1-溴-11-碘十一烷 | 139123-69-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 中文名称: 1-溴-11-碘十一烷
• 英文名称: 1-bromo-11-iodoundecane
• CAS: 139123-69-6
• 化学式: C₁₁H₂₂BrI
• 分子量: 361.104
• InChiKey: YIAXRTMSPXAUAF-UHFFFAOYSA-N

物化性质

• 沸点：
  333.1±10.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  13
• 可旋转键数：
  10
• 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-乙基环丙烷 、 1-溴-11-碘十一烷 在 六甲基磷酰三胺 、 正丁基锂 作用下， 生成 1-(11-Bromo-undecyl)-2-ethyl-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：

  11-溴-1-十一烯 在 bis-triphenylphosphine-palladium(II) chloride 三异丁基铝 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到1-溴-11-碘十一烷
  参考文献：
  名称：

  钯和其他后期过渡金属配合物催化的三异丁基铝催化烯烃的氢转移加氢铝化

  摘要：

  末端烯烃和二烯的氢转移加氢铝化反应可以达到1.1当​​量。（i- Bu）3 Al在室温下的催化产率高，且催化量的Cl 2 Pd（PPh 3）2和其他含Co，Rh，Ni和Pt的后期过渡金属配合物。

  DOI：

  10.1016/s0040-4039(00)02142-0

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—(CH2)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—(CH2)a—X的卤代烯醛，与通式（3）：CH3—(CH2)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。
• A mild, phosphine-free method for the conversion of alcohols into halides (Cl, Br, I) via the corresponding O-alkyl isoureas
  作者：Zhengning Li、Stefano Crosignani、Bruno Linclau

  DOI：10.1016/j.tetlet.2003.09.024

  日期：2003.10

  A novel procedure for the conversion of primary and secondary alcohols into the corresponding alkyl chlorides, bromides and iodides is described. The transformation is high-yielding in the case of chlorides and bromides, tolerates a range of functional groups, and does not rely on the use of phosphines.

  描述了将伯醇和仲醇转化为相应的烷基氯化物，溴化物和碘化物的新方法。在氯化物和溴化物的情况下，该转化是高产率的，可耐受一系列官能团，并且不依赖于膦的使用。
• 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：R1CH2OCH2OCH2CH2CH═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-(CH2)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-(CH2)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：CH3-(CH2)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：R1CH2OCH2OCH2CH2CH=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：CH2＝CHCH＝CH(CH2)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：CH2=CHCH=CH(CH2)aOH(6)，其中 "a "如上定义，来自卤代烯基烷氧甲基醚化合物(1)。