1-bromo-9-iodo-nonane | 926923-53-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-bromo-9-iodo-nonane
• 英文别名: 1-Bromo-9-iodononane
• CAS: 926923-53-7
• 化学式: C₉H₁₈BrI
• 分子量: 333.05
• InChiKey: YEMQZARGYZZILB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  11
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1,2-三溴-2-己基-环丙烷 、 1-bromo-9-iodo-nonane 在 六甲基磷酰三胺 、 正丁基锂 作用下， 生成 1-(9-Bromo-nonyl)-2-hexyl-cyclopropene
  参考文献：
  名称：

  Structure−Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori

  摘要：

  According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C-16 chain and the 11,12-position in a C-14 or C-18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E,12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 mu g/gland, but other compounds at 1 mu g/gland inhibited the conversion of [16,16, 16-H-2(3)]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C-16 chain was the strongest (I-50 = 0.016 mu g/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-C-14]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the all-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Delta 10,- 12-desaturation by 11,12- and 13,14-methylene compounds.

  DOI：

  10.1021/jf950757n
• 作为产物：
  描述：

  9-溴-1-壬醇 在 二乙胺基三氟化硫 、 magnesium iodide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 1-bromo-9-iodo-nonane
  参考文献：
  名称：

  通过使用具有杂原子取代基的镁试剂将烷基氟化物的 (sp3)C-F 键转化为 (sp3)C-杂原子（杂原子 = I、SR、SeR、TeR）键

  摘要：

  已经开发了一种将 (sp 3 )CF 键转换为 (sp 3 )CZ (Z = I, SR, SeR, TeR) 键的简便方法。该反应在室温下使用镁盐 (Z-MgX) 进行。用 MgI 2 在醚中取代伯烷基氟化物的 SN 2 机制得到了连接到 F 的碳的立体化学反转的支持。

  DOI：

  10.1246/cl.2007.196

文献信息

• 1-HALOALKADIENE AND A PROCESS FOR PREPARING THE SAME AND A PROCESS FOR PREPARING (9e, 11z)-9,11-HEXADECADIENYL ACETATE
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20190322614A1

  公开（公告）日：2019-10-24

  A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH 3 —(CH 2 ) 3 —CH═CH—CH═CH—(CH 2 ) a —X.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC—CH═CH—(CH 2 ) a —X, and a triarylphosphonium pentylide of the general formula (3): CH 3 —(CH 2 ) 3 —CH − —P + Ar 3 , to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.

  一种制备（9E,11Z）-9,11-十六烯基乙酸酯的方法，具有良好产率和高纯度，通式如下（1）：CH3—(CH2)3—CH═CH—CH═CH—( )a—X。该方法包括进行维特格反应的步骤，反应物为通式（2）：OHC—CH═CH—( )a—X的卤代烯醛，与通式（3）： —( )3—CH−—P+Ar3的三芳基膦五元阴离子，以获得1-卤代烯烃，并利用该方法获得的（7E,9Z）-1-卤代-7,9-十四烯烃，用于制备（9E,11Z）-9,11-十六烯基乙酸酯的方法。
• DIALKOXYALKENYL ALKOXYMETHYL ETHER COMPOUND AND A PROCESS FOR PREPARING A TERMINAL CONJUGATED ALKADIENAL COMPOUND FROM THE SAME
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20220106247A1

  公开（公告）日：2022-04-07

  The present invention provides a process for preparing a terminal conjugated alkadienal compound of the following general formula (5): CH 2 ═CHCH═CH(CH 2 ) a CHO   (5) wherein “a” represents an integer of 1 to 15, from a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R 1 CH 2 OCH 2 OCH 2 CH 2 CH═CH(CH 2 ) a CH(OR 2 )(OR 3 )   (1) wherein R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, R 2 and R 3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R 2 and R 3 may form together a divalent hydrocarbon group, R 2 -R 3 , having 2 to 10 carbon atoms, and “a” is as defined above.

