(5E,7Z)-5,7-dodecadiene-1-ol | 72922-18-0

• 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: (5E,7Z)-5,7-dodecadiene-1-ol
• 英文别名: (5E,7Z)-dodeca-5,7-dien-1-ol；(5E,7E)-5,7-dodecadien-1-ol；(5E,7Z)-5,7-Dodecadien-1-ol；(E,Z)-5,7-Dodecadien-1-ol；(5E,7Z)-dodecadien-1-ol；dodeca-5E,7Z-dien-1-ol；5E,7Z-Dodecadien-1-ol
• CAS: 72922-18-0
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: JUDKGQZMLJXRJX-IGTJQSIKSA-N

物化性质

• 保留指数：
  1514;1514;1514;1514

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5E,7Z)-5,7-dodecadiene-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(5E,7Z)-5,7-dodecadienal
  参考文献：
  名称：

  信息素，XL。立体选择性合成的天芥菜种（鳞翅目）的信息素复合物；松蛾Dendrolimus pini的性引诱剂

  摘要：

  5，7-十二碳烯醇，乙酸-十二碳烯基乙酸酯和-十二碳烯醛，它们被称为海藻科的性引诱剂，是通过维蒂希（Wittig）烯化反应制备的。发现（5 Z，7 E）-5,7-十二指肠松是松蛾Dendrolimus pini的信息素。

  DOI：

  10.1002/jlac.198219820712
• 作为产物：
  描述：

  7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 硫酸 、 氢气 、 sodium hexamethyldisilazane 、 nickel diacetate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙二胺 为溶剂， 反应 18.0h， 生成 (5E,7Z)-5,7-dodecadiene-1-ol
  参考文献：
  名称：

  Kovalev, B. G.; Rastegaeva, V. M.; Kurts, A. L., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1632 - 1638

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of some isomers of dodecadien-1-ol: Compounds related to the pine moth sex pheromone.
  作者：Tetsu AND、Manh HUYNH VU、Shigeo YOSHIDA、Nobutaka TAKAHASHI

  DOI：10.1271/bbb1961.46.717

  日期：——

  Four isomers of 5, 7-dodecadien-1-ol were previously proposed as being the sex pheromone of the pine moth. The isomers were stereoselectively synthesized from 1-hexyne and tetrahydropyranyl ether of 5-hexyn-1-ol. The (5Z, 7Z)-isomer was synthesized by a Chodkiewic Cadiot reaction followed by hydroboration, and other three isomers by novel synthetic methods including the addition of zirconocene hydride [Schwarz's reagent (C5H5)2Zn(H)Cl] to control the regioselective coupling reaction. The 5, 8- and 5, 9-dodecadien-1-ols were also synthesized by similar methods for comparison of their characteristics with the endogenous sex pheromone.

  过去曾提出5,7-十二碳二烯-1-醇的4种异构体为松树蚕的性信息素。这些异构体是通过对1-己炔和5-己炔-1-醇的四氢吡喃醚进行立体选择性合成得到的。(5Z, 7Z)异构体是通过Chodkiewic Cadiot反应和随后的硼氢化反应合成的，而其他三种异构体则是通过包括使用二茂锆氢化物[Schwarz试剂(C5H5)2Zn(H)Cl]调控区域选择性偶联反应的新颖合成方法获得的。5,8-和5,9-十二碳二烯-1-醇也通过类似方法合成，以便与内源性性信息素的特性进行比较。
• PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS
  申请人：PROVIVI, INC.

  公开号：US20170137365A1

  公开（公告）日：2017-05-18

  In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R 1 is independently selected from H, C 1-18 alkyl, and C 2-18 alkenyl; R 2b is C 1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

  在一个方面，该发明提供了一种合成脂肪烯衍生物的方法。该方法包括：a）在存在一种烯烃催化剂的条件下，将符合式I的烯烃与符合式IIb的交换反应伙伴接触，以形成符合式IIIb的交换产物；并b）将交换产物转化为脂肪烯衍生物。每个R1独立地选择自H、C1-18烷基和C2-18烯基；R2为C1-8烷基；下标y为0至17之间的整数；下标z为0至17之间的整数。在某些实施方式中，交换催化剂为钨催化剂或钼催化剂。在各种实施方式中，脂肪烯衍生物为信息素。还描述了信息素组合物及其使用方法。
• 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。
• PROCESS FOR PREPARING A FORMYLALKENYL ALKOXYMETHYL ETHER COMPOUND AND PROCESSES FOR PREPARING CONJUGATED DIENE COMPOUNDS FROM THE SAME
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20210300854A1

  公开（公告）日：2021-09-30

  The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R 3 CH 2 OCH 2 O(CH 2 ) a CH═CHCHO (2), wherein R 3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R 3 CH 2 OCH 2 O(CH 2 ) a CH═CHCH(OR 1 )(OR 2 ) (1), wherein R 1 and R 2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 1 and R 2 may form together a divalent hydrocarbon group, R 1 -R 2 , having 2 to 10 carbon atoms; and R 3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).

  本发明提供一种制备下述一般式（2）的甲醛烯基烷氧甲基醚化合物的方法：R3 O O(CH2)aCH═CHCHO（2），其中R3代表氢原子，具有1至9个碳原子的n-烷基或苯基；“a”代表1至10的整数。该过程包括：在酸的存在下水解下述一般式（1）的二烷氧基烯基烷氧甲基醚化合物：R3 O O( )aCH═CHCH(OR1)(OR2)（1），其中R1和R2分别独立地代表具有1至15个碳原子的单价碳氢基团，或R1和R2可形成具有2至10个碳原子的二价碳氢基团R1-R2；而R3和“a”如上所定义，同时去除生成的醇化合物以形成甲醛烯基烷氧甲基醚化合物（2）。
• MULTI-SUBSTRATE METABOLISM FOR IMPROVING BIOMASS AND LIPID PRODUCTION
  申请人：Provivi, Inc.

  公开号：EP3564377A1

  公开（公告）日：2019-11-06

  The present application relates to methods to improve biomass or lipid production in a microorganism from one or more fatty acid and one or more simple carbon co-substrates. Produced lipids may include unsaturated C6-C24 fatty acids, alcohols, aldehydes, and acetates which may be useful as final products or precursors to insect pheromones, fragrances, flavors, and polymer intermediates. The application further relates to recombinant microorganisms modified for improved production of biomass or lipid, or improved lipid selectivity. Also provided are methods of producing one or more lipid using the recombinant microorganisms, as well as compositions comprising the recombinant microorganisms and/or optionally one or more of the product lipid.

  本申请涉及提高微生物中一种或多种脂肪酸和一种或多种单碳共底物的生物量或脂质产量的方法。生产的脂质可包括不饱和 C6-C24 脂肪酸、醇、醛和乙酸酯，它们可用作昆虫信息素、香料、香精和聚合物中间体的最终产品或前体。本申请还涉及为改进生物质或脂质的生产或改进脂质选择性而改良的重组微生物。还提供了使用重组微生物生产一种或多种脂质的方法，以及包含重组微生物和/或一种或多种产品脂质的组合物。