(2E,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-yl diethyl phosphate | 360042-90-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-yl diethyl phosphate
• 英文别名: [(2E,6E)-1,1-dideuterio-2,6-dimethyl-8-phenylmethoxyocta-2,6-dienyl] diethyl phosphate
• CAS: 360042-90-6
• 化学式: C₂₁H₃₃O₅P
• 分子量: 398.448
• InChiKey: WBEZSGPIFLDVKE-BCKFTWIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-yl diethyl phosphate 在 硼氘化锂 、 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2E,6E)-3,7-dimethyl[8,8,8-2H3]octa-2,6-dien-1-ol
  参考文献：
  名称：

  Stereochemical disposition of the geminal dimethyl groups in the enzymatic cyclization of geranyl diphosphate to (+)-bornyl diphosphate by recombinant (+)-bornyl diphosphate synthase from Salvia officinalis

  摘要：

  Regiospecifically deuterated geranyl diphosphate, in concert with NMR spectrometry, was employed to demonstrate that the trans-methyl group (C8) of geranyl diphosphate becomes the C9 carbon of (+)-bornyl diphosphate (geminal methyl syn to the diphosphate moiety) and that the cis-methyl group (C9) becomes the C8 (geminal methyl anti to the diphosphate). The syntheses of the relevant substrates and products, with accompanying spectrometric data are provided. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00451-3
• 作为产物：
  描述：

  (E)-4-methyl-6-(phenylmethoxy)-4-hexenal 在 吡啶 、 三氯化铝 、 lithium aluminium deuteride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2E,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-yl diethyl phosphate
  参考文献：
  名称：

  Stereochemical disposition of the geminal dimethyl groups in the enzymatic cyclization of geranyl diphosphate to (+)-bornyl diphosphate by recombinant (+)-bornyl diphosphate synthase from Salvia officinalis

  摘要：

  Regiospecifically deuterated geranyl diphosphate, in concert with NMR spectrometry, was employed to demonstrate that the trans-methyl group (C8) of geranyl diphosphate becomes the C9 carbon of (+)-bornyl diphosphate (geminal methyl syn to the diphosphate moiety) and that the cis-methyl group (C9) becomes the C8 (geminal methyl anti to the diphosphate). The syntheses of the relevant substrates and products, with accompanying spectrometric data are provided. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00451-3

文献信息

• Stereochemical disposition of the geminal dimethyl groups in the enzymatic cyclization of geranyl diphosphate to (+)-bornyl diphosphate by recombinant (+)-bornyl diphosphate synthase from Salvia officinalis
  作者：Mitchell L Wise、Hyung-Jung Pyun、Greg Helms、Bryce Assink、Robert M Coates、Rodney B Croteau

  DOI：10.1016/s0040-4020(01)00451-3

  日期：2001.6

  Regiospecifically deuterated geranyl diphosphate, in concert with NMR spectrometry, was employed to demonstrate that the trans-methyl group (C8) of geranyl diphosphate becomes the C9 carbon of (+)-bornyl diphosphate (geminal methyl syn to the diphosphate moiety) and that the cis-methyl group (C9) becomes the C8 (geminal methyl anti to the diphosphate). The syntheses of the relevant substrates and products, with accompanying spectrometric data are provided. (C) 2001 Elsevier Science Ltd. All rights reserved.