(3R)-3,7-dimethyloct-6-en-1-yl methanesulfonate | 119591-57-0

• 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: (3R)-3,7-dimethyloct-6-en-1-yl methanesulfonate
• 英文别名: [(3R)-3,7-dimethyloct-6-enyl] methanesulfonate
• CAS: 119591-57-0
• 化学式: C₁₁H₂₂O₃S
• 分子量: 234.36
• InChiKey: REOTWSUDNJILTP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3,7-dimethyloct-6-en-1-yl methanesulfonate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (S)-2,6-dimethyloct-2-ene
  参考文献：
  名称：

  从海藻中分离出来的一种有效的脂质过氧化抑制剂，Martefragin A的首次全合成

  摘要：

  从海藻中分离出来的一种有效的脂质过氧化抑制剂，Martafragin A的首次完整合成已完成，并确定了两个立体生成中心的绝对构型。合成的martefragin A，其立体异构体和某些类似物使用大鼠肝微粒体对脂质过氧化具有较强的抑制活性。

  DOI：

  10.1016/s0040-4039(98)01228-3
• 作为产物：
  描述：

  (R)-(+)-香茅酸 在 lithium aluminium tetrahydride 作用下， 生成 (3R)-3,7-dimethyloct-6-en-1-yl methanesulfonate
  参考文献：
  名称：

  Naoshima, Yoshinobu; Hayashi, Daijiro; Ochi, Masato, Agricultural and Biological Chemistry, 1988, vol. 52, # 6, p. 1605 - 1606

  摘要：

  DOI：

文献信息

• Rhodium(iii)-catalyzed allylic C–H bond amination. Synthesis of cyclic amines from ω-unsaturated N-sulfonylamines
  作者：Thomas Cochet、Véronique Bellosta、Didier Roche、Jean-Yves Ortholand、Alfred Greiner、Janine Cossy

  DOI：10.1039/c2cc36067e

  日期：——

  For the first time, intramolecular allylic amination was conducted using rhodium(III) according to an "inner-sphere" type mechanism with amines activated by only one electron-withdrawing group. The activation of C(sp(3))-H bonds was chemoselective and allows the access to a variety of substituted cyclic amines such as pyrrolidines and piperidines.

  第一次，根据“内球”型机理，使用铑（III）用仅由一个吸电子基团活化的胺进行了分子内烯丙基胺化反应。C（sp（3））-H键的激活是化学选择性的，并允许访问各种取代的环胺，如吡咯烷和哌啶。
• 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.
• 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).
• TAKANO, SEHJITI;OGASAVARA, KUNIO;SIBATA, TOSIXIRO
  作者：TAKANO, SEHJITI、OGASAVARA, KUNIO、SIBATA, TOSIXIRO

  DOI：——

  日期：——