  本发明提供了一种从以下通式（1）的二烷氧基烯丙基烷氧甲基醚化合物制备以下通式（5）的末端共轭烯二醛化合物的方法：R1 O O CH═CH(CH2)aCH(OR2)(OR3)   (1)，其中R1表示氢原子、具有1-9个碳原子的n-烷基或苯基，R2和R3独立地表示具有1-15个碳原子的单价碳氢基团，或者R2和R3可一起形成具有2-10个碳原子的双价碳氢基团R2-R3，而“a”如上所定义。
• 1-HALOALKADIENE AND PROCESS FOR PREPARING THE SAME AND A PROCESS FOR PREPARING (9E,11Z)-9,11-HEXADECADIENYL ACETATE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3556742A1

  公开（公告）日：2019-10-23

  The object of the invention is to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity. The present invention provides a process for preparing a 1-haloalkadiene of the general formula (1): CH3-(CH2)3-CH=CH-CH-CH-(CH2)a-X, comprising a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC-CH=CH-(CH2)a-X, and a triarylphosphonium pentylide of the general formula (3): CH3-(CH2)3-CH--P+Ar3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E,11Z)-9,11-hexadecadienyl acetate.

  本发明的目的是制备收率高、纯度高的(9E,11Z)-9,11-十六碳二烯乙酸酯。 本发明提供了一种制备通式（1）的 1-卤代碳二烯的工艺：CH3-(CH2)3-CH=CH-CH-CH-( )a-X，包括在通式(2)的卤代烯醛之间进行维蒂希反应的步骤：OHC-CH=CH-( )a-X的卤代烯醛与通式(3)的三芳基戊基鏻之间进行威蒂什反应： -( )3-CH--P+Ar3之间的反应，得到1-卤代烷二烯，并将通过该工艺得到的(7E,9Z)-1-卤代-7,9-十四烷二烯用于制备(9E,11Z)-9,11-十六烷二烯乙酸酯的工艺中。
• HALOALKENYL ALKOXYMETHYL ETHER COMPOUND AND A PROCESS FOR PREPARING A TERMINAL CONJUGATED ALKADIEN-1-YL ACETATE COMPOUND AND A TERMINAL CONJUGATED ALKADIEN-1-OL COMPOUND THEREFROM
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3978464A1

  公开（公告）日：2022-04-06

  The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R1CH2OCH2OCH2CH2CH=CH(CH2)aX1 (1) wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X1 represents a halogen atom, and "a" represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH2=CHCH=CH(CH2)aOAc (5) wherein "a" is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH2=CHCH=CH(CH2)aOH (6) wherein "a" is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

  本发明涉及下通式(1)的卤代烯基烷氧基甲基醚化合物：R1 O O CH=CH(CH2)aX1 (1) 其中 R1 代表氢原子、具有 1 至 9 个碳原子的正烷基或苯基，X1 代表卤素原子，"a "代表 3 至 14 的整数。本发明还涉及制备以下通式（5）的末端共轭烷二烯-1-基乙酸酯化合物的工艺： ＝CHCH＝CH( )aOAc(5)，其中 "a "如上定义，Ac 代表乙酰基，以及下通式(6)的末端共轭烷二烯-1-醇化合物： =CHCH=CH( )aOH(6)，其中 "a "如上定义，来自卤代烯基烷氧甲基醚化合物(1)。
• 1-haloalkadiene and a process for preparing the same and a process for preparing (9e, 11z)-9,11-hexadecadienyl acetate
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US10737999B2

  公开（公告）日：2020-08-11

  A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH3—(CH2)3—CH═CH—CH═CH—(CH2)a—X.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC—CH═CH—(CH2)a—X, and a triarylphosphonium pentylide of the general formula (3): CH3—(CH2)3—CH−—P+Ar3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.

  一种制备通式(1)的(9E,11Z)-9,11-十六碳二烯乙酸酯的工艺，产率高，纯度高：CH3-(CH2)3-CH═CH-CH═CH-( )a-X.=该工艺包括在通式(2)的卤代烯醛之间进行维蒂希反应的步骤：OHC-CH═CH-( )a-X与通式(3)的三芳基戊基鏻之间进行威蒂什反应： -( )3-CH--P+Ar3，得到1-卤代烷二烯，并将该工艺得到的(7E,9Z)-1-卤代-7,9-十四烷二烯用于制备(9E,11Z)-9,11-十六烷二烯乙酸酯的工艺。