3,13-十八碳二烯-1-醇 | 66410-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3,13-十八碳二烯-1-醇
• 中文别名: 顺-3,顺-13-十八碳二烯-1-醇
• 英文名称: (3Z,13Z)-3,13-octadecadienyl alcohol
• 英文别名: (3Z,13Z)-3,13-Octadecadien-1-ol；(Z,Z)-3,13-octadecadien-1-ol；3(Z),13(Z)-octadecadien-1-ol；(3Z,13Z)-octadecadien-1-ol；octadeca-3c,13c-dien-1-ol；3,13-Octadecadien-1-ol, (3Z,13Z)-；(3Z,13Z)-octadeca-3,13-dien-1-ol
• CAS: 66410-24-0
• 化学式: C₁₈H₃₄O
• 分子量: 266.467
• InChiKey: QBNCGBJHGBGHLS-NCCHCWSYSA-N

物化性质

• 保留指数：
  2065

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905290000

反应信息

• 作为反应物：
  描述：

  3,13-十八碳二烯-1-醇 在 吡啶 、 乙酸酐 作用下， 以100%的产率得到(3Z,13Z)-3,13-十八碳二烯-1-基乙酸酯
  参考文献：
  名称：

  6-HYDROXY-3-HEXENYL ALKOXYMETHYL ETHER COMPOUND AND A PROCESS FOR PREPARING A 3,13-OCTADECADIEN-1-OL COMPOUND FROM THE SAME

  摘要：

  本发明涉及以下通式（1）的6-羟基-3-己烯基烷氧甲基醚化合物：HOCH2CH2CH═CHCH2CH2OCH2OCH2R′（1），其中R1代表氢原子、具有1至9个碳原子的n-烷基或苯基；以及从6-羟基-3-己烯基烷氧甲基醚化合物（1）制备以下通式（6）的3,13-八十二碳二烯-1-醇化合物的方法：CH3(CH2)3CH═CH(CH2)8CH═CHCH2CH2OH（6）。

  公开号：

  US20220106252A1
• 作为产物：
  描述：

  1-iodo-10-undecene 在 potassium,trimethylsilanide 、 烯丙基溴化镁 作用下， 反应 26.0h， 生成 3,13-十八碳二烯-1-醇
  参考文献：
  名称：

  1,(ω - 1)-Dienes: solvent controlled unilateral or bilateral metalation

  摘要：

  In hexane, i.e. under heterogeneous conditions, 1,(omega-1)-dienes readily undergo double deprotonation to give bis(allylmetal) intermediates. In tetrahydrofuran at - 75 or - 50-degrees-C, however, only monometalation occurs with dienes having chains of up to 12 carbon atoms. The practical potential of such selective monosubstitution reactions is demonstrated by two novel pheromone syntheses.

  DOI：

  10.1016/0022-328x(91)86133-b

文献信息

• [EN] TETRAZOLINONE COMPOUNDS AND ITS USE AS PEST CONTROL AGENTS<br/>[FR] COMPOSÉS TÉTRAZOLINONE ET LEUR UTILISATION EN TANT QU'AGENTS DE LUTTE CONTRE LES NUISIBLES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2018097318A1

  公开（公告）日：2018-05-31

  The present invention provides a tetrazolinone represented by formula (I) and a pest control agent comprising the same, and their use thereof. Formula (I) [wherein, W1 represents an oxygen atom or a sulfur atom; W2 represents a hydrogen atom, or a C1-C6 chain hydrocarbon group; R15 and R16 represent a halogen atom and the like; u is 0, 1, 2 or 3; the combination of E, G, X1, Y1 and Z1 represents any one of the combinations of the following a and the like: a: a combination wherein E represents #-C(X1)(Y1)-O-N=C(Z1)-, #-C(X1)(Y1)-S-N=C(Z1)-, #-C(X1)(Y1)-O-N=C(Z1)-O-CH2-, #-C(X1)(Y1)-O-N=C(Z1)-S-CH2-, #-C(X1)(Y1)-S-N=C(Z1)-O-CH2-, #-C(X1)(Y1)-S-N=C(Z1)-S-CH2-, #-C(Z1)=N-N=C(Z2)-, #-C(X1)=C(Y1)-C(Z1)=N-O-CH2- or #-C(X1)=C(Y1)-C(Z1)=N-S-CH2-; G represents a C1-C6 chain hydrocarbon group, a (C1-C6 alkoxy)C1-C6 alkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group the C1-C6 chain hydrocarbon group, the (C1-C6 alkoxy)C1-C6 alkyl group, and the (C1-C6 alkylthio)C1-C6 alkyl group may have one or more substituents selected from Group S} or R1-T1-, X1 and Y1, which are identical to or different from each other, independently represents substituents selected from Group T, and Z1 represents a substituent selected from Group V.]

