(2E,6Z)-(8,8,8-2H3)-3,7-dimethyl-2,6-octadien-1-ol | 360043-04-5

• 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: (2E,6Z)-(8,8,8-2H3)-3,7-dimethyl-2,6-octadien-1-ol
• 英文别名: (2E,6Z)-(8,8,8-2H3)-3,7-dimethyl-2,6-octadienoate；(2E,6Z)-8,8,8-trideuterio-3,7-dimethylocta-2,6-dien-1-ol
• CAS: 360043-04-5
• 化学式: C₁₀H₁₈O
• 分子量: 157.228
• InChiKey: GLZPCOQZEFWAFX-HEDCVWJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2E,6Z)-(8,8,8-2H3)-3,7-dimethyl-2,6-octadien-1-ol 在 2,4,6-三甲基吡啶 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 甲基磺酰氯 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 diammonium hydrogen (2E,6Z)-(8,8,8-2H3)-3,7-dimethyl-2,6-octadien-1-yl diphosphate
  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：

  (2Z,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,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

文献信息

• Syn Stereochemistry of Cyclic Ether Formation in 1,8-Cineole Biosynthesis Catalyzed by Recombinant Synthase from <i>Salvia officinalis</i>
  作者：Mitchell L. Wise、Marek Urbansky、Gregory L. Helms、Robert M. Coates、Rodney Croteau

  DOI：10.1021/ja0265714

  日期：2002.7.1

  Regiospecifically labeled geranyl diphosphates ((2E,6E)-[1,1,8,8,8-(2)H(5)]- and (2E,6Z)-[1,1,9,9,9-(2)H(5)]-GDP) and D(2)O incorporation, in concert with NMR spectrometry, were employed to demonstrate a unique intramolecular syn-facial protonation-cyclization mechanism of action of 1,8-cineole synthase.
• IZUMI, SHUNSUKE;AIHARA, MIE;HIRAGA, YOSHIKAZU;HIRATA, TOSHIFUMI;SUGA, TAK+, J. LABELL. COMPOUNDS AND RADIOPHARM., 29,(1991) N, C. 591-597
  作者：IZUMI, SHUNSUKE、AIHARA, MIE、HIRAGA, YOSHIKAZU、HIRATA, TOSHIFUMI、SUGA, TAK+

  DOI：——

  日期：——