(Z,E)-5,7-十二碳二烯醇 | 73416-72-5

• 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: (Z,E)-5,7-十二碳二烯醇
• 英文名称: (Z,E)-5,7-dodecadienol
• 英文别名: (5E,7E)-5,7-dodecadien-1-ol；(E)-5,(E)-7-Dodecadien-1-ol；(5E,7E)-dodecadien-1-ol；5E,7E-dodecadienol；dodeca-5t,7t-dien-1-ol；E-5,Z-7-dodecadienol；5,7-Dodecadien-1-ol；(5E,7E)-dodeca-5,7-dien-1-ol
• CAS: 73416-72-5
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: JUDKGQZMLJXRJX-BSWSSELBSA-N

物化性质

• 保留指数：
  1465

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：

  (Z,E)-5,7-十二碳二烯醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 (5E,7E)-5,7-dodecadienal
  参考文献：
  名称：

  Ando, Tetsu; Katagiri, Yoshio; Uchiyama, Masaaki, Agricultural and Biological Chemistry, 1985, vol. 49, # 2, p. 413 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(2-tetrahydropyranyloxy)pentanal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 42.0h， 生成 (Z,E)-5,7-十二碳二烯醇
  参考文献：
  名称：

  Ando, Tetsu; Kurotsu, Yuichi; Kaiva, Mieko, Agricultural and Biological Chemistry, 1985, vol. 49, # 1, p. 141 - 148

  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。
• Method for Producing Aldehyde and Ketone
  申请人：Yamashita Miyoshi

  公开号：US20110282102A1

  公开（公告）日：2011-11-17

  Provided is a highly efficient method for the production of aldehydes and ketones, which is inexpensive, exhibits high reactivity, and is capable of easy separation of byproduct after the reaction. More particularly, there is provided a method for producing an aldehyde or a ketone, comprising at least an oxidation step of oxidizing a primary alcohol or a secondary alcohol in the presence of a polymeric carbodiimide represented by the following formula (1) and having a weight-average molecular weight of 300 to 5000, and a sulfoxide compound, together with an acid and a base, or together with a salt of the acid and the base.

  提供了一种高效的生产醛和酮的方法，该方法廉价、具有高反应性，并能够在反应后轻松分离副产物。更具体地，提供了一种生产醛或酮的方法，包括至少一个氧化步骤，即在聚合物碳二亚胺（表示为以下式（1）且具有分子量为300至5000的重均分子量）和亚砜化合物的存在下氧化一级醇或二级醇，以及酸和碱，或者酸和碱的盐。
• 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。
• Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates
  申请人：Bedoukian Robert H.

  公开号：US20100113837A1

  公开（公告）日：2010-05-06

  Compounds of the formula (I) wherein R 2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH 2 OH, —CH 2 OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.

  式(I)的化合物中，其中R2为支链或未支链、饱和或含有乙烯单元或二元不饱和的脂肪基，Z为—CH2OH、—CH2OAc或—CHO，m为一个或多个正整数，Ac为乙酰基，通过以下过程合成：1-烯丙基烷基化合物与卤代烷醇格氏试剂反应。