(4aS,5S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone | 120108-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,5S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
• 英文别名: (+/-)-(4aR,5R,8S,8aR)-8-(tert-Butyldimethylsilyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione；(4aS,5S,8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2,5,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
• CAS: 120108-93-2
• 化学式: C₁₉H₃₀O₃Si
• 分子量: 334.531
• InChiKey: YONUPHDWJUOAPQ-GCUGWZBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙醛二乙基乙缩醛 、 (4aS,5S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 在 正丁基锂 作用下， 生成 (4R,4aS,5R,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(3,3-diethoxy-prop-1-ynyl)-4-hydroxy-3,4a,8-trimethyl-4a,5,8,8a-tetrahydro-4H-naphthalen-1-one
  参考文献：
  名称：

  Acetylide additions to enediones. Regioselectivity based on stereoelectronic control

  摘要：

  DOI：

  10.1021/jo00217a055
• 作为产物：
  描述：

  2,6-二甲基-2,5-环己二烯-1,4-二酮 、 (1E,3E)-1-(t-butyldimethylsilyloxy)penta-1,3-diene 反应 168.0h， 以73%的产率得到(4aS,5S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  摘要：

  Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels-Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene.

  DOI：

  10.1071/ch00027

文献信息

• Molecular aggregation and its applicability to synthesis. The Diels-Alder reaction
  作者：Tambra Dunams、William Hoekstra、Michael Pentaleri、Dennis Liotta

  DOI：10.1016/s0040-4039(00)82104-8

  日期：1988.1