2-甲基-7-十八碳烯 | 51050-50-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 2-甲基-7-十八碳烯
• 英文名称: trans-7,8-epoxy-2-methyloctadecane
• 英文别名: (E/Z)-2-methyl-7-octadecene；2-methyl-octadec-7-ene；2-Methyl-octadecen-(7)；2-Methyl-7-octadecen；7-Octadecene, 2-methyl-；2-methyloctadec-7-ene
• CAS: 51050-50-1
• 化学式: C₁₉H₃₈
• 分子量: 266.511
• InChiKey: XDBKLFODBADBED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2901299090

反应信息

• 作为反应物：
  描述：

  2-甲基-7-十八碳烯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以6%的产率得到(+/-)-7,8-epoxy-2-methyloktadecane
  参考文献：
  名称：

  有机合成中的硅。某些昆虫性信息素的立体选择性合成

  摘要：

  三烷基甲硅烷基烯丙基阴离子被烷基卤化物烷基化，从而在区域和区域选择性地在双键处具有反式立体化学的γ-产物。将反式-乙烯基硅烷立体选择性地转化为Z-乙烯基碘。乙烯基碘化物与有机金属试剂的偶联产生Z-烯烃。该方法已应用于几种昆虫性信息素的合成。

  DOI：

  10.1016/0022-328x(85)87361-7
• 作为产物：
  描述：

  pentadecen-4-en-1-yl 4-methylbenzenesulfonate 、 ISOBUTYLMAGNESIUM BROMIDE 、 氯化铵 在 dilithium tetrachlorocuprate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-甲基-7-十八碳烯
  参考文献：
  名称：

  SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES

  摘要：

  本发明涉及一种利用烯烃交换催化剂从廉价、易获得的起始材料合成昆虫信息素，特别是鳞翅目昆虫信息素及其前体和衍生物的方法。

  公开号：

  US20130231499A1

文献信息

• Process for the preparation of 7,8-epoxy-2-methyloctadecane
  申请人：Chemische Werke Huls Aktiengesellschaft

  公开号：US04036858A1

  公开（公告）日：1977-07-19

  7,8-Epoxy-2-methyloctadecane is economically prepared by a metathesis reaction of 7-methyl-1-octene and 1-dodecene to form 2-methyl-7-octadecene which is then epoxidized to give the desired product.

  7,8-环氧基-2-甲基十八烷通过7-甲基-1-辛烯和1-十二烯的交换反应制备，形成2-甲基-7-十八烯，然后进行环氧化反应得到所需的产物。这种方法经济实用。
• Synthesis of alkenes from carbonyl compounds and carbanions alpha to silicon. III. Full report and a synthesis of the sex pheromone of gypsy moth
  作者：T. H. Chan、E. Chang

  DOI：10.1021/jo00936a020

  日期：1974.11
• Response and Adaptation to Analogs of Disparlure by Specialist Antennal Receptor Neurons of Gypsy Moth, Lymantria dispar
  作者：Joseph C. Dickens、James E. Oliver、Victor C. Mastro

  DOI：10.1023/b:joec.0000006439.21448.53

  日期：1997.9

  Reception and adaptation of antennal receptors in response to (+)-disparlure [(+)-D], the sex attractant pheromone of the gypsy moth, Lyman tria dispar-(Lepidoptera: Lymantriidae)], its enantiomer, (-)-D, and analogs of disparlure in which the epoxide group is replaced with various three-membered rings [(+/-)-cyclopropyl (2HC), (+/-)-difluorocyclopropyl (2FC), (+/-)-dichlorocyclopropyl (2ClC), and (+/-)-aziridinyl (AZ), (+)-AZ, and (-)AZ] as well as a mixture of 1,1-epoxy analogs were investigated using electroantennograms. Antennal receptors of male moths were more responsive (5 mu g stimulus load) to (+)-D than to (-)-D; while responses to each of the analogs were significantly less and did not differ from each other. Antennal receptors of female moths did not respond significantly to any of the compounds at this stimulus load. Dose-response curves revealed greater sensitivity of male antennae to (+)-D than (-)-D. Among the cyclopropane analogs and 1,1-epoxy mixture (1,IE), the order of sensitivity was: 2FC > 2ClC > 2HC > 1,1E. Antennae were least sensitive to the aziridinyl analogs; however, (+)-AZ was more active than (-)-AZ, while an intermediate response was elicited by the racemate. Males exposed to (+)-D adapted to (+)-D, while responses to (+)-D were not significantly affected by exposure to (-)-D, 2FC or (+)-AZ. After exposure to hexylacetate, males showed adaptation to (+)D or (-)-D, but not to the other odorants. Preliminary field data correlate well with knowledge obtained in our electrophysiological studies and demonstrate the usefulness of such studies. These results indicate that novel approaches to the design and synthesis of potential agonists of disparlure receptors are necessary before substantial effects on the activity of disparlure are realized.
• Silicon in organic synthesis. Stereoselective synthesis of some insect sex pheromones
  作者：T.H. Chan、K. Koumaglo

  DOI：10.1016/0022-328x(85)87361-7

  日期：1985.4

  stereo-selectively the γ-product with trans-stereochemistry at the double bond. The trans-vinylsilanes are transformed stereoselectively to Z-vinyl iodides. Coupling of the vinyl iodides with organometallic reagents gives Z-alkenes. This approach has been applied to the synthesis of several insect sex pheromones.

  三烷基甲硅烷基烯丙基阴离子被烷基卤化物烷基化，从而在区域和区域选择性地在双键处具有反式立体化学的γ-产物。将反式-乙烯基硅烷立体选择性地转化为Z-乙烯基碘。乙烯基碘化物与有机金属试剂的偶联产生Z-烯烃。该方法已应用于几种昆虫性信息素的合成。
• SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES
  申请人：California Institute of Technology

  公开号：US20130231499A1

  公开（公告）日：2013-09-05

  The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

  本发明涉及一种利用烯烃交换催化剂从廉价、易获得的起始材料合成昆虫信息素，特别是鳞翅目昆虫信息素及其前体和衍生物的方法。