(R,2E,4E)-6-((tert-butyldimethylsilyloxy)methyl)octa-2,4-dien-1-ol | 1501971-70-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R,2E,4E)-6-((tert-butyldimethylsilyloxy)methyl)octa-2,4-dien-1-ol
• 英文别名: (2E,4E,6R)-6-(tert-butyldimethylsilyloxymethyl)octa-2,4-dien-1-ol
• CAS: 1501971-70-5
• 化学式: C₁₅H₃₀O₂Si
• 分子量: 270.488
• InChiKey: ZKNCDHIORKLWHF-WKHONTLPSA-N

物化性质

• 沸点：
  329.6±30.0 °C(predicted)
• 密度：
  0.891±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R,2E,4E)-6-((tert-butyldimethylsilyloxy)methyl)octa-2,4-dien-1-ol 在 草酰氯 、 sodium hydride 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 torrubiellone B
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d
• 作为产物：
  描述：

  (R)-2-((tert-butyldimethylsilyloxy)methyl)butan-1-ol 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R,2E,4E)-6-((tert-butyldimethylsilyloxy)methyl)octa-2,4-dien-1-ol
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d

文献信息

• Synthesis and Antibacterial Activity of Four Stereoisomers of the Spider-Pathogenic Fungus Metabolite Torrubiellone D
  作者：Sebastian Bruckner、Ursula Bilitewski、Rainer Schobert

  DOI：10.1021/acs.orglett.6b00245

  日期：2016.3.4

  Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from l-tyrosine or d-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.

  蜘蛛致病性真菌代谢产物托瑞比隆D的四种立体异构体以1-酪氨酸或d-酪氨酸为起始原料，首次以10％的总收率合成。3-癸三烯酰基侧链通过（E）-选择性HWE和Wittig烯化反应组装并连接。它们对药物敏感的大肠杆菌菌株的抗生素活性差异很大。