(1E,3E)-1-bromohepta-1,3-diene

• 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: (1E,3E)-1-bromohepta-1,3-diene
• 英文别名: (E,E)-1-bromohepta-1,3-diene
• 化学式: C₇H₁₁Br
• 分子量: 175.068
• InChiKey: RQLNMZLEJJTAEJ-YTXTXJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  聚合甲醛 、 (3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one 、 (1E,3E)-1-bromohepta-1,3-diene 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 2.34h， 以37%的产率得到(3aS,5R,6R,7aS)-6-[(1E,3E)-hepta-1,3-dienyl]-5-(hydroxymethyl)-2,2-dimethyl-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-4-one
  参考文献：
  名称：

  Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics

  摘要：

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.

  DOI：

  10.1021/jo991225z
• 作为产物：
  描述：

  2-已烯醛 、 三溴甲烷 在 四氯化钛 、 magnesium 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 (1Z,3E)-1-bromohepta-1,3-diene 、 (1E,3E)-1-bromohepta-1,3-diene
  参考文献：
  名称：

  A new entry of highly nucleophilic CHBr3–TiCl4–Mg system for the stereoselective synthesis of 1-alkenyl bromides

  摘要：

  This TiCl4-Mg promoted coupling of CHBr3 with various aldehydes and ketones, especially in sterically hindered or enolizable ketones, provides a simple, practical, and stereoselective carbonyl-bromomethylenation leading primarily to (E)-vinyl bromides. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.123

文献信息

• LIQUID CRYSTAL POLYMERS
  申请人：THE SECRETARY OF STATE FOR DEFENCE

  公开号：EP0858474A1

  公开（公告）日：1998-08-19
• US6030668A
  申请人：——

  公开号：US6030668A

  公开（公告）日：2000-02-29
• [EN] LIQUID CRYSTAL POLYMERS<br/>[FR] POLYMERES A CRISTAUX LIQUIDES
  申请人：THE SECRETARY OF STATE FOR DEFENCE

  公开号：WO1997016472A1

  公开（公告）日：1997-05-09

  (EN) Compounds of formula (I) are provided which may be used in a variety of devices including liquid crystal devices, piezoelectric devices, pyroelectric devices and in optical recording media; in said formula n = at least 5; Rx, Ry, Rz are independently selected from formula (IA), wherein Y is selected from COO, OCO, O, S, CHOH, CHF, CH2; Q = (CH2)n wherein one or more non-adjacent methylenes may be replaced by O and n = 1 - 20; Z is selected from O, S, single covalent bond, COO, OCO; when Y is CH2 then n may also be 0; (IB) represents any mesogenic group; Rx, Ry, Rz are also independently selected from H, OH, OCOR1, COOH, CO2R1, (CH2)pOH, (CH2)pCO2H, -(CH2)pOR1 or -(CH2)pCO2R1 and p = 1 - 20, R1 = H or C1-16 alkyl; when R1 = C2-16 alkyl the terminal CH3 group may be replaced by Br or Cl; provided that at least one of Rx, Ry, Rz is selected from formula (IA).(FR) L'invention concerne des composés représentés par la formule (I), qu'on peut utiliser dans une variété de dispositifs, y compris des dispositifs à cristaux liquides, des dispositifs piézo-électriques, des dispositifs pyroélectriques, ainsi que dans des supports d'enregistrement optique: dans cette formule, n = au moins 5; Rx, Ry, Rz sont sélectionnés indépendamment dans la formule (IA): dans laquelle Y est sélectionné parmi COO, OCO, O, S, CHOH, CHF, CH2; Q = (CH2)n où un ou plusieurs méthylènes non contigus peuvent être remplacés par O et n = 1-20; Z est sélectionné parmi O, S, une liaison covalente simple, COO, OCO; quand Y représente CH2, n peut également être 0; (IB) représente un groupe mésogène quelconque; Rx, Ry, Rz sont également sélectionnés indépendamment parmi H, OH, OCOR1, COOH, CO2R1, (CH2)pOH, (CH2)pCO2H, -(CH2)pOR1 ou -(CH2)pCO2R1 et p = 1-20, R1 = H ou alkyle C1-16; quand R1 = alkyle C2-16, le groupe terminal CH3 peut être remplacé par Br ou Cl; à condition qu'au moins l'un des symboles Rx, Ry, Rz soit sélectionné dans la formule (IA).
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
• A new entry of highly nucleophilic CHBr3–TiCl4–Mg system for the stereoselective synthesis of 1-alkenyl bromides
  作者：Yeshwant Ramchandra Bhorge、Su-Haur Chang、Cheng-Ta Chang、Tu-Hsin Yan

  DOI：10.1016/j.tet.2012.03.123

  日期：2012.6

  This TiCl4-Mg promoted coupling of CHBr3 with various aldehydes and ketones, especially in sterically hindered or enolizable ketones, provides a simple, practical, and stereoselective carbonyl-bromomethylenation leading primarily to (E)-vinyl bromides. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.