(E)-1-iodo-1-tetradecene | 66827-09-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-1-iodo-1-tetradecene
• 英文别名: 1-iodotetradec-1-ene；(E)-1-iodotetradec-1-ene
• CAS: 66827-09-6
• 化学式: C₁₄H₂₇I
• 分子量: 322.273
• InChiKey: QILKOUAIVQIDOU-BUHFOSPRSA-N

物化性质

• 沸点：
  287.94°C (rough estimate)
• 密度：
  1.2078 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (E)-1-iodo-1-tetradecene 在 bis-triphenylphosphine-palladium(II) chloride 四氢吡咯 、 copper(l) iodide 、 红铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 17.0h， 生成 (2R,3Z,5E)-4-iodo-3,5-octadien-2-ol
  参考文献：
  名称：

  Efficient Synthesis of Akolactone AviaPd-Catalyzed Carbonylation

  摘要：

  本研究首次利用钯催化羰基化技术合成了(+)-和(-)-阿可内酯 A。通过比较阿可内酯 A 的两种对映体和天然化合物的旋光性，表明阿可内酯 A 的 4 位绝对构型为 R。

  DOI：

  10.1271/bbb.67.2658
• 作为产物：
  描述：

  溴代十二烷 在 二异丁基氢化铝 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (E)-1-iodo-1-tetradecene
  参考文献：
  名称：

  Efficient Synthesis of Akolactone AviaPd-Catalyzed Carbonylation

  摘要：

  本研究首次利用钯催化羰基化技术合成了(+)-和(-)-阿可内酯 A。通过比较阿可内酯 A 的两种对映体和天然化合物的旋光性，表明阿可内酯 A 的 4 位绝对构型为 R。

  DOI：

  10.1271/bbb.67.2658

文献信息

• Polymethylhydrosiloxane (PMHS) as an Additive in Sonogashira Reactions
  作者：Robert E. Maleczka Jr.、William P. Gallagher

  DOI：10.1055/s-2003-37522

  日期：——

  Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the Sonogashira reaction of a variety of alkynes and electrophiles. These couplings appear to involve the in situ formation and reaction of an alkynylsiloxane. Such couplings can be run amine free at room temperature, reaction times are short, workup is easy, and product purification is straightforward. Thus, the advantages (and disadvantages) of running Sonogashira couplings with 1-silylalkynes are realized, without the need to preform the alkynyl silane.

  聚甲基氢硅氧烷（PMHS）与氟化铯（CsF）结合，促进了多种炔烃与电亲核试剂的索诺加希拉反应。这些偶联反应似乎涉及到原位形成和反应炔基硅氧烷。这些偶联反应可以在室温下无胺进行，反应时间短，后处理简单，产品纯化直观。因此，利用1-硅基炔烃进行索诺加希拉偶联反应的优点（和缺点）得以实现，而无需预先制备炔基硅烷。
• PMHS-Mediated Couplings of Alkynes or Benzothiazoles with Various Electrophiles:  Application to the Synthesis of (−)-Akolactone A
  作者：William P. Gallagher、Robert E. Maleczka

  DOI：10.1021/jo034463+

  日期：2003.8.1

  Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the cross-coupling of alkynes or benzothiazoles with an array of vinyl, styryl, and aryl halides or nonaflates as well as acid chlorides. Experimental and spectroscopic evidence indicates that these reactions involve the in situ generation of a siloxyl intermediate. These cross-couplings proceed relatively quickly at room temperature

  聚甲基氢硅氧烷（PMHS）与CsF的结合有助于炔烃或苯并噻唑与一系列乙烯基，苯乙烯基和芳基卤化物或壬二酸酯以及酰基氯的交叉偶联。实验和光谱证据表明，这些反应涉及甲硅烷氧基中间体的原位生成。这些交叉偶联在室温和无胺条件下进行得相对较快。为了证明该方法的适用性，进行了全细胞毒性丁醇内酯（-）-可可内酯A的合成。
• Method for producing coupling compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20040161404A1

  公开（公告）日：2004-08-19

  There are disclosed a method for producing a cross-coupling compound of formula (3): (Y—) (n−1) R 1 —R 2 —(R 1 ) (n′−1) (3) wherein R 1 represents a substituted or unsubstituted, linear, branched, or cyclic hydrocarbon group, and n and n′ each represent 1 or 2, provided that when n and n′ are the same, both n and n′ are not 2, R 2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group, and Y represents R 2 or X 1 , wherein R 2 is as defined above, and X 1 represents a chlorine, bromine or iodine atom, which method comprises reacting an organic halide of formula (1): n′(R 1 X l n ), wherein R 1 is as defined above and carbon atoms at the &agr; and &bgr; positions relative to X 1 are sp 3 carbon atoms, and X 1 , n and n′ are as defined above, with a boron compound of formula (2): m{R 2 (BX 2 2 ) n′ }, wherein R 2 and n′ are as defined above, X 2 independently represents a hydroxyl group or an alkoxy or aryloxy group, or X 2 2 together form an alkoxy or aryloxy group, and m represents 1 or 2, and m≧n, and the boron atom is bonded with a sp 2 carbon atom of R 2 group, or a boronic acid trimer anhydride thereof, in the presence of a base and a catalyst comprising a nickel compound and a compound of formula (i): 1 wherein R 3 represents a substituted or unsubstituted alkyl group, R 4 represents a hydrogen atom or an substituted or unsubstituted alkyl group, l represents an integer of 1 to 3, and p and q each represents an integer of 0 to 2; and a catalyst.

