent at C-4 and C-5 as the major product in the quinolizidin-2-one and indolizidin-7-one systems, respectively. The thermodynamically more stable isomers 12b and 17 were obtained after basic treatment.

  DOI：

  10.1021/jo00108a040
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 1-(3,4-dimethoxyphenyl)-3-(trimethylsilyloxy)buta-1,3-diene
  参考文献：
  名称：

  新型苯并[ a ]喹诺唑烷类似物通过截瘫和凋亡诱导癌细胞死亡

  摘要：

  截瘫是非凋亡性细胞死亡，其特征在于大量内质网（ER）或线粒体来源的液泡。与依赖凋亡的抗癌药物相比，诱发上pt裂可为化疗耐药性肿瘤的治疗提供显着优势。由于某些天然生物碱可诱导麻痹性细胞死亡，因此合成了一系列新的苯并[ a ]喹诺唑烷衍生物，并对其抗增殖活性和诱导细胞质空泡的能力进行了分析。结构优化导致了强效化合物22b的鉴定，该化合物在体内外抑制癌细胞的增殖，并极大地促进了类麻痹样细胞的死亡并诱导了caspase依赖性细胞凋亡。进一步调查发现22b介导的空泡作用源自持续的内质网应激和LC3B的上调。因此，由苯并[ a ]喹啉嗪衍生物诱导的截瘫代表了癌症化学疗法的另一种策略。

  DOI：

  10.1021/acs.jmedchem.6b00484

文献信息

• Synthesis of 5-Aryl-1,4-naphthoquinone and 1-Aryl-9,10-anthraquinone Derivatives by Cycloaddition of 1-(Dimethoxyphenyl)-3-trimethylsiloxy-1,3-butadienes to 1,4-Benzoquinones and 1,4-Naphthoquinones
  作者：I. V. Nechepurenko、E. E. Shul'ts、G. A. Tolstikov

  DOI：10.1023/b:rujo.0000010560.88282.d3

  日期：2003.10

  The Diels-Alder reaction of new 1-(3,4-dimethoxyphenyl)- or 1-(2,4-dimethoxyphenyl)-2-R-3-tri-methylsiloxy-1,3-butadienes with 2,5- and 2,6-dibromo-, and 2-bromo-6-methyl-1,4-benzoquinones regio- selectively yields substituted 7-hydroxy-5-(dimethoxyphenyl)-1,4-naphthoquinones. By cycloaddition of the siloxydienes to naphthoquinone, bromonaphthoquinone, and juglone the corresponding substituted 3-hydroxy-1- (dimethoxyphenyl)-9,10-anthraquinones or their 4,4a-dihydro or 1,1a,4,4a-tetrahydro derivatives were obtained.
• Novel Benzo[<i>a</i>]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis
  作者：Hongbo Zheng、Yiwen Dong、Lin Li、Bin Sun、Lei Liu、Huiqing Yuan、Hongxiang Lou

  DOI：10.1021/acs.jmedchem.6b00484

  日期：2016.5.26

  massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability

  截瘫是非凋亡性细胞死亡，其特征在于大量内质网（ER）或线粒体来源的液泡。与依赖凋亡的抗癌药物相比，诱发上pt裂可为化疗耐药性肿瘤的治疗提供显着优势。由于某些天然生物碱可诱导麻痹性细胞死亡，因此合成了一系列新的苯并[ a ]喹诺唑烷衍生物，并对其抗增殖活性和诱导细胞质空泡的能力进行了分析。结构优化导致了强效化合物22b的鉴定，该化合物在体内外抑制癌细胞的增殖，并极大地促进了类麻痹样细胞的死亡并诱导了caspase依赖性细胞凋亡。进一步调查发现22b介导的空泡作用源自持续的内质网应激和LC3B的上调。因此，由苯并[ a ]喹啉嗪衍生物诱导的截瘫代表了癌症化学疗法的另一种策略。
• One-Pot Preparation of Quinolizidin-2-one and Indolizidin-7-one Ring Systems. Concise Total Syntheses of (.+-.)-Myrtine, (.+-.)-Lasubine II, and (-)-Indolizidine 223AB
  作者：Ronaldo A. Pilli、Luiz Carlos Dias、Adriano O. Maldaner

  DOI：10.1021/jo00108a040

  日期：1995.2

  highly efficient approach to the quinolizidine alkaloids (+/-)-myrtine (4) and (+/-)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/17 is based on the addition of 2-((trimethylsilyl)oxy) 1,3-dienes 2a,b and 2c to cyclic N-acyliminium ions 10 and 15, respectively. It encompasses five chemical transformations in the same pot yielding the axially oriented substituent at C-4 and C-5 as the major product in the quinolizidin-2-one and indolizidin-7-one systems, respectively. The thermodynamically more stable isomers 12b and 17 were obtained after basic treatment.