(2E,4Z)-2,4-dimethyl-2,4-nonadienol | 110897-38-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4Z)-2,4-dimethyl-2,4-nonadienol
• 英文别名: (2E,4Z)-2,4-dimethyl-2,4-nonadien-1-ol；(2E,4Z)-2,4-dimethylnona-2,4-dien-1-ol
• CAS: 110897-38-6
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: JAPXOJXWSRWXRO-BDLVGCLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-bromohexyne 、 Dimethylzinc 、 (E)-tert-butyl(3-iodo-2-methylallyloxy)dimethylsilane 在 双(二苯基膦苯基醚)二氯化钯(II) 二溴硼烷 、 sodium methylate 作用下， 以 二氯甲烷 、 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.67h， 以72%的产率得到(2E,4Z)-2,4-dimethyl-2,4-nonadienol
  参考文献：
  名称：

  Highly Stereo- and Regioselective Synthesis of (Z)-Trisubstituted Alkenes via 1-Bromo-1-alkyne Hydroboration−Migratory Insertion−Zn-Promoted Iodinolysis and Pd-Catalyzed Organozinc Cross-Coupling

  摘要：

  Hydroboration of 1-bromo-1-alkynes with dibromoborane followed by addition of 3 or 4 equiv of Me2Zn provides an efficient and selective route to (Z)-2-alkenyldimethylboranes (3) or (Z)-2-alkenylmethylzincs (4), respectively, which have been successfully applied to one-pot Suzuki (B-I) or Negishi (Zn-I) coupling in some less demanding cases. However, in more demanding cross-coupling reactions, only the use of either (Z)-2-alkenyliodides (5) or the alkenylzincs prepared from lithiation and then zincation of 5 proves to be highly satisfactory (Zn-II or Zn-III protocol). On the contrary, the corresponding organoboron coupling under B-II or B-III protocol appears to be less satisfactory. Preliminary studies indicate that certain substituents proximal to trisubstituted alkenes seriously affect the course of the desired alkenylboron crosscoupling.

  DOI：

  10.1021/ja0772039

文献信息

• Stereo- and Regiospecific Synthesis of Trisubstituted Alkenes via the Palladium-catalyzed Cross-coupling Reaction of Diisopropyl (<i>E</i>)-(1-Alkyl-1-alkenyl)boronates with Organic Halides
  作者：Makoto Satoh、Norio Miyaura、Akira Suzuki

  DOI：10.1246/cl.1986.1329

  日期：1986.8.5

  The reaction of diisopropyl (Z)-(1-bromo-1-alkenyl)boronates readily obtainable, with organolithiums and bases takes place readily to give (E)-(1-organo-1-alkenyl)boronates, the cross-coupling of which with various organic halides proceeds smoothly in the presence of Pd-catalyst and base to afford stereodefined trisubstituted alkenes in good yields.

  容易获得的二异丙基 (Z)-(1-溴-1-烯基) 硼酸酯与有机锂和碱的反应很容易得到 (E)-(1-有机-1-烯基) 硼酸酯，它与各种有机卤化物在钯催化剂和碱的存在下顺利进行，以良好的收率提供立体定义的三取代烯烃。
• SATOH MAKOTO; MIYAURA NORIO; SUZUKI AKIRA, CHEM. LETT.,(1986) N 8, 1329-1332
  作者：SATOH MAKOTO、 MIYAURA NORIO、 SUZUKI AKIRA

  DOI：——

  日期：——
• Highly Stereo- and Regioselective Synthesis of (<i>Z</i>)-Trisubstituted Alkenes via 1-Bromo-1-alkyne Hydroboration−Migratory Insertion−Zn-Promoted Iodinolysis and Pd-Catalyzed Organozinc Cross-Coupling
  作者：Zhihong Huang、Ei-ichi Negishi

  DOI：10.1021/ja0772039

  日期：2007.11.28

  Hydroboration of 1-bromo-1-alkynes with dibromoborane followed by addition of 3 or 4 equiv of Me2Zn provides an efficient and selective route to (Z)-2-alkenyldimethylboranes (3) or (Z)-2-alkenylmethylzincs (4), respectively, which have been successfully applied to one-pot Suzuki (B-I) or Negishi (Zn-I) coupling in some less demanding cases. However, in more demanding cross-coupling reactions, only the use of either (Z)-2-alkenyliodides (5) or the alkenylzincs prepared from lithiation and then zincation of 5 proves to be highly satisfactory (Zn-II or Zn-III protocol). On the contrary, the corresponding organoboron coupling under B-II or B-III protocol appears to be less satisfactory. Preliminary studies indicate that certain substituents proximal to trisubstituted alkenes seriously affect the course of the desired alkenylboron crosscoupling.