(E)-4,8-dimethylnona-3,7-dienyl methanesulfonate | 118495-32-2

• 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)-4,8-dimethylnona-3,7-dienyl methanesulfonate
• 英文别名: homogeraniol mesylate；(E)-4,8-dimethylnona-3,7-dien-1-yl methanesulfonate；[(3E)-4,8-dimethylnona-3,7-dienyl] methanesulfonate
• CAS: 118495-32-2
• 化学式: C₁₂H₂₂O₃S
• 分子量: 246.371
• InChiKey: MTGOBASRAJDKEO-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (E)-4,8-dimethylnona-3,7-dienyl methanesulfonate 在 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以64%的产率得到homogeranyl bromide
  参考文献：
  名称：

  摘要：

  The reproductive behavior of the stink bug Chlorochroa sayi was studied in the laboratory. There was a sexual maturation period of about 10 days before bugs began mating. Sexually mature adult bugs engaged in courtship consisting of antennation and head-butting of the female by the male, before the female adopted a receptive posture and copulation occurred. Both sexes mated multiple times during their life-spans, with the mean duration of copulations of virgin bugs (42.3 +/- 19.6 min) and experienced bugs (37.3 +/- 28.4 min) being similar. Most matings were initiated in the late afternoon or evening, when pheromone production by males was greatest. Males transferred sperm and nutrients constituting about 17% of their body weight to females during mating. Three male-specific components, methyl geranate, methyl citronellate, and methyl (E)-6-2,3-dihydrofarnesoate in a ratio of 100 : 0.45 : 1.6, were first detected in volatiles collected from male bugs on green beans about 9-12 days after the final molt to the adult stage. In vertical Y-tube bioassays, females were attracted to odors from mature male bugs, and to a blend of the three male-produced components. Low numbers of females also were attracted in field trials with the three-component blend. The relatively weak attraction may be a result of other, as yet unknown cues being required in addition to the pheromone, such as visual or substrate-borne vibrational cues.

  DOI：

  10.1023/a:1010368013235
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 sodium hydroxide 、 (Si₁)2BH 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 生成 (E)-4,8-dimethylnona-3,7-dienyl methanesulfonate
  参考文献：
  名称：

  Synthesis of Pyrrolostatin and Its Analogues

  摘要：

  DOI：

  10.1021/jo990666f

文献信息

• Recombinant Squalene Synthase. A Mechanism for the Rearrangement of Presqualene Diphosphate to Squalene
  作者：Brian S. J. Blagg、Michael B. Jarstfer、Daniel H. Rogers、C. Dale Poulter

  DOI：10.1021/ja020411a

  日期：2002.7.1

  of squalene; and rillingol (ROH), a cyclopropylcarbinyl alcohol formed by addition of water to the tertiary cyclopropylcarbinyl cation previously proposed as an intermediate in the rearrangement of PSPP to SQ (Poulter, C. D. Acc. Chem. Res. 1990, 23, 70-77). The structure and absolute stereochemistry of the tertiary cyclopropylcarbinyl alcohol were established by synthesis using two independent routes

  角鲨烯合酶 (SQase) 催化两个分子的法呢基二磷酸 (FPP) 缩合形成二磷酸前角鲨烯 (PSPP)，随后 PSPP 重排和 NADPH 依赖性还原为角鲨烯 (SQ)。这些反应是胆固醇生物合成的第一步。当重组 SQase 在二氢 NADPH（NADPH3，一种在烟酰胺环中缺少 5,6-双键的非反应性类似物）存在下与 FPP 一起温育时，形成了三种产物：脱氢角鲨烯 (DSQ)，一种八氢番茄红素的 C30 类似物；10(S)-羟基角鲨烯 (HSQ)，角鲨烯的羟基类似物；和 rillingol (ROH)，一种环丙基甲醇，通过将水添加到叔环丙基甲醇阳离子中形成，先前提出作为 PSPP 重排为 SQ 的中间体 (Poulter, CD Acc. Chem. Res. 1990, 23, 70-77)。叔环丙基甲醇的结构和绝对立体化学是通过使用两条独立的路线合成建立的。从酶催化反应中分离 ROH
• Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates
  作者：Robert A. Matthiesen、Veronica S. Wills、Joseph I. Metzger、Sarah A. Holstein、David F. Wiemer

  DOI：10.1021/acs.joc.6b01693

  日期：2016.10.7

  Isoprenoid-substituted bisphosphonates are known to serve as inhibitors of the enzyme geranylgeranyl diphosphate synthase, and their activity can be highly sensitive to olefin stereochemistry. A mixture of homogeranyl and homoneryl triazole bisphosphonates has previously demonstrated potent activity, and thus stereocontrolled syntheses of the individual isomers have been developed.
• Synthesis of Pyrrolostatin and Its Analogues
  作者：Yumiko Fumoto、Tomomi Eguchi、Hidemitsu Uno、Noboru Ono

  DOI：10.1021/jo990666f

  日期：1999.8.1
• ——
  作者：Hsiao-Yung Ho、Jocelyn G. Millar

  DOI：10.1023/a:1010368013235

  日期：——

  The reproductive behavior of the stink bug Chlorochroa sayi was studied in the laboratory. There was a sexual maturation period of about 10 days before bugs began mating. Sexually mature adult bugs engaged in courtship consisting of antennation and head-butting of the female by the male, before the female adopted a receptive posture and copulation occurred. Both sexes mated multiple times during their life-spans, with the mean duration of copulations of virgin bugs (42.3 +/- 19.6 min) and experienced bugs (37.3 +/- 28.4 min) being similar. Most matings were initiated in the late afternoon or evening, when pheromone production by males was greatest. Males transferred sperm and nutrients constituting about 17% of their body weight to females during mating. Three male-specific components, methyl geranate, methyl citronellate, and methyl (E)-6-2,3-dihydrofarnesoate in a ratio of 100 : 0.45 : 1.6, were first detected in volatiles collected from male bugs on green beans about 9-12 days after the final molt to the adult stage. In vertical Y-tube bioassays, females were attracted to odors from mature male bugs, and to a blend of the three male-produced components. Low numbers of females also were attracted in field trials with the three-component blend. The relatively weak attraction may be a result of other, as yet unknown cues being required in addition to the pheromone, such as visual or substrate-borne vibrational cues.