(-)-monachalure | 182822-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (-)-monachalure
• 英文别名: 7S,8R-epoxy-octadecane；(7s,8r)-cis-7,8-Epoxy-octadecane；(2R,3S)-2-decyl-3-hexyloxirane
• CAS: 182822-08-8
• 化学式: C₁₈H₃₆O
• 分子量: 268.483
• InChiKey: ABMJUFOPOPEJRG-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 二甲基亚砜 、 原乙酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 29.75h， 生成 (-)-monachalure
  参考文献：
  名称：

  由2,3-丁二缩醛合成异戊二烯和莫纳丘利尔对映体

  摘要：

  2,3-丁二缩醛衍生物用于不对称取代的顺式环氧化物的立体选择性合成。该方法适用于使用甲基（2 S，3 R，5 R，6 ）制备Disparlure和Monachalure的对映异构体，吉普赛蛾（Lymantria dispar）和尼姑蛾（Lymantria monacha）的性信息素的成分。R）-3-乙基硫烷基羰基-5,6-二甲氧基-5,6-二甲基-1,4-二恶烷-2-羧酸酯为起始原料。

  DOI：

  10.3762/bjoc.16.57

文献信息

• [EN] SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION<br/>[FR] SYNTHÈSE D'ALCOOLS OLÉFINIQUES PAR L'INTERMÉDIAIRE DE L'HYDROXYLATION TERMINALE ENZYMATIQUE
  申请人：PROVIVI INC

  公开号：WO2015176020A1

  公开（公告）日：2015-11-19

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了一种通过将不饱和或饱和碳氢基质与羟化酶酶接触来生产末端羟基化烯烃和炔烃的方法。用于执行本发明方法的示例末端羟化酶对碳氢基质的一个末端碳具有很强的选择性，包括但不限于非血红素双铁脂烷单氧酶、细胞色素P450（例如，CYP52和CYP153家族的细胞色素P450）以及长链烷烃羟化酶。在某些实施例中，末端羟基化的烯烃或炔烃进一步转化为末端烯醛。在某些实施例中，末端羟基化的烯烃和炔烃可用作改变昆虫行为的昆虫信息素。在其他实施例中，末端羟基化的烯烃和炔烃是通过乙酰化或氧化醇基团来生产信息素的有用中间体。
• 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。
• SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
  申请人：Provivi, Inc.

  公开号：US20160108436A1

  公开（公告）日：2016-04-21

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了一种通过将不饱和或饱和的碳氢基质与一种羟化酶酶接触来生产端羟基化烯烃和炔烃的方法。用于执行本发明方法的示例端羟化酶对碳氢基质中的一个端碳具有强选择性，包括但不限于非血红素二铁烷烃单加氧酶、细胞色素P450（例如CYP52和CYP153家族的细胞色素P450）以及长链烷烃羟化酶。在某些实施例中，端羟基化的烯烃或炔烃进一步转化为端烯醛。在某些实施例中，端羟基化的烯烃和炔烃可用作改变昆虫行为的昆虫信息素。在其他实施例中，端羟基化的烯烃和炔烃是通过醋酸化或氧化醇基团来产生信息素的有用中间体。
• Synthesis of olefinic alcohols via enzymatic terminal hydroxylation
  申请人：PROVIVI, INC.

  公开号：US10202620B2

  公开（公告）日：2019-02-12

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了通过使不饱和或饱和烃底物与羟化酶接触来生产末端羟化的烯烃和炔烃的方法。用于实施本发明方法的典型末端羟化酶对烃底物的一个末端碳具有强选择性，包括但不限于非血红素二铁烷烃单氧化酶、细胞色素 P450（例如 CYP52 和 CYP153 家族的细胞色素 P450）以及长链烷烃羟化酶。在某些实施方案中，末端羟化的烯或炔进一步转化为末端烯醛。在某些实施方案中，末端羟基化的烯烃和炔烃可用作昆虫信息素，改变昆虫的行为。在其他实施方案中，末端羟基化的烯烃和炔烃是通过乙酰化或氧化醇分子生产信息素的有用中间体。
• US5683708A
  申请人：——

  公开号：US5683708A

  公开（公告）日：1997-11-04