  本发明公开了一种制备交叉偶联化合物的方法，该化合物的化学式为（3）：（Y-）（n-1）R1-R2-（R1）（n' -1）（3），其中R1代表取代或未取代的线性、支链或环烃基，n和n'各自代表1或2，但当n和n'相同时，n和n'均不为2；R2代表取代或未取代的芳基、取代或未取代的杂环基或取代或未取代的烯基，Y代表R2或X1，其中R2如上所定义，X1代表氯、溴或碘原子。该方法包括将化学式为（1）的有机卤化物与化学式为（2）的硼化合物在碱和催化剂的存在下反应，其中化学式（1）中R1如上所定义，X1、n和n'如上所定义，α和β位置相对于X1的碳原子为sp3碳原子，化学式（2）中R2和n'如上所定义，X2独立代表羟基或烷氧基或芳氧基，或X22共同形成烷氧基或芳氧基，m代表1或2，m≤n，硼原子与R2基的sp2碳原子或其硼酸三聚体酐键合。催化剂包括一种镍化合物和一种化学式为（i）的化合物：1其中R3代表取代或未取代的烷基，R4代表氢原子或取代或未取代的烷基，l代表1至3的整数，p和q分别代表0至2的整数。
• METHOD FOR PRODUCING COUPLING COMPOUND
  申请人：Itahashi Tamon

  公开号：US20060281925A1

  公开（公告）日：2006-12-14

  A method is provided for producing a specific crosscoupling compound and a specific catalyst for producing the compound. The method includes reacting in the presence of a base and a nickel compound catalyst organic halide of the formula n′(R 1 X 1 n ), wherein R 1 is a hydrocarbon group and the α and β carbons to X′ are sp 3 carbon atoms; X 1 is a chlorine, bromine, or iodine atoms, and n and n 1 are 1 or 2 but not both 2, with a compound having the formula mR 2 (BX 2 2 ) n′ } where an R 2 is an aryl, heteroaryl, or alkenyl group, and n′ is 1 or 2, X 2 is independently a hydroxyl group, an alkoxy or arylalkoxy group or X 2 2 together form an alkylenedioxy or arylenedioxy group, and m represents 1 or 2 but m≦n, and the boron atom is bonded to a sp 2 carbon atom of R 2 group or a boronic acid trimer anhydride.

  提供了一种生产特定交叉偶联化合物和特定催化剂以生产该化合物的方法。该方法包括在碱和镍化合物催化剂的存在下，将具有以下公式的有机卤化物n’（R1X1n）与具有以下公式的化合物m R2（BX22）n’}反应，其中R1是一个碳氢基团，α和β碳至X’是sp3碳原子；X1是氯、溴或碘原子，n和n1为1或2但不同时为2；R2是芳基、杂环芳基或烯基基团，n’为1或2，X2独立地是羟基、烷氧基或芳基烷氧基，或X22共同形成烷二酮基或芳二酮基；m表示1或2，但m≦n，硼原子与R2基团的sp2碳原子或硼酸三聚体酐键合。
• ORGANIC TRANSISTOR, COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL FOR NON-LUMINESCENT ORGANIC SEMICONDUCTOR DEVICE, MATERIAL FOR ORGANIC TRANSISTOR, COATING SOLUTION FOR NON-LUMINESCENT ORGANIC SEMICONDUCTOR DEVICE, AND ORGANIC SEMICONDUCTOR FILM FOR NON-LUMINESCENT ORGANIC SEMICONDUCTOR DEVICE
  申请人：Fujifilm Corporation

  公开号：EP3104426A1

  公开（公告）日：2016-12-14

  Provided are an organic transistor containing a compound, which is represented by the following formula, results in high carrier mobility when being used in a semiconductor active layer of the organic transistor, and exhibits high solubility in an organic solvent, in a semiconductor active layer; a compound; an organic semiconductor material for a non-light-emitting organic semiconductor device; a material for an organic transistor; a coating solution for a non-light-emitting organic semiconductor device; and an organic semiconductor film for a non-light-emitting organic semiconductor device (X is O, S, or Se; each of p and q is an integer of 0 to 2; each of R1 to R10, Ra, and Rb is hydrogen, halogen, or -L-R; one of R1 to R10, Ra, and Rb is -L-R; in a case where at least one of R5 or R6 is -L-R, L is an ethenyl group or an ethynyl group; L is a specific divalent linking group; and R is an alkyl group, a cyano group, a vinyl group, an ethynyl group, an oxyethylene group, an oligo-oxyethylene group in which a repetition number v of an oxyethylene unit is equal to or greater than 2, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group).

  本发明提供了一种有机晶体管，该有机晶体管含有一种化合物，该化合物由下式表示，当用于有机晶体管的半导体活性层时，可产生高载流子迁移率，并且在有机溶剂中具有高溶解性，在半导体活性层中；一种化合物；一种用于非发光有机半导体器件的有机半导体材料；一种用于有机晶体管的材料；一种用于非发光有机半导体器件的涂层溶液；以及一种用于非发光有机半导体器件的有机半导体薄膜（X 为 O、S 或 Se；p和q中的每一个都是0至2的整数；R1至R10、Ra和Rb中的每一个都是氢、卤素或-L-R；R1至R10、Ra和Rb中的一个是-L-R；在R5或R6中至少有一个是-L-R的情况下，L是乙烯基或乙炔基；L是特定的二价连接基团；以及 R 是烷基、氰基、乙烯基、乙炔基、氧乙烯基、氧乙烯单元的重复数 v 等于或大于 2 的低聚氧乙烯基、硅氧烷基、具有两个或两个以上硅原子的低聚硅氧烷基或三烷基硅烷基）。