(E)-3,7,11-trimethyldodeca-2,10-dien-1-ol | 127306-25-6

• 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: (E)-3,7,11-trimethyldodeca-2,10-dien-1-ol
• 英文别名: (7S)-trans-6,7-dihydrofarnesol；(2E,7S)-3,7,11-trimethyldodeca-2,10-dien-1-ol
• CAS: 127306-25-6
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: XOTVPLZGIIGSKR-XDPMZMSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3,7,11-trimethyldodeca-2,10-dien-1-ol 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.67h， 以100%的产率得到(3RS,7S)-3,7,11-trimethyl-10-dodecen-1-ol
  参考文献：
  名称：

  Structure–activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines

  摘要：

  To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.035
• 作为产物：
  描述：

  methyl (S,Z)-7,11-dimethyl-3-(tosyloxy)dodeca-2,10-dienoate 在 bis-triphenylphosphine-palladium(II) chloride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.92h， 生成 (E)-3,7,11-trimethyldodeca-2,10-dien-1-ol
  参考文献：
  名称：

  Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali

  摘要：

  The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.080

文献信息

• Trichodiene Synthase. Stereochemical Studies of the Cryptic Allylic Diphosphate Isomerase Activity Using an Anomalous Substrate
  作者：David E. Cane、Guohan Yang

  DOI：10.1021/jo00098a046

  日期：1994.9

  Incubation of (7S)-6,7-dihydrofarnesyl diphosphate with trichodiene synthase gave, as previously described, a mixture consisting of 80% dihydrofarnesene isomers 6-8 accompanied by 6% trans- 6,7-dihydrofarnesol (10) and 13% 6,7-dihydronerolidol (9). The latter product has now been shown to be (3S,7S)-6,7-dihydronerolidol [(3S,7S)-9] by direct comparison with synthetic (3S,7S)-6,7-dihydronerolidol and (3RS,7S)-6,7-dihydronerolidol using chiral capillary gas chromatography. The observed formation of (3S,7S)-9 can be accounted for by backside attack of water on an allylic cation-pyrophosphate anion pair generated by syn allylic rearrangement of dihydrofarnesyl diphosphate (5) and ionization of the resulting (3R,7S)-6,7-dihydronerolidyl diphosphate (14). These results provide further support for the proposed isomerization of farnesyl diphosphate (1) to (3R)-nerolidyl diphosphate (3) in the enzymatic formation trichodiene (2).
• Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali
  作者：Kanako Kaihara、Toyomi Kotaki、Hideharu Numata、Yasufumi Ohfune、Tetsuro Shinada

  DOI：10.1016/j.tet.2011.10.080

  日期：2012.1

  The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Structure–activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines
  作者：Yoshitomo Suhara、Akimori Wada、Yoji Tachibana、Masato Watanabe、Kanae Nakamura、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2010.03.035

  日期：2010.5

  To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes. (c) 2010 Elsevier Ltd. All rights reserved.