(E)-3,7,11-trimethyl-6,10-dodecadienoic acid | 80041-23-2

• 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)-3,7,11-trimethyl-6,10-dodecadienoic acid
• 英文别名: 3,7,11-trimethyl-6E,10-dodecadienoic acid；(E)-6-2,3-dihydrofarnesoic acid；2,3-dihydrofarnesic acid；(6E)-3,7,11-trimethyldodeca-6,10-dienoic acid
• CAS: 80041-23-2
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: HDAQPCUHLCPEHS-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3,7,11-trimethyl-6,10-dodecadienoic acid 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl (E)-6-2,3-dihydrofarnesoate
  参考文献：
  名称：

  Odinokov, V. N.; Kukovinets, O. S.; Sakharova, N. I., Russian Journal of Organic Chemistry, 1993, vol. 29, # 1.1, p. 24 - 30

  摘要：

  DOI：
• 作为产物：
  描述：

  香叶基溴 在 1,1-二溴乙烷 、 碘 甲醇 、 双氧水 、 碳酸氢钠 、 magnesium 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 33.5h， 生成 (E)-3,7,11-trimethyl-6,10-dodecadienoic acid
  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

文献信息

• Synthesis of (-)-LL-C10037α and Related Manumycin-Type Epoxyquinols
  作者：Peter Wipf、Yuntae Kim、Heike Jahn

  DOI：10.1055/s-1995-4141

  日期：1995.12

  Starting with N-allyloxycarbonyl-protected 2,5-dimethoxyaniline, hypervalent iodine oxidation protocols and selective enone epoxidation provides the Streptomyces metabolite LL-C10037α in nine steps and 7-10% overall yield. In an asymmetric variant of this strategy, (R,R)-pentane-2,4-diol is used as a chiral acetalization agent. The resulting semiquinone spiroacetal, due to an ortho-acylamino substituent that restricts the 1,3-dioxane ring conformation, undergoes face-selective epoxidation and is further functionalized to give (-)-LL-C10037α in 94% ee. These pathways represent the first syntheses of the highly functionalized mC7N core of the manumycins and have been further extended toward the preparation of analogs for SAR studies of this class of antitumor antibiotics. Manumycins inhibit the farnesylation of Ras-protein by PFTase (protein farnesyltransferase).

  以 N-烯丙氧基羰基保护的 2,5-二甲氧基苯胺为起点，通过高价碘氧化规程和选择性烯酮环氧化反应，九步即可得到链霉菌代谢物 LL-C10037δ，总收率为 7-10%。在这一策略的不对称变体中，(R,R)-戊烷-2,4-二醇被用作手性缩醛剂。由于正己胺基取代基限制了 1,3-二恶烷环的构象，由此产生的半醌螺缩醛进行了面选择性环氧化，并进一步官能化，得到了 (-)-LL-C10037 δ，ee 为 94%。这些方法首次合成了马诺霉素的高官能化 mC7N 核心，并进一步扩展到制备类似物，用于该类抗肿瘤抗生素的 SAR 研究。马努霉素能抑制 PFTase（蛋白法尼基转移酶）对 Ras 蛋白的法尼基化。
• Polyprenylcarboxylic acid amides useful for treating liver dysfunction
  申请人：Eisai Co., Ltd.

  公开号：US04456603A1

  公开（公告）日：1984-06-26

  Polyprenyl carboxylic acid amides of the formula ##STR1## process for their preparation and use thereof for treating liver dysfunction are disclosed.

  本发明揭示了公式##STR1## 的多萜基羧酸酰胺、其制备方法及其用于治疗肝功能障碍的用途。
• .alpha.,.beta.-Dihydropolyprenyl derivatives useful in treating hepatitis
  申请人：Eisai Co., Ltd.

  公开号：US04481217A1

  公开（公告）日：1984-11-06

  An .alpha.,.beta.-dihydropolyprenyl derivative having the formula (I): ##STR1## wherein X represents a group of --COOR.sub.1 or --CH.sub.2 OR.sub.2 in which R.sub.1 is the hydrogen atom or a lower alkyl group and R.sub.2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the .alpha.,.beta.-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.

  一种具有以下式子（I）的α，β-双氢聚戊烯衍生物：##STR1## 其中X代表一个--COOR.sub.1或--CH.sub.2 OR.sub.2的基团，其中R.sub.1是氢原子或较低的烷基基团，R.sub.2是氢原子或具有一到四个碳原子的脂肪族酰基基团；n是一个整数，范围从1到4。还公开了一种制备α，β-双氢聚戊烯衍生物的方法和包含其的治疗肝病的治疗剂。
• .alpha.,.beta.-Dihydropolyprenyl derivatives for treating hepatitis
  申请人：Eisai Co., Ltd.

  公开号：US04571408A1

  公开（公告）日：1986-02-18

  An .alpha.,.beta.-dihydropolyprenyl derivative having the formula (I): ##STR1## wherein X represents a group of --COOR.sub.1 or --CH.sub.2 OR.sub.2 in which R.sub.1 is the hydrogen atom or an alkyl group having one to four carbon atoms and R.sub.2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the .alpha.,.beta.-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.

  一种具有以下式子（I）的α，β-二氢聚戊烯衍生物：##STR1## 其中X代表一个基团，所述基团为--COOR.sub.1或--CH.sub.2 OR.sub.2，其中R.sub.1为氢原子或具有一到四个碳原子的烷基基团，R.sub.2为氢原子或具有一到四个碳原子的脂肪族酰基基团；n为1到4的整数。还公开了制备α，β-二氢聚戊烯衍生物的过程以及包含其的治疗肝病的治疗剂。
• Alpha,beta-dihydropolyprenyl derivatives for treating liver diseases
  申请人：Eisai Co., Ltd.

  公开号：EP0041235A2

  公开（公告）日：1981-12-09

  An α,β-dihydropolyprenyl derivative having the formula (I): wherein X represents a group of-COOR1 or-CH2OR2 in which R, is the hydrogen atom or a lower alkyl group and R2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the α,β-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.

  具有式(I)的α，β-二氢吡喃基衍生物： 其中 X 代表-COOR1 或-CH2OR2 的基团，其中 R 是氢原子或低级烷基，R2 是氢原子或具有 1 至 4 个碳原子的脂肪酰基；n 是 1 至 4 的整数。本发明还公开了一种制备α，β-二氢肾上腺烷基衍生物的工艺和一种治疗肝病的治疗剂。