  本发明提供了一种由式(I)表示的四唑酮化合物，以及包含该化合物的杀虫剂，以及它们的使用。式(I)中，W1代表氧原子或硫原子；W2代表氢原子或C1-C6链烃基；R15和R16代表卤素原子等；u为0、1、2或3；E、G、X1、Y1和Z1的组合代表以下a等组合中的任意一种：a：E代表#-C(X1)(Y1)-O-N=C(Z1)-、#-C(X1)(Y1)-S-N=C(Z1)-、#-C(X1)(Y1)-O-N=C(Z1)-O-CH2-、#-C(X1)(Y1)-O-N=C(Z1)-S-CH2-、#-C(X1)(Y1)-S-N=C(Z1)-O-CH2-、#-C(X1)(Y1)-S-N=C(Z1)-S-CH2-、#-C(Z1)=N-N=C(Z2)-、#-C(X1)=C(Y1)-C(Z1)=N-O-CH2-或#-C(X1)=C(Y1)-C(Z1)=N-S-CH2-；G代表C1-C6链烃基、(C1-C6烷氧基)C1-C6烷基、(C1-C6烷硫基)C1-C6烷基C1-C6链烃基、(C1-C6烷氧基)C1-C6烷基和(C1-C6烷硫基)C1-C6烷基中的每一种可能具有来自S族的一个或多个取代基}或R1-T1-，X1和Y1互相相同或不同，独立地代表来自T族的取代基，Z1代表来自V族的取代基。
• Synthesis and Characterization of 3,13- and 2,13-Octadecadienyl Compounds for Identification of the Sex Pheromone Secreted by a Clearwing Moth,<i>Nokona pernix</i>
  作者：Hideshi NAKA、Tomotake NAKAZAWA、Mieko SUGIE、Masanobu YAMAMOTO、Yoshiteru HORIE、Ryohei WAKASUGI、Yutaka ARITA、Hajime SUGIE、Koji TSUCHIDA、Tetsu ANDO

  DOI：10.1271/bbb.70.508

  日期：2006.1

  Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M−18]+ at m⁄z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.

  通过乙炔偶联反应从1,8-辛二醇或1,9-壬二醇出发合成了3,13-和2,13-十八碳二烯-1-醇及其乙酸酯的几种几何异构体。除了商业上可获得的化合物外，每种二烯基化合物的所有几何异构体都通过NMR和GC-MS进行了分析，以积累用于研究从隶属于鳞翅目天蛾科的透翅蛾中分泌的性信息素的化学数据。尽管3,13-和2,13-二烯的乙酸酯衍生物显示出几乎相同的质谱，但通过比较[M−18]+在m/z 248处的相对强度，醇可以被区分开来，这表明可以直接区分这两种位置异构体而不需要衍生化。此外，每种几何异构体从高极性GC柱中流出时具有不同的保留时间。基于这些数据，通过GC-EAD和GC-MS分析了一种天蛾科蛾类Nokona pernix的性信息素腺提取物，并鉴定了两种EAG活性成分，即3,13-十八碳二烯-1-醇的(3E,13Z)-和(3Z,13Z)-异构体，比例为9:1。在田间，以9:1比例混合的合成化合物很好地吸引了N. pernix雄性，而单一成分很少吸引雄性。吸引的雄性数量在六月中旬达到高峰，八月份出现了一个小的高峰。
• 복숭아유리나방의 주요 성페로몬인 옥타데카디에닐 아세테이트의 제조방법
  申请人：LEE, Dong Ha 이동하(420130458499)

  公开号：KR20180056877A

  公开（公告）日：2018-05-30

  본 발명은 복숭아유리나방(cherry tree borer, Synanthedon bicingulate)을 방제하기 위하여 복숭아유리나방의 성페로몬을 제조하는 방법에 관한 것으로, 본 발명은 복숭아유리나방의 성페로몬의 주성분인 (3E,13Z)-옥타데카디에닐 아세테이트와 (3Z,13Z)-옥타데카디에닐 아세테이트 각각을 저렴한 출발물질로부터 효율적이고 간단하게 경제적이면서 우수한 순도와 입체 선택성으로 제조할 수 있는 방법을 제공한다.

