(2Z,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-ol | 200397-73-5

• 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: (2Z,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-ol
• CAS: 200397-73-5
• 化学式: C₁₇H₂₄O₂
• 分子量: 262.36
• InChiKey: IQHBZERKKUKHDQ-IDOMMWMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (2Z,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-1-ol 在 吡啶 、 硼氘化锂 、 氨 、 lithium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2E,6Z)-(8,8,8-2H3)-3,7-dimethyl-2,6-octadien-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 三氯化铝 、 lithium aluminium deuteride 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.33h， 生成 (2Z,6E)-(1,1-2H2)-8-benzyloxy-2,6-dimethyl-2,6-octadien-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

文献信息

• Stereochemistry of the methyl→methylene elimination in the enzyme-catalysed cyclization of geranyl diphosphate to (4S)-limonene
  作者：Robert M. Coates、Charles S. Elmore、Robert M. Coates、Rodney B. Croteau、David C. Williams、Charles S. Elmore、Rodney B. Croteau、Hiromi Morimoto、Philip G. Williams

  DOI：10.1039/a704370h

  日期：——

  The cyclization of (R)-[9-2H1,3H1]geranyl diphosphate catalysed by a recombinant form of (4S)-limonene synthase from spearmint leaf (Mentha spicata) is terminated predominantly by re-facial, anti proton elimination at the cis methyl group, producing (4S, 8E)-[8-2H1,3H1]limonene.

  由重组形式的留兰香叶（Mentha spicata）(4S)-柠檬烯合成酶催化的(R)-[9-2H1,3H1]二磷酸香叶酯的环化主要通过顺式甲基上的反质子消除而终止，生成(4S, 8E)-[8-2H1,3H1]柠檬烯。