9,11-Tetrdecadien-1-ol | 945529-61-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9,11-Tetrdecadien-1-ol
• 英文别名: 9,11-tetradecadien-1-ol；tetradeca-9,11-dien-1-ol
• CAS: 945529-61-3
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: ZKCFLTTYWFSLDK-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±11.0 °C(Predicted)
• 密度：
  0.860±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  9,11-Tetrdecadien-1-ol 在 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 生成 Acetic acid 8-(3'-ethyl-[2,2']bioxiranyl-3-yl)-octyl ester
  参考文献：
  名称：

  Investigation of aliphatic dienes by chemical ionization with nitric oxide

  摘要：

  AbstractIt is shown that the position of the double bond close to the hydrocarbon end of an aliphatic diene functionalized at C(1) can readily be determined by chemical ionization with NO+. Owing to the low abundance of the ions characteristic for the position of the other double bond, its localization may be difficult. Measurement of the chemical ionization (nitric oxide as reagent gas) spectra of the corresponding epoxides or collision activation studies can help.

  DOI：

  10.1002/oms.1210261205
• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 Lindlar's catalyst manganese(IV) oxide 、 lithium amide 、 potassium tert-butylate 、 氨 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 为溶剂， 生成 9,11-Tetrdecadien-1-ol
  参考文献：
  名称：

  Olefinic acetates, Δ-9,11–14: OAc and Δ-7,9–12: OAc used as sex pheromone components in three geometrid moths,Idaea aversata, I. straminata, andI. biselata (Geometridae, Lepidoptera)

  摘要：

  Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C-17 to C-21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11-tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9-dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11-tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding to (Z,Z)-7,9-dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11-tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

  DOI：

  10.1007/bf02027728

文献信息

• Pheromone XXXIV. Synthese konjugiert-ungesättigter Lepidopterenpheromone und Analoga
  作者：Hans Jürgen Bestmann、Joachim Süß、Otto Vostrowsky

  DOI：10.1002/jlac.198119811205

  日期：1981.12.24

  Nach Art eines “Baukastensystems” werden konjugiert-ungesättigte Alkadienylacetate, Alkadienole und Alkadienale, wie sie als Sexualpheromone weiblicher Schmetterlinge bekannt sind, mit unterschiedlichen Positionen und Geometrien der Doppelbindungen synthetisiert.

  以“模块系统”的方式，合成了共轭-不饱和乙酸链二烯基乙酸酯，链二烯醇和链二烯醛，它们被称为雌性蝴蝶的性信息素，其双键的位置和几何结构不同。
• AGRICULTURAL PHEROMONE COMPOSITIONS COMPRISING POSITIONAL ISOMERS
  申请人：PROVIVI, INC.

  公开号：US20170135343A1

  公开（公告）日：2017-05-18

  The present disclosure provides pheromone compositions. In some aspects, the compositions taught herein comprise a pheromone chemically corresponding to the pheromone naturally produced by a given insect, along with at least one positional isomer of said pheromone. In various aspects, pheromone compositions of the present disclosure are able to modulate the response of the insect based on the ratio of natural pheromone to its positional isomer.

  本公开提供信息素组合物。在某些方面，本文所教授的组合物包括一种与某种昆虫自然产生的信息素在化学上相对应的信息素，以及至少一种该信息素的位置异构体。在各个方面，本公开的信息素组合物能够通过自然信息素与其位置异构体的比例来调节昆虫的反应。
• Method for Producing Asymmetric Conjugated Diyne Compound and Method for Producing Z,Z-Conjugated Diene Compound Using the Same
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20160229829A1

  公开（公告）日：2016-08-11

  Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z 1 —Y 1 to a coupling reaction with an alkynyl halide (2) Y 2 —Z 2 —C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y 2 —Z 2 —C≡C—C≡C—Z 1 —Y 1 . In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

  提供了一种从廉价且安全的替代化合物制备不对称共轭二炔的方法，而不是羟胺盐酸盐，并且提供了一种从所得的不对称共轭二炔化合物制备Z,Z-共轭二烯化合物的方法。更具体地，提供了一种制备不对称共轭二炔化合物的方法，包括以下步骤：将末端炔基化合物（1）：HC≡C—Z1—Y1与炔基卤化物（2）Y2—Z2—C≡C—X在水和有机溶剂中使用硼氢化钠、铜催化剂和碱的情况下进行偶联反应，以获得不对称共轭二炔化合物（3）：Y2—Z2—C≡C—C≡C—Z1—Y1。此外，还提供了通过还原所得的不对称共轭二炔化合物等来制备Z,Z-共轭二烯化合物的方法。
• Syntheses with sulfones XLVII : stereoselective access to 1,3- and 1,4-dienes through hydrogenolysis of benzenesulfonyldienes. Application to pheromone synthesis
  作者：T. Cuvigny、C.Herve Du Penhoat、M. Julia

  DOI：10.1016/s0040-4020(01)90023-7

  日期：1987.1

  The stereospecific reduction of EE 2-benzenesulfonyl-1,3-dienes to ZE 1,3-dienes with Grignard reagents under transition metal catalysis ie described, Hydrogenolysis of the sulfonyl moiety of 2-benzenesulfonyl-1,4-dienes to ZE 1,4-dienes with sodium dithionite ie reported. These techniques have been applied to the stereoselective synthesis of (7E, 9Z) dodecadienyl acetate 3d, (9Z, 11E)tetradecadienyl

  在过渡金属催化下，用格氏试剂将EE 2-苯磺酰基-1,3-二烯立体定向还原为ZE 1,3-二烯，即描述为2-苯磺酰基-1,4-二烯的磺酰基部分加氢水解为ZE 1，据报道有4-二烯与连二亚硫酸钠。这些技术已经应用于（7E，9Z）乙酸十二碳二烯基3d，（9Z，11E）乙酸十四碳二烯基3e和（9Z，12E）乙酸四癸二烯基6b的立体选择性合成。
• 一种斜纹夜蛾性信息素制备方法
  申请人：南京一诺生物科技有限公司

  公开号：CN109608308A

  公开（公告）日：2019-04-12

  本发明公开了一种斜纹夜蛾性信息素制备方法，包括以下步骤：S1，合成9‑溴‑1壬醇；S2，在氮气保护下，合成三笨基磷溴化季铵盐；S3，合成9,11‑十四碳二烯‑1‑醇；S4，合成(Z,E)‑9,11十四碳二烯‑1‑醇；S5，合成(Z,E)‑9,11十四碳二烯‑1‑醇乙酸酯。本发明通过廉价易得的1，9‑壬二醇为原料，与48％HBr水溶液反应，以90％收率制得9‑溴‑1壬醇，单嗅化物9‑溴‑1壬醇收率较高，最后(Z,E)‑9,11十四碳二烯‑1‑醇与乙酸酐、吡啶反应合成(Z,E)‑9,11十四碳二烯‑1‑醇乙酸酯，纯度高达99.2％；本发明通过减压蒸除溶剂，剩余物经快速硅胶柱层析法，该纯化方法成本低，适合大规模推广。