  本发明涉及一种用于防治樱桃树蛀果蛾（Synanthedon bicingulate）的方法，该方法涉及制备樱桃树蛀果蛾的性信息素。本发明提供了一种从廉价起始原料高效、简单、经济且具有优异纯度和立体选择性地制备樱桃树蛀果蛾性信息素的方法，该性信息素的主要成分是(3E,13Z)-八十二烯醛醋酸酯和(3Z,13Z)-八十二烯醛醋酸酯。
• Pheromone 69.¹Stereoselektive Synthesen nichtkonjugierter bisolefinischer Lepidopteren-Pheromone und Strukturanaloger
  作者：Hans Jürgen Bestmann、Thomas Zeibig、Otto Vostrowsky

  DOI：10.1055/s-1990-27089

  日期：——

  Pheromones 69.1 Stereoselective Syntheses of Nonconjugated Bisolefinic Lepidoptera Pheromones and Structural Analogs Coupling reactions of lithium compounds, (Z)-carbonyl olefination of phosphonium ylides and "crossed" Wittig olefination of bisylides are the key reaction steps in the synthesis principle for nonconjugated, bisolefinic Lepidoptera pheromones and structural analogs. Double unsaturated (E,Z)- and (E,E)-1-vinyl halides are converted into the corresponding (E,Z)- and (E,E)-1-vinyl lithium compounds and coupled selectively to (E,Z)- and (E,E)-alkadienols, alkadienals and alkadienyl acetates with different carbon chain length, geometry and relative positions of double bonds. "Crossed" Wittig reactions of 1,ω-alkylidene bisylides with two different alkanals gives rise to the formation of corresponding (Z,Z)-dienic sex attractants and derivatives. A monounsaturated (E)-1-vinyl iodide is the synthon for the preparation of an (E)-alkenyl bromide which is converted to an (E)-alkenyl phosphonium salt and (Z)-selectively olefinated to (Z,E)-isomers of moth sex pheromones.

  信息素 69.1 非共轭双烯类鳞翅目昆虫信息素及其结构类似物的立体选择性合成 锂化合物的偶联反应、磷烷阳离子盐的(Z)-羰基烯化以及双阳离子的“交叉”维蒂格烯化是合成非共轭双烯类鳞翅目昆虫信息素及其结构类似物的关键反应步骤。双不饱和的(E,Z)-和(E,E)-1-烯基卤化物转化为相应的(E,Z)-和(E,E)-1-烯基锂化合物，然后选择性偶联生成不同碳链长度、几何结构及双键相对位置的(E,Z)-和(E,E)-烷二醇、烷二醛及烷二烯基醋酸酯。1,ω-烷基烯基双阳离子与两种不同烷基醛的“交叉”维蒂格反应生成相应的(Z,Z)-二烯性别吸引剂及其衍生物。单不饱和的(E)-1-烯基碘化物是制备(E)-烯基溴化物的合成子，后者转化为(E)-烯基磷烷盐，并选择性地烯化为蛾类性别信息素的(Z,E)-异构体。
• HETEROCYCLIC COMPOUND, AND HARMFUL-ARTHROPOD-CONTROLLING AGENT CONTAINING SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP3514155A1

  公开（公告）日：2019-07-24

  The present invention relates to a compound represented by Formula (I): in the formula, Q represents a group represented by Formula Q1, Q2, or Q3, and T represents a chain hydrocarbon group, an alkoxyalkyl group, an alkylsulfanylalkyl group, an alkylsulfinylalkyl group, or an alkylsulfonylalkyl group, which has a halogen atom; a cycloalkylalkyl group or a cycloalkyl group, which has a substituent; OR1, S(O)mR1, OS(O)2R1, CH2OR1, NR1R29, C(O)R1, C(O)NR1R29, NR21C(O)R1, N=CR1R30, or a group represented by any one of Formulae T-1 to T-12,

  本发明涉及一种由式（I）表示的化合物： 式中，Q 代表式 Q1、Q2 或 Q3 所代表的基团，T 代表链烃基、烷氧基烷基、烷硫基烷基、烷亚磺酰基烷基或烷磺酰基烷基，其中有一个卤原子；具有取代基的环烷基烷基或环烷基； OR1、S(O)mR1、OS(O)2R1、CH2OR1、NR1R29、C(O)R1、C(O)NR1R29、NR21C(O)R1、N=CR1R30 或由式 T-1 至 T-12 中任何一个所代表的基团、